菲醌 | 84-11-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 菲醌
• 中文别名: 9,10-菲醌；9,10-菲二酮；9,10-菲蒽；菲-9,10-二酮
• 英文名称: phenanthrene-9,10-quinone
• 英文别名: phenantrenequinone；9,10-phenanthrenequinone；phenanthrene-9,10-dione；phenanthrenequinone；9,10-phenanthraquinone；9,10-phenanthroquinone；9,10-dihydrophenanthrene-9,10-dione；9,10-phenanthrenedione；phenanthraquinone
• CAS: 84-11-7
• 化学式: C₁₄H₈O₂
• mdl: MFCD00001163
• 分子量: 208.216
• InChiKey: YYVYAPXYZVYDHN-UHFFFAOYSA-N

物化性质

• 熔点：
  209-212 °C(lit.)
• 沸点：
  360 °C
• 密度：
  1.405
• 闪点：
  245 °C
• 溶解度：
  水中的溶解度为7.5毫克/升
• 颜色/状态：
  Orange-red crystals
• 蒸汽压力：
  8.5X10-7 mm Hg at 25 °C (est)
• 保留指数：
  1935;362.04
• 稳定性/保质期：

  本品可通过皮肤吸收导致中毒。实验结果显示，小鼠口服最小中毒剂量为20毫克/千克（连续给药一天）。因此，操作人员应佩戴防护用品。

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

代谢

多环芳烃的K区与非K区醌都是人类胎盘NADP连接的15-羟基前列腺素脱氢酶的优秀底物。这些化合物的kcat/Km值范围从3到20 s/m。还原了甲萘醌和甲苯醌的谷胱甘肽硫醚具有相似的催化效率。此外，这些物质和某些其他谷胱甘肽硫醚是前列腺素B1氧化和多环芳烃醌还原的强效抑制剂。存在一种可能性，即多环芳烃和其他异生物质醌的潜在毒性可能通过胎盘中的氧化还原酶改变，这种酶对前列腺素来说是相对较差的底物，而胎盘组织中某些谷胱甘肽硫醚的存在可能会影响这种酶对这些醌和其他异生物质醌的还原。

Both K-region and non-K-region o-quinones of polycyclic aromatic hydrocarbons are excellent substrates for human placental NADP linked 15-hydroxyprostaglandin dehydrogenase. These compounds are reduced with kcat/Km values ranging from 3 to 20 s/m. The glutathione thioethers of menadione and toluquinone are reduced with similar catalytic efficiencies. Furthermore, these substances and certain other glutathione thioethers are potent inhibitors of prostaglandin B1 oxidation and polycyclic aromatic hydrocarbon quinone reduction. The possibility exists that the potential toxicity of quinones of polycyclic aromatic hydrocarbons and other xenobiotic substances may be altered in the placenta by an oxidoreductase for which prostaglandins are relatively poor substrates and the presence in placental tissue of certain glutathione thioethers could influence the reduction of these quinones and other xenobiotic substances by this enzyme.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中和。如果患者停止呼吸，请开始人工呼吸，最好使用需求阀复苏器、球囊阀面罩设备或口袋面罩，按训练操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果患者呕吐，让患者身体前倾或将其置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗救助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 基本治疗：建立专利气道（如有需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的干呕反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

/SRP:/ 高级治疗：对于无意识、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放"，最低流量/。如果出现低血容量的迹象，使用0.9%生理盐水（NS）或乳酸林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。使用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。 /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/替代和体外测试/ 使用滋养层细胞系JEG-3研究菲、9,10-菲醌（PHEQ）、蒽和9,10-蒽醌单独以及与铜共同作用时的细胞毒性。终点是培养物减少alAMar Blue（AB）的能力，这是能量代谢的指标，以及将羧基荧光素二醋酸乙酰氧甲基酯（CFDA AM）转化为羧基荧光素，这是膜完整性的指示。只有PHEQ引发了细胞毒性反应。PHEQ导致AB的浓度依赖性下降，但CFDA AM读数没有下降，这表明能量代谢受损。在铜的存在下，PHEQ的浓度-反应曲线向左移动，并且使用CFDA AM获得。Cu/PHEQ的协同作用归因于氧化还原循环的增加和产生的活性氧种（ROS），这会压倒抗氧化防御，首先损害能量代谢，然后是膜完整性。不透铜的螯合剂， bathocuproine，减少了PHEQ/铜的相互作用，但可渗透的螯合剂， neocuproine和铜共同作用是细胞毒性的。

/ALTERNATIVE and IN VITRO TESTS/ The trophoblast cell line, JEG-3, was used to study the cytotoxicity of phenanthrene, 9,10-phenanthrenequinone (PHEQ), anthracene, and 9,10-anthracenedione alone and with copper. The endpoints were the capacity of cultures to reduce alamar Blue (AB), a measure of energy metabolism, and to convert carboxyfluorescein diacetate acetoxymethyl ester (CFDA AM) to carboxyfluorescein, an indication of membrane integrity. Only PHEQ elicited a cytotoxic response. PHEQ caused a concentration-dependent decline in AB but not in CFDA AM readings, suggesting an impairment to energy metabolism. In the presence of copper, PHEQ concentration-response curves were shifted to the left for AB and were obtained with CFDA AM. The Cu/PHEQ synergy is attributed to an increase in redox cycling and production of reactive oxygen species (ROS), which overwhelm antioxidant defenses, damaging energy metabolism first and then membrane integrity. The impermeable copper chelator, bathocuproine, reduced the PHEQ/copper interaction, but the permeable chelator, neocuproine, and copper together were cytotoxic.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

/替代实验和体外测试/ 典型的抗氧化剂N-乙酰-L-半胱氨酸（NAC）通常能保护细胞免受活性氧种（ROS）诱导的氧化损伤。9,10-菲醌（9,10-PQ），是柴油尾气颗粒中的主要醌类物质，通过NAD(P)H：醌氧化还原酶1（NQO1）进行的两电子还原在红氧循环中产生ROS，这被认为是其细胞和遗传毒性的原因。在本研究中，我们显示NAC意外地增强了低NQO1活性的细胞中9,10-PQ的毒性。在四种人皮肤细胞系中，NQO1的表达和活性低于人腺癌细胞系A549和MCF7。在皮肤细胞中，添加NAC显著增强了9,10-PQ的细胞毒性。伴随着组蛋白H2AX磷酸化的DNA双链断裂的形成也显著增加。另一方面，在腺癌细胞中，添加NAC抑制了细胞和遗传毒性。两个对比实验：在原本低表达NQO1的CHO-K1细胞中过表达NQO1，以及通过RNAi转染在腺癌细胞系A549中敲减NQO1，也显示NAC在表达高NQO1活性的细胞系中抑制了9,10-PQ诱导的毒性，而在低NQO1活性的细胞系中增强了毒性。结果表明，NAC对9,10-PQ的细胞和遗传毒性的双重作用取决于组织特定的NQO1活性。

/ALTERNATIVE and IN VITRO TESTS/ A typical antioxidant, N-acetyl-L-cysteine (NAC) generally protects cells from oxidative damage induced by reactive oxygen species (ROS). 9,10-Phenanthrenequinone (9,10-PQ), a major quinone in diesel exhaust particles, produces ROS in redox cycling following two-electron reduction by NAD(P)H:quinone oxidoreductase 1 (NQO1), which has been considered as a cause of its cyto- and genotoxicity. In this study, we show that NAC unexpectedly augments the toxicity of 9,10-PQ in cells with low NQO1 activity. In four human skin cell lines, the expression and the activity of NQO1 were lower than in human adenocarcinoma cell lines, A549 and MCF7. In the skin cells, the cytotoxicity of 9,10-PQ was significantly enhanced by addition of NAC. The formation of DNA double strand breaks accompanying phosphorylation of histone H2AX, was also remarkably augmented. On the other hand, the cyto- and genotoxicity were suppressed by addition of NAC in the adenocarcinoma cells. Two contrasting experiments: overexpression of NQO1 in CHO-K1 cells which originally expressed low NQO1 levels, and knock-down of NQO1 in the adenocarcinoma cell line A549 by transfection of RNAi, also showed that NAC suppressed 9,10-PQ-induced toxicity in cell lines expressing high NQO1 activity and enhanced it in cell lines with low NQO1 activity. The results suggested that dual effects of NAC on the cyto- and genotoxicity of 9,10-PQ were dependent on tissue-specific NQO1 activity.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  9
• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25,S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29146990
• 危险品运输编号：
  UN3077
• 危险类别：
  9
• RTECS号：
  SF7875000
• 包装等级：
  III
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  本品应密封保存于阴凉干燥处。采用内衬塑料袋、外套编织袋的包装方式，需存放在阴凉、干燥、通风的地方，并注意防晒和防潮。请远离火种和热源，按一般化学品规定进行贮运。

SDS

Name:	Phenanthrenequinone 98% (uv-vis) Material Safety Data Sheet
Synonym:
CAS:	84-11-7

Section 1 - Chemical Product MSDS Name:Phenanthrenequinone 98% (uv-vis) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
84-11-7	Phenanthrenequinone, tech.	80%	201-515-5

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. 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. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 84-11-7: 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 protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
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: Granules
Color: orange-red
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 360 deg C
Freezing/Melting Point: 209.00 - 211.00 C
Autoignition Temperature: 630 deg C ( 1,166.00 deg F)
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Slightly soluble.
Specific Gravity/Density:
Molecular Formula: C14H8O2
Molecular Weight: 208.22

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials, dust generation, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 84-11-7: SF7875000 LD50/LC50:
Not available.
Carcinogenicity:
Phenanthrenequinone, tech. - 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
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 84-11-7: No information available.
Canada
CAS# 84-11-7 is listed on Canada's NDSL List.
CAS# 84-11-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 84-11-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

菲醌简介

天然菲醌分为邻菲醌及对菲醌两种类型。丹参含有多种菲醌衍生物，其中包括丹参醌ⅡA、丹参ⅡB、隐丹参醌、丹参酸甲酯和羟基丹参醌ⅡA等为邻醌类衍生物；丹参新醌甲、丹参新配乙、丹参新醌丙则属于对菲醌类化合物。尽管丹参配类结构上具有菲醌母核，但其生源属于二帖类，显示出抗菌和扩张冠状动脉的作用。

菲醌的性质

菲醌是一种橙黄色针状结晶。熔点为208.5-210℃，沸点超过360℃，能够升华，相对密度为1.405。它不溶于水，微溶于乙醇、苯和醋酸乙酯，并能溶于乙醚和热醋酸，在浓硫酸中溶解并呈现暗绿色。通过升华可以得到橙红色片状体。

菲醌与亚硫酸钠反应生成不稳定的亚硫酸氢盐，进一步氧化可得联苯二甲酸；还原成菲氢醌。它具有显著的抑菌能力，可用作拌种剂来防止谷物黑穗病和棉花苗期病害，并作为纸浆防腐剂使用。经氢氧化钠处理后可用于制备多效能植物生长调节剂整形素。

化学性质

菲醌为橙红色针状结晶，熔点207℃，沸点360℃，可溶于乙醇、冰醋酸、苯和硫酸，不溶于水。与亚硫酸氢钠生成的加成物可溶于水，这一特性可用于提纯菲醌。

用途 农药

• 菲醌可用作杀菌剂、拌种剂以及电子照相材料。
• 可用作光导材料、光敏阻焊剂和纸张防腐剂。

合成应用

• 用于有机合成，可生产苯绕蒽酮。

光电材料研究

菲醌作为单体，应用于光电材料的研究。

生产方法

由菲氧化制成。主要包括化学法与电解法两种：

1. 化学法：使用重铬酸钠（或钾）与菲在硫酸水溶液中进行氧化反应。
2. 电解氧化法：电解液含三氧化铬120g/L、硫酸450g/L，菲35g/L。阴极电流密度为3.75A/cm²，电解液温度控制在60-65℃之间，经过8小时的电解后进行过滤，可得所需产品。

类别 农药

菲醌属于农药类别。

毒性分级

高毒级别。

急性毒性

大鼠腹腔LD₅₀为165毫克/公斤。

储运特性

库房需通风、低温干燥，并应与食品原料分开储运。

灭火剂

推荐使用干粉、泡沫或砂土进行灭火。

反应信息

• 作为反应物：
  描述：

  菲醌 在 氢氧化钾 作用下， 生成 二氢-3-(异十二碳烯基)呋喃-2,5-二酮
  参考文献：
  名称：

  Staudinger, Chemische Berichte, 1906, vol. 39, p. 3065

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酸乙酯 在 C₈K 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到菲醌
  参考文献：
  名称：

  Hyper-acyloin condensation from simple aromatic esters to phenanthrenequinones: a new reaction of C8K

  摘要：

  DOI：

  10.1021/jo00391a065
• 作为试剂：
  描述：

  在 C₄₆H₇₀N₄O₄ 、 三乙胺 、 菲醌 、 praseodymium(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  醌引发的光催化与醚、硫醚、胺和烷烃的对映选择性吉斯自由基加成

  摘要：

  光催化对映选择性吉斯自由基与惰性 C(sp 3 )–H 键加成代表了一种从丰富的原料中合成多种增值手性分子的高效且经济有利的方法。在此，我们公开了一种醌引发的具有惰性C(sp 3 )–H键的α-取代丙烯酰胺的光催化不对称Giese自由基加成反应，通过应用简单的醌作为HAT光催化剂并结合手性N , N '-二氧化物/镨(III ）催化剂。多种醚、硫醚、硒化物、胺和烷烃可以在温和条件下顺利转化为相应的手性α-芳基酰胺衍生物，并具有令人满意的对映选择性（68个实例，高达95% ee）。基于光谱研究和控制实验，提出了醌引发的 HAT 催化循环，DFT 计算表明醌和手性路易斯酸之间的相互作用对于不对称反向氢原子转移过程中的对映体诱导至关重要。

  DOI：

  10.1021/acscatal.4c03512

文献信息

• 1,3,5-Triazapentadienes by Nucleophilic Addition to 1,3- and 1,4-Dinitriles—Sterically Constrained Examples by Incorporation into Cyclic Peripheries: Synthesis, Aggregation, and Photophysical Properties
  作者：Agnes Johanna Wrobel、Ralph Lucchesi、Birgit Wibbeling、Constantin-Gabriel Daniliuc、Roland Fröhlich、Ernst-Ulrich Würthwein

  DOI：10.1021/acs.joc.6b00126

  日期：2016.4.1

  with the two cyano groups in 1,3 or 1,4 distance. These novel compounds show very strong tendency for aggregation due to hydrogen bonding, especially to form homodimers as seen from X-ray data in the solid state. Additional hydrogen bonding generates also linear chains in the crystal. Several of the new compounds show fluorescence in solution. Quantum chemical DFT calculations were used for evaluation

  由于主要的n /π*相互作用，1,3,5-三氮杂戊二烯通常在N–C–N–C–N骨架上呈U形或扭曲的S形构象。但是，如果1,3,5-三氮杂戊二烯单元是环的一部分，则其W构象可能仅限于平面。在这里，我们描述了13个新的1,3,5- triazapentadienes合成10 - 12，它们在空间上通过掺入抑制成六元或七元环系统，通过加入锂化的伯胺或肼的5到二腈7，8或9两个氰基的距离为1,3或1,4。这些新型化合物由于氢键而显示出非常强的聚集趋势，尤其是从固态X射线数据可以看出，它们形成同二聚体。额外的氢键还在晶体中产生线性链。几种新化合物在溶液中显示荧光。量子化学DFT计算用于评估二聚能和光物理性质的解释。
• Fused imidazoles as potential chemical scaffolds for inhibition of heat shock protein 70 and induction of apoptosis. Synthesis and biological evaluation of phenanthro[9,10-d]imidazoles and imidazo[4,5-f][1,10]phenanthrolines
  作者：Alpa Patel、Swee Y. Sharp、Katelan Hall、William Lewis、Malcolm F. G. Stevens、Paul Workman、Christopher J. Moody

  DOI：10.1039/c6ob00471g

  日期：——

  Fused imidazoles inhibit growth of human cancer cell lines, and the Hsp70 pathway in cells, and induce apoptosis.

  融合咪唑类化合物抑制人类癌细胞系的生长，影响细胞中的Hsp70途径，并诱导凋亡。
• Synthesis and Photophysics of Dibenz[<i>a</i>,<i>c</i>]phenazine Derivatives
  作者：Leandro A. Estrada、Douglas C. Neckers

  DOI：10.1021/ol200354t

  日期：2011.7.1

  The synthesis of dipolar dibenz[a,c]phenazine (DBP) derivatives is described. The compounds possess little electronic communication between donor and acceptor units in the ground state regardless of the pattern of substitution. The dipolar derivatives deactivate mostly via electron transfer (eT) under polar conditions. Intersystem crossing is likely to compete for S1 relaxation.

  描述了偶极二苯并[ a，c ]吩嗪（DBP）衍生物的合成。不管取代的模式如何，化合物在基态的供体和受体单元之间几乎没有电子通信。偶极衍生物主要在极性条件下通过电子转移（e T）失活。系统间交叉可能会竞争S 1松弛。
• White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
  作者：Heorhii V. Humeniuk、Arnulf Rosspeintner、Giuseppe Licari、Vasyl Kilin、Luigi Bonacina、Eric Vauthey、Naomi Sakai、Stefan Matile

  DOI：10.1002/anie.201804662

  日期：2018.8.13

  Bent N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine amphiphiles are introduced as mechanosensitive membrane probes that operate by an unprecedented mechanism, namely, unbending in the excited state as opposed to the previously reported untwisting in the ground and twisting in the excited state. Their dual emission from bent or “closed” and planarized or “open” excited states is shown to discriminate between

  弯曲的N,N'-二苯基-二氢二苯并[a,c]吩嗪两亲物被引入作为机械敏感膜探针，其通过前所未有的机制工作，即在激发态下不弯曲，而不是之前报道的在地面中不扭曲和在室温下扭曲。兴奋状态。它们从弯曲或“闭合”和平面化或“开放”激发态的双重发射被证明可以区分水中的胶束和固序（S o ）、液体无序（L d ）和本体膜中的单体。双发射光谱覆盖了足够的可见光范围，以产生发出带有比例编码信息的白光的囊泡。报告了通过扩展 π 系统和助色团来改善弯曲机械载体的策略，并证明了与双光子激发荧光 (TPEF) 显微镜对巨型单层囊泡中膜域成像的兼容性。
• Darstellung einiger substituierter Triphthaloyl-benzole als Ausgangsmaterialien für grüne Küpenfarbstoffe
  作者：H. E. Fierz-David、L. Blangey、W. Von Krannichfeldt

  DOI：10.1002/hlca.19470300317

  日期：1947.4.30

  Durch Kondensation entsprechend substituierter 1,4-Naphtho-chinone mittels Pyridin wurden das α-Trichlor-, α, α′-Hexachlor-, α- und β-Triacetamino- sowie das β-Trimethoxy-triphthaloyl-benzol neu hergestellt.

  通过将适当取代的1，4-萘醌与吡啶缩合，新制备了α-三氯-，α，α'-六氯-，α-和β-三乙酰氨基和β-三甲氧基-三邻苯二甲酰苯。

表征谱图