吲哚-5-甲酸乙酯 | 32996-16-0

• 物质功能分类: 医药中间体 - 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-5-甲酸乙酯
• 中文别名: 5-吲哚甲酸乙酯；吲哚-5-羧酸乙酯
• 英文名称: ethyl indole-5-carboxylate
• 英文别名: ethyl 1H-indole-5-carboxylate；1H-indole-5-carboxylic acid ethyl ester
• CAS: 32996-16-0
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: PDXPRWCJESNIIT-UHFFFAOYSA-N

物化性质

• 熔点：
  96.5-97.5 °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)：
  2.9
• 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

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl indole-5-carboxylate
Synonyms:

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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-5-carboxylate
CAS number: 32996-16-0

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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, refrigerated.
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

制备方法与用途

化学性质：类白色粉末。

反应信息

• 作为反应物：
  描述：

  吲哚-5-甲酸乙酯 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 sodium hydride 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 氯苯 、 苯 为溶剂， 反应 13.5h， 生成 5-异氰酰基-1-甲基-1H-吲哚
  参考文献：
  名称：

  Synthesis of Highly Substituted Indole Alkaloid Species via [4+1] Cyclization of Nucleophilic Carbenes and Indole Isocyanates

  摘要：

  DOI：

  10.3987/com-05-s(t)38
• 作为产物：
  描述：

  苯佐卡因 在 bis-triphenylphosphine-palladium(II) chloride 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer copper(l) iodide 、 potassium carbonate 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 二乙胺 、 calcium carbonate 、 三(4-氟苯基)磷化氢 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 吲哚-5-甲酸乙酯
  参考文献：
  名称：

  铑催化的环异构化：吲哚，苯并呋喃和烯醇内酯的形成。

  摘要：

  DOI：

  10.1002/anie.200604183

文献信息

• Analogs of indole-3-carbinol metabolites as chemotherapeutic and chemopreventive agents
  申请人：——

  公开号：US20040043965A1

  公开（公告）日：2004-03-04

  Novel compounds useful as chemotherapeutic and chemopreventive agents are provided. The compounds are analogs of indole-3-carbinol metabolites wherein the structures and substituents of the compounds are selected to enhance the compounds' overall efficacy, particularly with respect to therapeutic activity, oral bioavailability, long-term safety, patient tolerability, and therapeutic window. The compounds are useful not only in treatment of cancer but also in prevention of cancer. One preferred class of the novel compounds have the structure of formula (I) 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 are defined herein. Pharmaceutical compositions are provided as well, as are methods of synthesis and use.

  提供了作为化疗和化学预防剂有用的新化合物。这些化合物是吲哚-3-甲醇代谢物的类似物，其中化合物的结构和取代基被选择以增强化合物的整体功效，特别是在治疗活性、口服生物利用度、长期安全性、患者耐受性和治疗窗口方面。这些化合物不仅在癌症治疗中有用，而且在癌症预防中也有用。一类首选的新化合物具有以下结构式（I） 1 其中R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 和R 12 在此定义。还提供了药物组合物，以及合成和使用方法。
• 一种无过渡金属参与的吲哚β位烷基化方法
  申请人：江苏科技大学

  公开号：CN112479970A

  公开（公告）日：2021-03-12

  本发明公开一种无过渡金属参与的吲哚β位烷基化方法，该方法是以碳酸钠等碱作为催化剂，芳基烯烃作为烷基化试剂，醇作为质子化试剂提供质子，直接选择性烷基化未被保护吲哚β位，一步生成β‑烷基吲哚化合物。具体制备步骤为取吲哚衍生物、芳基烯烃、醇类溶剂和碱加入到反应器中，加热，反应通过TLC薄层色谱检测反应是否完全，待反应结束后，通过柱层析即得吲哚β位烷基化产物。本发明有益效果在于，利用商品可得碱为催化剂，非保护吲哚为底物，芳基烯烃为烷基化试剂，需要氮气保护，一步生成β‑烷基吲哚类化合物，为合成具有生物活性的β‑烷基吲哚衍生物提供了一个实用的方法，该方法操作简单、经济高效、产率高，具有重要的应用价值。
• Direct and Selective 3-Amidation of Indoles Using Electrophilic <i>N</i>-[(Benzenesulfonyl)oxy]amides
  作者：Gerardo X. Ortiz、Brett N. Hemric、Qiu Wang

  DOI：10.1021/acs.orglett.7b00358

  日期：2017.3.17

  Selective C–H amidation of 1H-indoles at the C3 position is reported as a direct entry to biologically important 3-aminoindoles. This transformation is achieved using novel N-[(benzenesulfonyl)oxy]amides as electrophilic nitrogen agents in the presence of ZnCl2. Interestingly, analogous reactions in the absence of ZnCl2 resulted in the formation of indole aminal products.

  据报道，在C3位置上1 H吲哚的选择性C–H酰胺化是直接进入具有生物学重要性的3-氨基吲哚的。在ZnCl 2存在下，使用新型N -[（苯磺酰基）氧基]酰胺作为亲电氮试剂可以实现这种转化。有趣的是，在没有ZnCl 2的情况下的类似反应导致吲哚氨基产物的形成。
• Novel 6-5 Fused Ring Heterocycle Antifolates with Potent Antitumor Activity: Bridge Modifications and Heterocyclic Benzoyl Isosters of 2,4-Diamino-6,7-dihydro-5H-cyclopenta(d)pyrimidine Antifolate.
  作者：Yoshihiko KOTAKE、Tatsuo OKAUCHI、Atsumi IIJIMA、Kentaro YOSHIMATSU、Hiroaki NOMURA

  DOI：10.1248/cpb.43.829

  日期：——

  tumor cell growth, N-[4-[3-(2,4-diamino-6,7-dihydro-5H-cyclopenta[d]pyrimidin-5- yl)propyl]benzoyl]-L-glutamic acid (1), have led to the synthesis of new cyclopenta[d]pyrimidine-based antifolates, including those with low alkyl substituted trimethylene bridges (2a, b) and isosterically modified bridges (ethyleneoxa, 2c; ethyleneamino, 2d; the N-methyl- and N-ethyl derivatives of 2d, 2e, f) and those

  结构强大的二氢叶酸还原酶（DHFR）活性和肿瘤细胞生长抑制剂N- [4- [3-（2,4-diamino-6,7-dihydro-5H-cyclopenta [d] pyrimidin-5-] （1）导致了新的基于环戊达[d]嘧啶的抗叶酸的合成，包括具有低烷基取代的亚丙基桥键（2a，b）和等位修饰桥键的化合物（亚乙基氧； 2c；亚乙基氨基2d； 2d，2e，f）的N-甲基和N-乙基衍生物以及其中1的苯环已被杂环等排物取代的化合物（吲哚，2g；二氢吲哚，2h；噻吩， 2i）。这些新的类似物作为DHFR和细胞生长抑制剂非常有效，在暴露于72小时的药物后，它们比甲氨蝶呤（MTX）和10-乙基-10-去氮杂蝶呤（10-EDAM）更有效地抑制肿瘤细胞的生长（对P388 MTX敏感和对MTX耐药，结肠26和KB） 。其中2a（1的10-甲基衍生物）和2i最有效，其效力比10-EDAM高2至3倍。药物暴
• Noncovalent Interactions in Ir-Catalyzed C–H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
  作者：Md Emdadul Hoque、Ranjana Bisht、Chabush Haldar、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.7b04490

  日期：2017.6.14

  An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented

  描述了一种用于芳族酯的对位选择性硼化的有效策略。为了获得高的对位选择性，已经开发了一种新的催化体系，该体系改变了联吡啶的核心结构。有人提出，L型配体对于通过非共价相互作用识别酯羰基的氧原子的功能至关重要，这为超选择性C–H活化/硼化提供了空前的控制因素。