3,4-二氢-2H-1,5-苯并二噁平-7-甲醛 | 67869-90-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,4-二氢-2H-1,5-苯并二噁平-7-甲醛
• 英文名称: 3,4-dihydro-2H-benzo[b][1,4]dioxepine-7-carbaldehyde
• 英文别名: 7-formyl-1,5-benzodioxepane；3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde
• CAS: 67869-90-3
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD01893356
• 分子量: 178.188
• InChiKey: LCSVYSVGXQQHSI-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2932999099

SDS

Name:	3 4-Dihydro-2h-1 5-benzodioxepine-7-carbaldehyde 95+% Material Safety Data Sheet
Synonym:
CAS:	67869-90-3

Section 1 - Chemical Product MSDS Name:3 4-Dihydro-2h-1 5-benzodioxepine-7-carbaldehyde 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
67869-90-3	3,4-Dihydro-2H-1,5-benzodioxepine-7-ca	95+%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 67869-90-3: Personal Protective Equipment Eyes: Not available.
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: Liquid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 120 - 122 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H10O3
Molecular Weight: 178.19

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 67869-90-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dihydro-2H-1,5-benzodioxepine-7-carbaldehyde - Not listed by ACGIH, IARC, or NTP.

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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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 67869-90-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 67869-90-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 67869-90-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-1,5-苯并二噁平-7-甲醛 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 3,4-dihydro-2H-1,5-benzodioxepine-7-formaldehydoxime
  参考文献：
  名称：

  设计，合成和评估新型4-苯胺基喹唑啉和取代三唑之间作为有效细胞毒性剂的杂种

  摘要：

  在此研究了几个系列新颖二氧化环的稠合的4-苯胺（10A-d ）和4-苯胺基-取代的三唑杂化化合物（11 - 14）已经被设计和合成。通过体外评估其抗癌活性突出了它们的生物学意义，其中几种化合物显示出针对三种人类癌细胞系（KB，表皮样癌； HepG2，肝癌； SK-Lu-1，非小细胞肺癌）的优异活性。特别地，与厄洛替尼相比，化合物13a显示出高达100倍的更高的细胞毒性。对接最具细胞毒性的化合物（11d，13a，13b，和14c）插入不同EGFR酪氨酸激酶结构域的ATP结合位点，以预测这些化合物与EGFR靶标的类似结合模式。

  DOI：

  10.1016/j.bmcl.2018.10.016
• 作为产物：
  描述：

  1,3-二溴丙烷 、 3,4-二羟基苯甲醛 在 potassium carbonate 作用下， 生成 3,4-二氢-2H-1,5-苯并二噁平-7-甲醛
  参考文献：
  名称：

  Structural Optimization of Caffeoyl Salicylate Scaffold as NO Production Inhibitors

  摘要：

  氯原酸（CGA）被认为是多种药用植物中重要的活性成分之一。最近，我们的研究小组证明了衍生自CGA的咖啡酰水杨酸骨架可以用于开发新型抗炎药物。最活跃的化合物D104可以成为进一步结构优化的一个非常有前景的起点。我们设计、合成并通过初步生物评估评估了一系列新型咖啡酰水杨酸类似物。获得的结果显示，两个化合物B12和B13不仅能够有效抑制脂多糖（LPS）诱导的RAW264.7细胞中一氧化氮（NO）的生成，而且在体外细胞毒性测试中安全性较高，与D104可比。对过氧化物酶体增殖物激活受体γ（PPARγ）蛋白的分子对接研究表明，化合物B12和B13与D104具有相同的结合模式，而咖啡酰水杨酸骨架的羧基可能在与蛋白质靶点的相互作用中发挥关键作用，这意味着在进一步优化时应保留羧基。

  DOI：

  10.1248/cpb.c19-00366

文献信息

• Design, synthesis, in vitro and in silico investigation of aldose reductase inhibitory effects of new thiazole-based compounds
  作者：Belgin Sever、Mehlika Dilek Altıntop、Yeliz Demir、Gülşen Akalın Çiftçi、Şükrü Beydemir、Ahmet Özdemir

  DOI：10.1016/j.bioorg.2020.104110

  日期：2020.9

  In the current study, new 4-aryl-2-[2-((3,4-dihydro-2H-1,5-benzodioxepine-7-yl)methylene)hydrazinyl]thiazole derivatives (1–12) were synthesized and screened for their inhibitory effects on AR which was purified by diverse chromatographic methods with a yield of 1.40% and a specific activity of 2.00 EU/mg. All compounds were determined as promising AR inhibitors with the Ki values in the range of 0

  醛糖还原酶（AR）催化多元醇途径中依赖NADPH的葡萄糖还原为山梨糖醇，这在糖尿病并发症的发展中起重要作用，包括白内障，视网膜病变，肾病和神经病。AR被认为是治愈这些长期糖尿病并发症的重要目标，因此，开发新的AR抑制剂是现代药物化学中的重要方法。在当前的研究中，新的4-芳基-2- [2-（（（3,4-二氢-2 H -1,5-苯并二氧杂庚烷-7-基）亚甲基）肼基]噻唑衍生物（1 – 12合成）并筛选其对AR的抑制作用，其通过多种色谱方法纯化，收率为1.40％，比活性为2.00EU / mg。与槲皮素相比，所有化合物均被确定为有前途的AR抑制剂，其K i值在0.018±  0.005μM -3.746± 1.321μM范围内（K i = 7.025±1.780μM）。尤其是，检测到的最多的是4-（4-氰基苯基）-2- [2-（（（3,4-二氢-2 H -1,5-苯并二氧杂庚-7-基）亚甲基）肼
• A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis
  作者：Jason Siu、Ian R. Baxendale、Russell A. Lewthwaite、Steven V. Ley

  DOI：10.1039/b503778f

  日期：——

  In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic ‘catch and release’ methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods.

  本文旨在报道通过一种基于合成不活跃的双吡啶螯合标签的通用“捕获与释放”方法，实现的一系列便捷的化学转化和纯化。该方法可以选择性地利用树脂结合的铜(II)物种来捕获双吡啶螯合标签。采用这种方法，我们能够获得与固相合成和支持试剂法相关的许多相同益处。
• 4,5-Dihydropyrazole derivatives containing oxygen-bearing heterocycles as potential telomerase inhibitors with anticancer activity
  作者：Yin Luo、Yang Zhou、Jie Fu、Hai-Liang Zhu

  DOI：10.1039/c4ra02200a

  日期：——

  Telomere and telomerase were closely related to the occurrence and development of some cancers. After the key active site of telomerase was identified, to enhance the ability of dihydropyrazole derivatives to inhibit telomerase, we designed a series of novel 4,5-dihydropyrazole derivatives containing heterocyclic oxygen moiety based on previous studies. The telomerase inhibition assay showed that compound 10a displayed the most potent inhibitory activity with an IC50 value of 0.6 μM for telomerase. The antiproliferative assay showed that 10a exhibited high activity against human gastric cancer cell SGC-7901 with an IC50 value of 10.95 ± 0.60 μM. Flow cytometric analysis and western blot results showed that 10a induced both apoptosis and autophagy. A docking simulation showed that 10a could bind well to the active site of telomerase and act as a telomerase inhibitor. The 3D-QSAR model was also built to provide a more pharmacological understanding that could be used to design new agents with more potent telomerase inhibitory activity.

  端粒和端粒酶与某些癌症的发生发展密切相关。在鉴定出端粒酶关键活性部位后，基于以往的研究，为了增强二氢吡唑衍生物抑制端粒酶的能力，我们设计了一系列含有杂环氧基的新型4,5-二氢吡唑衍生物。端粒酶抑制实验表明，化合物10a显示出最强的抑制活性，其对端粒酶的IC50值为0.6 μM。细胞增殖实验表明，10a对胃癌细胞SGC-7901具有很高的活性，其IC50值为10.95 ± 0.60 μM。流式细胞分析和western blot结果显示，10a可诱导细胞凋亡和自噬。对接模拟显示，10a可与端粒酶的活性位点很好地结合，并作为端粒酶抑制剂发挥作用。同时，为了能更好地指导设计出新的具有更强端粒酶抑制活性的化合物，我们构建了三维定量构效关系(3D-QSAR)模型。
• [EN] HYDRAZONE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS D'HYDRAZONE ET LEUR UTILISATION
  申请人：STEIN PHILIP

  公开号：WO2010132615A1

  公开（公告）日：2010-11-18

  The present invention relates to hydrazone compounds of Formula I: (I) and pharmaceutically acceptable salts and stereoisomers thereof, wherein R1, R2, R3, R4, L1, and L2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

  本发明涉及式I的腙化合物：(I)及其药用可接受的盐和立体异构体，其中R1、R2、R3、R4、L1和L2的定义如规范中所述。该发明还涉及将式I的化合物用作TRPM5蛋白的抑制剂。
• Discovery of 6-substituted 4-anilinoquinazolines with dioxygenated rings as novel EGFR tyrosine kinase inhibitors
  作者：Dong-Dong Li、Fei Fang、Jing-Ran Li、Qian-Ru Du、Jian Sun、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2012.07.079

  日期：2012.9

  It had been reported that some dioxygenated rings fusing with the quinazoline scaffold could lead to new EGFR inhibitors. Based on this, several kinds of oxygenated alkane quinazoline derivatives were synthetized and evaluated as EGFR inhibitors. Their antiproliferative activities were tested against four cancer cell lines: A431, MCF-7, A549, and B16-F10. Most derivatives could counteract EGF-induced

  据报道，一些与喹唑啉支架融合的双加氧环可能会导致新的EGFR抑制剂。基于此，合成了几种氧化的烷烃喹唑啉衍生物，并评价其为EGFR抑制剂。测试了它们对四种癌细胞系的抗增殖活性：A431，MCF-7，A549和B16-F10。大多数衍生物可以抵消EGF诱导的EGFR磷酸化，其效价与参考化合物厄洛替尼相当。稠合的双加氧环的大小对于生物活性至关重要，并且七原子环衍生物19在酶促测定和细胞测定中均显示出强大的体外抑制活性。