1-BOC-6-氯吲哚 | 323580-68-3

• 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: 1-BOC-6-氯吲哚
• 中文别名: 6-氯吲哚-1-羧酸叔丁酯
• 英文名称: tert-butyl 6-chloro-1H-indole-1-carboxylate
• 英文别名: 1-Boc-6-chloroindole；tert-butyl 6-chloroindole-1-carboxylate
• CAS: 323580-68-3
• 化学式: C₁₃H₁₄ClNO₂
• 分子量: 251.713
• InChiKey: UEXNCLFRKGJYDV-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87
• 密度：
  1.19

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-6-chloroindole
Synonyms: tert-Butyl 6-chloro-1H-indole-1-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: 1-BOC-6-chloroindole
CAS number: 323580-68-3

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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: C13H14ClNO2
Molecular weight: 251.7

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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 chloride.

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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：

  1-BOC-6-氯吲哚 在 硼酸三异丙酯 、 lithium diisopropyl amide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 1-BOC-6-氯吲哚-2-硼酸
  参考文献：
  名称：

  WO2006/81343

  摘要：

  公开号：
• 作为产物：
  描述：

  氨基甲酸叔丁酯 、 1-bromo-2-[2-bromovinyl]-5-chlorobenzene 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以84%的产率得到1-BOC-6-氯吲哚
  参考文献：
  名称：

  Palladium catalyzed tandem alkenyl- and aryl-C–N bond formation: a cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles

  摘要：

  A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared: carbamates, anilines and amines can be employed as the N-nucleophile. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.046

文献信息

• Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- and C3-Borylated Indolines
  作者：Grace L. Trammel、Rositha Kuniyil、Phillip F. Crook、Peng Liu、M. Kevin Brown

  DOI：10.1021/jacs.1c05902

  日期：2021.10.13

  the C2- or C3-positions. Synthetically useful C2- and C3-borylated indolines can be accessed through a simple change in N-protecting group in high regio- and diastereoselectivities (up to >40:1 rr and >40:1 dr) from readily available starting materials. Additionally, the origin of regioselectivity was explored experimentally and computationally to uncover the remarkable interplay between carbonyl orientation

  吲哚脱芳构化是获取二氢吲哚的重要策略：二氢吲哚是存在于多种天然产物和生物活性分子中的基序。本文提出了一种过渡金属催化吲哚区域选择性脱芳香芳基硼化反应生成多种二氢吲哚的方法。该方法通过在 C2-或 C3-位置上缺乏激活或导向基团的底物上的迁移插入途径实现简单吲哚的分子间脱芳构化。合成有用的 C2- 和 C3- 硼酸化二氢吲哚可以通过简单改变N-保护基团以高区域选择性和非对映选择性（高达 >40:1 rr 和 >40:1 dr）从容易获得的起始材料获得。此外，通过实验和计算探索了区域选择性的起源，以揭示吲哚上N保护基团的羰基取向、C2-C3 π 键的电子和空间之间的显着相互作用。该方法首次实现了 (−)-azamedicarpin 的对映选择性合成。
• Substituted oxoazaheterocyclyl compounds
  申请人：AVENTIS PHARMACEUTICALS INC.

  公开号：US20040102450A1

  公开（公告）日：2004-05-27

  This invention is directed to oxoazaheterocycyl compounds which inhibit Factor Xa, to oxoazaheterocycyl compounds which inhibit both Factor Xa and Factor IIa, to pharmaceutical compositions comprising these compounds, to intermediates useful for preparing these compounds, to a method of directly inhibiting Factor Xa and to a method of simultaneously directly inhibiting Factor Xa and Factor IIa..

  这项发明涉及抑制因子Xa的氧杂杂环化合物，抑制同时抑制因子Xa和因子IIa的氧杂杂环化合物，包含这些化合物的药物组合物，用于制备这些化合物的中间体，直接抑制因子Xa的方法，以及同时直接抑制因子Xa和因子IIa的方法。
• Stereoselective Palladium-Catalyzed Carboaminoxylations of Indoles with Arylboronic Acids and TEMPO
  作者：Sylvia Kirchberg、Roland Fröhlich、Armido Studer

  DOI：10.1002/anie.200901072

  日期：2009.5.25

  Indoles are not indolent: Various indoles react with arylboronic acids chemodivergently. CH arylation of free indole and N‐methylindole gives the corresponding C(2)‐arylated indoles A whereas N‐acylated, N‐benzoylated, and N‐Boc‐protected indoles provide the corresponding arylcarboaminoxylated products B with excellent diastereoselectivity in good to excellent yields.

  吲哚不是惰性的：各种吲哚与芳基硼酸发生化学扩散反应。Ç 游离的吲哚及H芳基化Ñ甲基吲得到相应的C（2）吲哚-arylated甲而N-酰基化，N-苯甲酰化，和N-Boc保护的吲哚提供相应arylcarboaminoxylated产品乙与良好优秀非对映选择性至优异的产量。
• Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles
  作者：Kai Liu、Guangyang Xu、Jiangtao Sun

  DOI：10.1039/c7sc04086e

  日期：——

  excellent Z-selectivity, demonstrating unusual reactivity and selectivity compared with other noble metal catalysis. Importantly, simply followed by silica gel adsorption, an unprecedented metal-free aerobic oxidation occurs for indoles bearing N-electron donating substituents, providing a novel and efficient approach towards 3-substituted indolin-2-ones with a newly formed quaternary stereocenter in

  已经通过阳离子金（I）催化开发了重氮化合物使吲哚空前的脱芳香化作用。功能化选择性地发生在C3位置，以高收率和优异的Z传递亚甲基吲哚衍生物-选择性，与其他贵金属催化相比，显示出不同寻常的反应性和选择性。重要的是，简单地进行硅胶吸附之后，带有N电子给体取代基的吲哚会发生前所未有的无金属需氧氧化，从而为新颖的季铵立体中心具有优异立体选择性的3-取代的吲哚-2-酮提供了一种新颖而有效的方法。 。值得注意的是，这些方法提供了从丰富的原料化学物质中直接和选择性地获得各种有价值的中间体的途径。
• 一种醛固酮合酶调节剂中间体的制备方法
  申请人：重庆博腾制药科技股份有限公司

  公开号：CN104530000B

  公开（公告）日：2016-07-20

  本发明公开了一种醛固酮合酶调节剂中间体的制备方法，其步骤为将Boc保护下的反应底物在氯化氢和乙醇中反应上缩醛保护，不分离直接加热脱除Boc保护，然后进行N?甲基化反应得到N?甲基化产物，不分离直接脱缩醛保护，得到目标产物。本发明的路线反应转化率高，产物纯度高，可以有效保证产品质量，并且能实现车间生产。