二苯并噻吩 | 132-65-0

• 物质功能分类: 化学试剂 - 有机试剂 - 三环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 二苯并噻吩
• 中文别名: 二苯噻吩；二苯并噻吩/硫芴；硫芴
• 英文名称: dibenzothiophene
• 英文别名: Dibenzothiophen；DBT；dibenzo[b,d]thiophene
• CAS: 132-65-0
• 化学式: C₁₂H₈S
• mdl: MFCD00004969
• 分子量: 184.262
• InChiKey: IYYZUPMFVPLQIF-UHFFFAOYSA-N

物化性质

• 熔点：
  97-100 °C (lit.)
• 沸点：
  332-333 °C (lit.)
• 密度：
  1.1410 (rough estimate)
• 闪点：
  170 °C
• 溶解度：
  0.0015g/l（升）
• LogP：
  4.380
• 颜色/状态：
  Colorless crystals
• 蒸汽压力：
  2.05X10-4 mm Hg at 25 °C /extrapolated/
• 大气OH速率常数：
  8.10e-12 cm3/molecule*sec
• 分解：
  When heated to decomposition it emits toxic vapors of /sulfur oxide/.
• 保留指数：
  1741.9;1766;1728;1724;1742;1717;1739.8;1728;1733.1;1722;1719;1732.2;1721;1720.9;295.77;295.95;295.9
• 稳定性/保质期：
  基本性质：无色或白色针状结晶，易溶于乙醇和苯，也能溶于水和乙醚。熔点为97～100℃，沸点为332～333℃。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

当贝杰林克菌B8/36在存在二苯并噻吩的情况下与琥珀酸一起培养时，培养介质中积累了(+)-顺式-1,2-二羟基-1,2-二氢二苯并噻吩和二苯并噻吩-5-氧化物。每种代谢物都以结晶形式分离并经多种化学技术鉴定，从假单胞菌putida分离的顺式-萘二氢二醇脱氢酶将(+)-顺式-1,2-二羟基-1,2-二氢二苯并噻吩氧化为一种暂时被识别为1,2-二羟基二苯并噻吩的化合物。

Beijerinckia B8/36 when grown with succinate in the presence of dibenzothiophene, accumulated (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene and dibenzothiophene-5-oxide in the culture medium. Each metabolite was isolated in crystalline form and characterized by a variety of chemical techniques, cis-Naphthalene dihydrodiol dehydrogenase, isolated from Pseudomonas putida, oxidized (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene to a compound that was tentatively identified as 1,2-dihydroxydibenzothiophene. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

DBT微生物转化在潜在脱硫方面具有意义。作者分离出三种土壤假单胞菌，将DBT氧化成特有的水溶性含硫产物。其中两个分离株含有一个55-md的质粒；在诺氟沙星的存在下生长导致质粒丢失和氧化DBT的能力丧失。重新引入质粒恢复了氧化DBT为水溶性产物的能力。DBT氧化的产物被表征，包括3-羟基-2-甲酰基苯并噻吩、3-氧代-[3'-羟基-噻纳芬基-(2)-亚甲基]-二氢噻纳芬和4-[2-(3-羟基)-噻纳芬基]-2-氧代-3-丁烯酸的半缩醛和反式形式。DBT氧化的产物抑制了细胞生长和进一步的DBT氧化。我们的土壤分离株中DBT氧化被萘或水杨酸诱导，在很小程度上被DBT诱导，并且被琥珀酸抑制。

The microbial transformation of dibenzothiophene (DBT) is of interest in the potential desulfurization of oil. /The authors/ isolated three soil Pseudomonas species which oxidized DBT to characteristic water-soluble, sulfur-containing products. Two of /the/ isolates harbored a 55-megadalton plasmid; growth in the presence of novobiocin resulted in both loss of the plasmid and loss of the ability to oxidize DBT. Reintroduction of the plasmid restored the ability to oxidize DBT to water-soluble products. The products resulting from the oxidation of DBT were characterized and included 3-hydroxy-2-formyl benzothiophene, 3-oxo-[3'-hydroxy-thionaphthenyl-(2)-methylene]-dihydrothionaph thene, and the hemiacetal and trans forms of 4-[2-(3-hydroxy)-thianaphthenyl]-2-oxo-3-butenoic acid. The products of DBT oxidation were inhibitory to cell growth and further DBT oxidation. DBT oxidation in our soil isolates was induced by naphthalene or salicylate and to a much lesser extent by DBT and was repressed by succinate.

来源:Hazardous Substances Data Bank (HSDB)

代谢

各种微生物被筛选出它们通过一种特定的硫途径脱硫二苯并噻吩（DBT）的能力。根据脱硫活性，G3菌株被选为最佳菌株。从分类学研究中，该菌株被归类为分枝杆菌属。二苯并噻吩可以被该菌株的生长细胞和静止细胞降解，并且检测到2-羟基联苯作为终极产物。G3菌株还可以脱硫4,6-二甲基DBT。硫酸根离子抑制了DBT脱硫酶（s）的表达。2-羟基联苯的积累对细胞生长和DBT脱硫都产生了严重的抑制作用。该菌株的静止细胞可以在12小时内脱硫大约250 ppm的DBT或4,6-二甲基DBT。

Various microorganisms were screened for their ability to desulfurize dibenzothiophene (DBT) via a sulfur-specific pathway. Based on the desulfurization activity, strain G3 was selected as the best strain. From taxonomical studies, the strain was shown to belong to the genus Mycobacterium. Dibenzothiophene was degraded by both growing and resting cells of this strain, and 2-hydroxybiphenyl was detected as a dead-end product. Strain G3 could also desulfurize 4,6-dimethylDBT. Sulfate ion repressed the expression of the DBT desulfurizing enzyme(s). Accumulation of 2-hydroxybiphenyl produced severe inhibitory effects on both cell growth and DBT desulfurization. Resting cells of this strain could desulfurize about 250 ppm of DBT or 4,6-dimethylDBT within 12 hr.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在厌氧条件下，使用从土壤中分离出的硫酸盐还原菌Desulfovibrio desulfuricans M6研究了有机硫化合物的微生物降解。联苯是二苯并噻吩降解的主要产物。

The microbial degradation of organic sulfur compounds was studied in the anaerobic conditions using Desulfovibrio desulfuricans M6, a sulfate-reducing bacterium isolated from soil. Biphenyl was the major dibenzothiophene degradation product.

来源:Hazardous Substances Data Bank (HSDB)

代谢

多环芳烃（PAH）芴的代谢途径以及Sphingomonas sp. LB126对多环芳烃菲、荧蒽、蒽和二苯并噻吩的共代谢途径进行了研究。对于二苯并噻吩，鉴定出了代谢物二苯并噻吩-5-氧化物和二苯并噻吩-5,5-二氧化物；这些化合物似乎是死胡同途径的产物。由于除了二苯并噻吩之外，其他底物的代谢物浓度并没有非常高，因此推测即使是菲、荧蒽和蒽的共代谢降解，也会发生完全降解。

The metabolic pathway of the PAH fluorene and the cometabolic pathway of the PAHs phenanthrene, fluoranthene, anthracene and dibenzothiophene in Sphingomonas sp. LB126 were examined. ...For dibenzothiophene the metabolites dibenzothiophene-5-oxide and dibenzothiophene-5,5-dioxide were identified; these compounds appeared to be the products of a dead-end pathway. Since apart from dibenzothiophene no metabolites were found in very high concentrations for any of the other substrates, complete degradation is suggested, even for the cometabolic degradation of phenanthrene, fluoranthene and anthracene.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：二苯并噻吩

IARC Carcinogenic Agent:Dibenzothiophene

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专论：第103卷（2013年）：沥青及其排放物，以及一些N-和S-杂环芳香烃

IARC Monographs:Volume 103: (2013) Bitumens and Bitumen Emissions, and some N- and S-Heterocyclic Aromatic Hydrocarbons

来源:International Agency for Research on Cancer (IARC)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素

Neurotoxin - Other CNS neurotoxin

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

多环芳烃（PAHs）的杂环衍生物通常是环境污染物混合物中的重要组成部分；然而，它们对这些混合物毒性的贡献并没有很好地被描述。这些杂环在含有芳烃受体（AHR）激动剂的PAH混合物中常见。这些研究的目的是探讨两种PAH杂环化合物，咔唑（CB）和二苯并噻吩（DBT），单独以及与AHR的PAH型激动剂（β-萘黄酮[BNF]）联合使用时，对AHR介导的细胞色素P4501A（CYP1A）活性和鱼胚胎毒性的影响。Fundulus heteroclitus的胚胎暴露于CB或DBT，以及是否与BNF共同暴露。咔唑单独略微诱导，而DBT单独略微降低，与对照值相比，在卵内CYP1A介导的乙氧基还原素-O-脱乙基酶（EROD）活性。然而，暴露于CB或DBT会降低在卵内共同暴露于BNF的胚胎的EROD活性。咔唑和DBT在体外被定性为非竞争性CYP1A抑制剂。尽管咔唑和DBT单独使用时并没有胚胎毒性，但它们增强了BNF的胚胎毒性。在受污染的生态系统中，CB和DBT与PAH型AHR诱导剂的共同出现可能会增加这些环境中PAH型AHR激动剂的毒性，这在估计PAH混合物的胚胎毒性时可能需要被考虑。

Heterocyclic derivatives of polycyclic aromatic hydrocarbons (PAHs) are often significant components of environmental contaminant mixtures; however, their contribution to the toxicity of these mixtures is not well characterized. These heterocycles commonly co-occur in PAH mixtures, which contain agonists for the aryl hydrocarbon receptor (AHR). /The/ goal for these studies was to explore the effects of two PAH heterocycles, carbazole (CB) and dibenzothiophene (DBT), alone and in combination with a PAH-type agonist for the AHR (beta-naphthoflavone [BNF]) on AHR-mediated cytochrome P4501A (CYP1A) activity and on fish embryotoxicity. Embryos of Fundulus heteroclitus were exposed to CB or DBT, with and without coexposure to BNE Carbazole alone slightly induced, whereas DBT alone slightly reduced, in ovo CYP1A-mediated ethoxyresorufin-O-deethylase (EROD) activity compared to control values. However, exposure to CB or DBT reduced in ovo EROD activity in embryos coexposed to BNE Carbazole and DBT were characterized in vitro as noncompetitive CYP1A inhibitors. Carbazole and DBT enhanced the embryotoxicity of BNF, although neither compound was embryotoxic by itself. The co-occurrence of CB and DBT with PAH-type AHR inducers in contaminated ecosystems may increase the toxicity of PAH-type AHR agonists in these settings and may need to be considered when estimating the embryotoxicity of PAH mixtures.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

400克的大彩虹鳟鱼（rainbow trout）被暴露在添加了四种多环芳烃化合物（PACs）的食物颗粒中。在5、10、15和19周后，分析了肌肉、肝脏、内脏、脂肪组织和血液中的PAC、脂质和水分含量。在所有的收集时间点，以每克为基础表达的浓度在脂肪组织和内脏中最 高，其次是肝脏和肌肉，血液中观察到最低水平。当检查组织负担时，咔唑、二苯并呋喃、二苯并噻吩和芴的最高生物积累在肌肉和内脏中，脂肪组织中居中，血液和肝脏中最低。具有最低对数K(OW)的咔唑在任何组织中的浓度最低。组织中的水平与对数K(OW)显著相关（> 5%的显著性水平），尤其是在较长的暴露时间下，当检查肌肉、脂肪组织和内脏时相关性更高（> 0.05%）。不同的组织显示出不同的时间趋势，器官之间的比率有助于确定暴露时间的长度。随着时间的推移，在内部器官相对于其他组织的水平变化最为显著，尤其是与每日暴露相比。还比较了通过粪便和胆囊胆汁排除污染物的情况，因为它们代表了评估最近暴露的额外工具。

Large rainbow trout (400 g) were exposed to food pellets spiked with four polycyclic aromatic compounds (PACs). Muscle, liver, internal organs, fatty tissue, and blood were analyzed after 5, 10, 15, and 19 weeks for PAC, lipid, and moisture content. At all collection times, concentrations expressed on a per gram basis were higher in fatty tissue and internal organs, followed by liver and muscle, and lowest levels were observed in blood. When examining the tissue burden, the highest bioaccumulations of carbazole, dibenzofuran, dibenzothiophene, and fluorene were in muscle and internal organs, intermediate in fatty tissue, and lowest in blood and liver. Carbazole with the lowest log K(OW) showed the lowest concentration within any tissue. Levels in tissues were significantly correlated to log K(OW) (> 5% level of significance), especially with longer exposure, and were more highly correlated when examining muscle, fatty tissue, and internal organs (> 0.05%). Different tissues displayed different time trends, and ratios between organs help determine the length of exposure. The most striking change in levels observed with time was in internal organs relative to other tissues, particularly when compared to daily exposure. The elimination of contaminants in feces and gallbladder bile was also compared, because they represent additional tools to assess recent exposure.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  9
• 危险品标志：
  Xn
• 安全说明：
  S36
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险品运输编号：
  2811
• 危险类别：
  9
• RTECS号：
  HQ3490550
• 包装等级：
  III
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  贮存于阴凉处密封保存。

SDS

Name:	Dibenzothiophene 99% Material Safety Data Sheet
Synonym:	2,2'-Biphenylylene sulfide; 9-Thiafluorene; Dibenzo(b,d)thiophene; Diphenylene sulfide
CAS:	132-65-0

Section 1 - Chemical Product MSDS Name:Dibenzothiophene 99% Material Safety Data Sheet
Synonym:2,2'-Biphenylylene sulfide; 9-Thiafluorene; Dibenzo(b,d)thiophene; Diphenylene sulfide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
132-65-0	Dibenzothiophene	99	205-072-9

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
Harmful if swallowed. Causes gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
May cause respiratory tract irritation.
Chronic:
Chronic ingestion may cause liver damage.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid breathing dust.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 132-65-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: yellow to green
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 332 - 333 deg C @ 760 mm Hg
Freezing/Melting Point: 97 - 100 deg C
Autoignition Temperature: > 450 deg C (> 842.00 deg F)
Flash Point: 170 deg C ( 338.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C12H8S
Molecular Weight: 184.26

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 132-65-0: HQ3490550 LD50/LC50:
CAS# 132-65-0: Oral, mouse: LD50 = 470 mg/kg.
Carcinogenicity:
Dibenzothiophene - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 132-65-0: No information available.
Canada
CAS# 132-65-0 is listed on Canada's DSL List.
CAS# 132-65-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 132-65-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

二苯并噻吩及其烷基衍生物(DBTs)被认为是柴油馏分中最难脱硫的硫化物之一，是柴油加氢脱硫研究的重要模型化合物。因此，使用二苯并噻吩、4-MDBT和4,6-DMDBT作为模型化合物进行油品深度脱硫的研究成为当前国内外的一个热点。此外，二苯并噻吩还可作为玫瑰香型香料的助剂。

制备方法

将2-[5-(4-二苯并[b,d]噻吩基)]噻吩醛、氰基乙酸甲酯和六氢哌啶按照物质的量比（19-21）：（21-23）：1加入反应容器中，再滴加无水甲苯，在105-115℃下搅拌反应5-7小时。反应结束后，浓缩去除有机溶剂，并过滤取滤饼。随后使用氯仿和石油醚的混合溶剂进行重结晶，即可得到目标产物。

生物活性

二苯并噻吩是一种由两个苯环稠合到一个中心噻吩环上的有机合成中间体。

反应信息

• 作为反应物：
  描述：

  二苯并噻吩 在 LiCrH4*2LiCl*2THF 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以24%的产率得到联苯
  参考文献：
  名称：

  有机金属化学试剂没有有机金属化学试剂：亚价早期过渡金属盐的调制电子转移反应

  摘要：

  低价，早期过渡金属试剂在有机化学中作为选择性还原剂的潜力已通过对McMurry反应及其众多变体中产生的不明确且不均一的亚价钛中间体的深入研究而得以预示。作为开发对有机底物具有调制和选择性活性的可溶，定义明确的过渡金属还原剂的长期研究工作的一部分，已彻底检查了可溶于THF的还原剂二氯化钛以及类似的ZrCl 2和HfCl 2试剂，通过在THF中用丁基锂对四氯化物进行烷基化还原，很容易获得所有这些试剂。值得注意的是，MCl 4的这种相互作用相反，在烃介质中用丁基锂制得的M（III）或M（IV）卤化物氢化物。应用于VCl 4，CrCl 3和MoCl 5的THF中类似的烷基化还原反应产生的还原剂与从Mcl 4获得的还原剂相似，但反应活性分级。已证明这种还原剂能够以与涉及两电子转移（TET）的氧化加成一致的方式偶联羰基衍生物，苄基卤化物，乙炔和某些烯烃。这种反应途径与观察到的由酮形成频哪醇的立体化学以及炔烃的还原性二聚化相一致。与CrCl

  DOI：

  10.1002/cber.19971300903
• 作为产物：
  描述：

  联苯 在 sulfur 、 aluminum (III) chloride 作用下， 反应 12.33h， 生成 二苯并噻吩
  参考文献：
  名称：

  一种基于4-(9H-咔唑-9-基)苯胺的双极性小 分子发光材料及其制备方法与应用

  摘要：

  本发明公开了一种基于4‑(9H‑咔唑‑9‑基)苯胺的双极性小分子发光材料及其制备方法与应用。其主要特征是以4‑(9H‑咔唑‑9‑基)苯胺为空穴传输中心单元，通过选择具有电子传输功能化的基团，获得以4‑(9H‑咔唑‑9‑基)苯胺为中心的双极性小分子。本发明所制备的双极性小分子可用于制作有机发光二极管的发光层。

  公开号：

  CN105503846B
• 作为试剂：
  描述：

  4-硝基苯乙烯 、 1,1'-bis(trimethylsilyl)-1,1'-dihydro-4,4'-bipyridine 在 二苯并噻吩 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 4-ethenyl-N,N-bis(trimethylsilyl)aniline
  参考文献：
  名称：

  有机硅还原剂对硝基芳烃进行无金属脱氧和还原二烯化反应

  摘要：

  使用N，N'-双（三甲基甲硅烷基）-4,4'-联吡啶亚烷基（1）在温和和中性的反应条件下实现了硝基芳烃的无金属脱氧和还原二甲硅烷基化反应，并且该反应可能具有广泛的官能团耐受性。单脱氧可得到合成上有价值的N，O-双（三甲基甲硅烷基）苯羟胺（7 a），是一种容易获得且安全的硝基苯来源的苯基亚硝酸，双脱氧可得到N，N-双（三甲基硅烷基）苯胺8。改变1的量很容易控制反应温度以及加入二苯并噻吩（DBTP）。2-芳基硝基苯与1的反应通过N，O-双（三甲基甲硅烷基）苯基羟胺7的热解衍生的原位生成的亚苯基硝基苯胺生成相应的咔唑14，随后将其插入分子内CH。此外，分子内的N-N偶联反应将2,2'-二硝基联苯衍生物还原1，得到相应的苯并[ c ]喹啉。

  DOI：

  10.1002/chem.201801972

文献信息

• Electrophilic Sulfonium-Promoted Peptide and Protein Amidation in Aqueous Media
  作者：Chuan Wan、Yuan Feng、Zhanfeng Hou、Chenshan Lian、Liang Zhang、Yuhao An、Jinming Sun、Dongyan Yang、Chenran Jiang、Feng Yin、Rui Wang、Zigang Li

  DOI：10.1021/acs.orglett.1c04017

  日期：2022.1.21

  A novel amidation strategy using electrophilic sulfonium, which is soluble and stable in aqueous conditions, was developed. The sulfoniums could activate thioacid and carboxyl acid to efficiently react with amines to afford amides. This method enables applications in amidation in both aqueous media and solid-phase peptide synthesis, peptide/protein modifications, and reactive lysines of a proteome

  开发了一种使用亲电锍的新型酰胺化策略，该锍在水性条件下可溶且稳定。锍可以活化硫代酸和羧酸，有效地与胺反应生成酰胺。该方法可用于水介质和固相肽合成中的酰胺化、肽/蛋白质修饰以及在 pH 10 的蛋白质组的反应性赖氨酸以及基于活性的蛋白质分析。还使用这种方法对 USP7-UBL2 结构域进行了肽配体定向标记。
• [EN] HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS<br/>[FR] MODULATEURS DU RÉCEPTEUR HORMONAL POUR LE TRAITEMENT D'ÉTATS ET DE TROUBLES MÉTABOLIQUES MUTAGÈNES ET FIBROTIQUES
  申请人：ARDELYX INC

  公开号：WO2019055808A1

  公开（公告）日：2019-03-21

  The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1, X2, Y1, Y2, Y3, Y4, R1, R2, and R3 are described herein.

  这项发明涉及FXR的激活剂，可用于治疗自身免疫性疾病、肝病、肠道疾病、肾脏疾病、癌症以及FXR发挥作用的其他疾病，其化学式为（I）：其中L1、A、X1、X2、Y1、Y2、Y3、Y4、R1、R2和R3如本文所述。
• Inhibitors of histone deacetylase
  申请人：——

  公开号：US20020177594A1

  公开（公告）日：2002-11-28

  Compounds having the formula 1 or therapeutically acceptable salts thereof, are histone deacetylase (HDAC) inhibitors. Preparation of the compounds, compositions containing the compounds, and treatment of diseases using the compounds are disclosed.

  具有以下化学式的化合物或其治疗上可接受的盐是组蛋白去乙酰化酶（HDAC）抑制剂。本文揭示了该化合物的制备、含有该化合物的组合物以及使用该化合物治疗疾病的方法。
• [EN] NOVEL TRICYCLIC COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX COMPOSES TRICYCLIQUES UTILES POUR TRAITER LES TROUBLES INFLAMMATOIRES ET ALLERGIQUES, PROCEDE DE PREPARATION DE CES COMPOSES ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2004037805A1

  公开（公告）日：2004-05-06

  The present invention relates to novel tricyclic compounds useful for the treatment of inflammatory conditions, diseases of the central nervous and insulin resistant diabetes.

  本发明涉及用于治疗炎症性疾病、中枢神经系统疾病和胰岛素抵抗性糖尿病的新型三环化合物。
• ORGANIC LIGHT EMITTING ELEMENT, DISPLAY DEVICE, IMAGE INFORMATION PROCESSING DEVICE, LIGHTING DEVICE, IMAGE FORMING DEVICE, EXPOSURE DEVICE, AND ORGANIC PHOTOELECTRIC CONVERSION ELEMENT
  申请人：CANON KABUSHIKI KAISHA

  公开号：US20170012215A1

  公开（公告）日：2017-01-12

  The present disclosure provides an organic light emitting element which has a pair of electrodes and an organic compound layer disposed therebetween and in which the organic compound layer contains an organic compound represented by the following general formula [1], wherein in the formula [1], Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group or a heteroaromatic ring group, R 1 to R 4 are each independently selected from a hydrogen atom or a substituent, R 1 and R 2 and R 3 and R 4 each may form a benzene ring, wherein the benzene ring may have at least one substituent.

  本公开提供了一种有一对电极和位于其之间的有机化合物层的有机发光元件，其中所述有机化合物层包含由下述通用式[1]表示的有机化合物， 在通用式[1]中，Ar1和Ar2分别独立表示芳香烃基或杂芳环基，R1至R4分别独立地选自氢原子或取代基，R1和R2以及R3和R4各自可以形成苯环，其中苯环可以具有至少一个取代基。

表征谱图