4-溴吲哚-2-甲酸乙酯 | 103858-52-2

• 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: 4-溴吲哚-2-甲酸乙酯
• 中文别名: 4-溴吲哚-2-羧酸乙酯；4-溴-1H-吲哚-2-甲酸乙酯
• 英文名称: ethyl 4-bromo-1H-indole-2-carboxylate
• 英文别名: 4-bromo-1H-Indole-2-carboxylic acid ethyl ester
• CAS: 103858-52-2
• 化学式: C₁₁H₁₀BrNO₂
• 分子量: 268.11
• InChiKey: KNPDUPLMXYEJAU-UHFFFAOYSA-N

物化性质

• 沸点：
  394.7±22.0 °C(Predicted)
• 密度：
  1.554

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 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

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 4-bromo-1H-indole-2-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 4-bromo-1H-indole-2-carboxylate
CAS number: 103858-52-2

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C11H10BrNO2
Molecular weight: 268.1

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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, hydrogen bromide.

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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：

  4-溴吲哚-2-甲酸乙酯 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 ethyl 4-acetyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  [EN] 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
  [FR] 6,7-DIHYDRO-4 H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIFS CONTRE LE VIRUS DE L'HÉPATITE B (VHB)

  摘要：

  本发明一般涉及抗病毒剂。具体地，本发明涉及式I的化合物，该化合物可以抑制由乙型肝炎病毒（HBV）编码的蛋白质或干扰HBV复制周期的功能，包括这种化合物的组合物、抑制HBV病毒复制的方法、治疗或预防HBV感染的方法，以及制备这些化合物的工艺和中间体。

  公开号：

  WO2020089455A1
• 作为产物：
  描述：

  2-溴-6-硝基甲苯 在 铁粉 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-溴吲哚-2-甲酸乙酯
  参考文献：
  名称：

  GluN2特异性NMDA受体甘氨酸位点激动剂AICP的改良合成路线

  摘要：

  （R）-2-氨基-3-（4-（2-乙基苯基）-1H-吲哚-2-羧酰胺基）丙酸（AICP）是N-甲基-d-天冬氨酸（NMDA）受体甘氨酸位点激动剂，在低纳摩尔范围内具有空前的高效力，并且在效力和激动剂功效方面均具有GluN2亚基依赖性药理作用[1]。在这里，我们报告了一种适用于AICP的可扩展，实用且具有成本效益的合成路线，与之前报道的路线相比，这是一种改进。这种改进的合成路线包括对氨基酸部分的通用二苯甲基酯（DPM）保护，可广泛用于合成其他氨基酸配体。在不同离子型谷氨酸受体（iGluR）类别上对AICP进行的进一步功能评估表明，AICP与正构结合位点的高亲和力结合对NMDA受体的选择性高于对AMPA和KA酸酯的受体。此外，在GluN3A上未观察到AICP的高亲和力结合，d-丝氨酸。因此，这里描述的新方法可以实现AICP的可扩展合成，用作药理学工具化合物来研究神经元NMDA受体亚型与正常脑功能和疾病的关系。

  DOI：

  10.1016/j.tetlet.2020.151653

文献信息

• Carbene‐Catalyzed Enantioselective Aromatic N‐Nucleophilic Addition of Heteroarenes to Ketones
  作者：Yonggui Liu、Guoyong Luo、Xing Yang、Shichun Jiang、Wei Xue、Yonggui Robin Chi、Zhichao Jin

  DOI：10.1002/anie.201912160

  日期：2020.1.2

  and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and

  杂芳基醛的芳族氮原子被卡宾催化剂活化以与酮亲电子试剂反应。以良好至优异的产率和光学纯度提供多功能的环状N，O-乙缩醛产物。我们的反应涉及空前的氮杂富烯型酰基唑鎓中间体的形成。各种各样的N-杂芳族醛和缺电子的酮底物可以有效地实现这种转化。通过该协议提供的几种手性N，O-乙缩醛产品表现出优异的抗青枯菌（Rsstonia solanacearum）的抗菌活性，在开发用于植物保护的新型农业化学品中具有重要的价值。
• Synthesis of C-Mannosylated Glycopeptides Enabled by Ni-Catalyzed Photoreductive Cross-Coupling Reactions
  作者：Runyu Mao、Shiyi Xi、Sayali Shah、Michael J. Roy、Alan John、James P. Lingford、Gerd Gäde、Nichollas E. Scott、Ethan D. Goddard-Borger

  DOI：10.1021/jacs.1c05567

  日期：2021.8.18

  C-mannosylated glycopeptides, which we used to map the epitope of an antibody, as well as providing the first verified synthesis of Carmo-HrTH-I, a C-mannosylated insect hormone. To complement this approach, we also performed late-stage tryptophan C-mannosylation on a diverse array of peptides, demonstrating the broad scope and utility of this methodology for preparing glycopeptides.

  色氨酸 C-甘露糖基化的生物学功能知之甚少，部分原因是缺乏制备具有这种修饰的纯糖肽和糖蛋白的方法。为了解决这个问题，需要有效和可扩展的方法来安装这种蛋白质修饰。在这里，我们描述了独特的 Ni 催化交叉偶联条件，该条件利用光催化或 Hantzsch 酯光还原剂将糖基卤化物与（杂）芳基溴化物偶联，从而使 2-溴-色氨酸及其肽类的 α-C-甘露糖基化成为可能。 (杂)芳基溴化物更普遍。我们还报告了 2-(α- d-吡喃甘露糖基) -L-色氨酸在酸存在下容易发生异构化：在制备和处理具有这种修饰的肽时必须考虑的事情。这些发展实现了 C-甘露糖基化糖肽的第一个自动固相肽合成，我们用它来绘制抗体的表位，并提供了第一个经过验证的 C-甘露糖基化昆虫激素Carmo -HrTH-I 的合成。为了补充这种方法，我们还对多种肽进行了后期色氨酸 C-甘露糖基化，证明了这种方法用于制备糖肽的广泛范围和实用性。
• Anti-obesity 1,2,3,4,10,10-a-hexahydropy razino [1,2-a] indoles
  申请人：——

  公开号：US20020035110A1

  公开（公告）日：2002-03-21

  The present invention is directed to 1,2,3,4,10,10a,-hexahydropyrazino[1,2-a] indole derivatives as well as pharmaceutically acceptable salts, solvates and esters thereof, wherein R 1 to R 8 have the significance given in claim 1 be used in the form of pharmaceutical preparations for the treatment or prevention of disorders of the central nervous system, damage to the central nervous system, cardiovascular disorders, gastrointestinal disorders, diabetes insipidus, obesity and sleep apnea.

  本发明涉及1,2,3,4,10,10a,-六氢吡唑[1,2-a]吲哚衍生物以及药用可接受的盐、溶剂合物和酯，其中R1至R8具有如权利要求1中所述的意义，用于以药物制剂的形式治疗或预防中枢神经系统疾病、中枢神经系统损伤、心血管疾病、胃肠疾病、尿崩症、肥胖和睡眠呼吸暂停。
• [EN] NOVEL, HIGHLY ACTIVE PYRAZOLO-PIPERIDINE SUBSTITUTED INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)<br/>[FR] NOUVEAUX INDOLE-2-CARBOXAMIDES À SUBSTITUTION PYRAZOLO-PIPÉRIDINE HAUTEMENT ACTIFS AGISSANT CONTRE LE VIRUS DE L'HÉPATITE B (VHB)
  申请人：AICURIS GMBH & CO KG

  公开号：WO2019086142A1

  公开（公告）日：2019-05-09

  The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.

  本发明一般涉及新型抗病毒药剂。具体地，本发明涉及能够抑制乙型肝炎病毒（HBV）编码的蛋白质或干扰HBV复制周期功能的化合物，包含这种化合物的组合物，抑制HBV病毒复制的方法，治疗或预防HBV感染的方法，以及制备这些化合物的工艺和中间体。
• [EN] NOVEL 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)<br/>[FR] NOUVEAUX 6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE INDOLE-2-CARBOXAMIDES ACTIFS CONTRE LE VIRUS DE L'HÉPATITE B (VHB)
  申请人：AICURIS GMBH & CO KG

  公开号：WO2020089453A1

  公开（公告）日：2020-05-07

  The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for mating the compounds.

  本发明一般涉及新型抗病毒药剂。具体地，本发明涉及能够抑制乙型肝炎病毒（HBV）编码的蛋白质或干扰HBV复制周期功能的化合物，包含这种化合物的组合物，抑制HBV病毒复制的方法，治疗或预防HBV感染的方法，以及配制这些化合物的工艺和中间体。