吲哚-4-甲酸乙酯 | 50614-84-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 吲哚-4-甲酸乙酯
• 英文名称: ethyl indole-4-carboxylate
• 英文别名: Ethyl 1H-indole-4-carboxylate
• CAS: 50614-84-1
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: ZIUDZKABRXGZFO-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  342.4±15.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl indole-4-carboxylate
Synonyms: Ethyl 1H-indole-4-carboxylate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Ethyl indole-4-carboxylate
CAS number: 50614-84-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H11NO2
Molecular weight: 189.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  吲哚-4-甲酸乙酯 在 potassium permanganate 、 lithium aluminium tetrahydride 、 乙醚 、 丙酮 作用下， 生成 4-吲哚甲醛
  参考文献：
  名称：

  吲哚-4-醛的生产

  摘要：

  通过用氢化铝锂还原容易从吲哚-4-羧酸得到的乙酯或甲酯，得到4-氧甲基吲哚，并通过用高锰酸钾氧化而得到吲哚-4-醛。与文献（熔点142-143°）相反，对于已知的吲哚-4-羧酸甲酯，发现熔点为64°。

  DOI：

  10.1002/hlca.19540370628
• 作为产物：
  描述：

  4-ethoxycarbonyl-1-tri-isopropylsilylindole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以88%的产率得到吲哚-4-甲酸乙酯
  参考文献：
  名称：

  通过2-（2-苯基亚磺酰基乙烯基）吡咯的合成4-酰基吲哚。

  摘要：

  通过将1-三异丙基甲硅烷基-反式-2-（2-苯基亚磺酰基乙烯基）-吡咯与缺电子的乙炔进行[4π+2π]环加成，然后将环加合物与氟离子进行N-脱甲硅烷基化反应，可以轻松获得4-环戊二烯。

  DOI：

  10.1016/s0040-4039(00)96324-x

文献信息

• HTS-based discovery and optimization of novel positive allosteric modulators of the α7 nicotinic acetylcholine receptor
  作者：István Ledneczki、Anita Horváth、Pál Tapolcsányi、János Éles、Katalin Dudás Molnár、István Vágó、András Visegrády、László Kiss、Áron Szigetvári、János Kóti、Balázs Krámos、Sándor Mahó、Patrik Holm、Sándor Kolok、László Fodor、Márta Thán、Diána Kostyalik、Ottilia Balázs、Mónika Vastag、István Greiner、György Lévay、Balázs Lendvai、Zsolt Némethy

  DOI：10.1016/j.ejmech.2021.113560

  日期：2021.10

  HTS campaign of the corporate compound collection resulted in a novel, oxalic acid diamide scaffold of α7 nACh receptor positive allosteric modulators. During the hit expansion, several derivatives, such as 4, 11, 17 demonstrated not only high in vitro potency, but also in vivo efficacy in the mouse place recognition test. The advanced hit molecule 11 was further optimized by the elimination of the

  公司化合物收集的 HTS 活动产生了一种新型的 α7 nACh 受体阳性变构调节剂草酸二酰胺支架。在命中膨胀，几个衍生物，如4，11，17证明不仅高体外效力，而且在体内在小鼠地方识别测试功效。先进的命中分子11通过消除推定的诱变芳香胺结构单元而得到进一步优化，该结构单元产生了一个新的氨基甲基吲哚化合物家族。在化合物55 的情况下发现了最平衡的物理化学和药理学特征。对接研究揭示了一个亚基间结合位点是我们的化合物最可能的。55不仅在东莨菪碱诱导的健忘症（小鼠位置识别测试）中，而且在自然遗忘（大鼠新物体识别测试）中表现出良好的认知增强特征。此外，化合物55在具有高转化价值的认知范式中是活跃的，即在大鼠触摸屏视觉辨别测试中。因此，选择55作为先导化合物进行进一步优化。基于获得的有利结果，本发明的氨基甲基吲哚簇可以通过α7 nAChR的正变构调节为认知增强提供可行的方法。
• Cascade trifluoromethylthiolation and cyclization of <i>N</i>-[(3-aryl)propioloyl]indoles
  作者：Ming-Xi Bi、Shuai Liu、Yangen Huang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.3762/bjoc.16.62

  日期：——

  A cascade oxidative trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles with AgSCF₃ is described. This protocol allows for the synthesis of novel bis(trifluoromethylthiolated) or trifluoromethylthiolated pyrrolo[1,2-a]indol-3-ones in moderate to good yields. Mechanistic investigations indicated that radical processes were probably involved in these transformations.

  描述了一种使用AgSCF₃对N-[(3-芳基)丙烯酰基]吲哚进行级联氧化三氟甲硫基化和环化的方法。这个方案允许以中等到良好的产率合成新的双(三氟甲硫基化)或三氟甲硫基化的吡咯[1,2-a]吲哚-3-酮。机理研究表明，自由基过程可能参与了这些转化。

• [EN] DIMERIC IAP INHIBITORS<br/>[FR] INHIBITEURS IAP DIMÉRIQUES
  申请人：NOVARTIS AG

  公开号：WO2012080271A1

  公开（公告）日：2012-06-21

  The present invention provides compounds of formula M-L-M' (where M and M' are each independently a monomeric moiety of Formula (I) and L is a linker). The dimeric compounds have been found to be effective in promoting apoptosis in rapidly dividing cells. (I)

  本发明提供了公式M-L-M'的化合物（其中M和M'分别独立地是公式（I）的单体基团，L是连接基团）。已发现二聚化合物在促进快速分裂细胞凋亡方面具有有效性。（I）
• A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step
  作者：Charlotte M. Griffiths-Jones (née Haskins)、David W. Knight

  DOI：10.1016/j.tet.2011.08.094

  日期：2011.11

  The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.

  吲哚生物碱α-环吡嗪酸1是通过一种途径合成的，其核心特征在于被磺酰胺基终止的酸催化的阳离子级联环化反应。
• Palladium(II) Catalyzed C–H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles
  作者：Michael S. Watt、Kevin I. Booker-Milburn

  DOI：10.1021/acs.orglett.6b02947

  日期：2016.11.4

  C–H activation offers huge potential in the generation of complex structures from simple starting materials. Herein we report the development of a highly diastereoselective palladium(II) catalyzed C–H functionalization cascade to produce novel, unsaturated polyheterocycles from simple diene-tethered heterocyclic starting materials. The reaction is applicable to both indole and pyrrole based substrates

  C–H活化在从简单的起始原料生成复杂结构方面提供了巨大的潜力。在本文中，我们报道了由非对映选择性的钯（II）催化的C–H官能化级联反应的发展，该反应由简单的由二烯系链的杂环原料生产出新颖的，不饱和的多杂环。该反应适用于基于吲哚和吡咯的底物，并能耐受杂芳族核周围的各种官能团取代。多杂环产物形成为单一的非对映异构体，并且在一个步骤中形成了两个新的立体中心。

表征谱图