N-(boc)-4-氯吲哚 | 129822-46-4

• 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: N-(boc)-4-氯吲哚
• 英文名称: tert-butyl 4-chloro-1H-indole-1-carboxylate
• 英文别名: N-tert-butoxycarbonyl-4-chloroindole；4-chloro-indole-1-carboxylic acid tert-butyl ester；1-BOC-4-Chloroindole；tert-butyl 4-chloroindole-1-carboxylate
• CAS: 129822-46-4
• 化学式: C₁₃H₁₄ClNO₂
• 分子量: 251.713
• InChiKey: SNYOMIGRAXEOBR-UHFFFAOYSA-N

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

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-4-Chloroindole
Synonyms: tert-Butyl 4-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-4-Chloroindole
CAS number: 129822-46-4

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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: 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：

  N-(boc)-4-氯吲哚 在 硼酸三异丙酯 、 lithium diisopropyl amide 、 sodium hydroxide 、 Oxone 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 以70%的产率得到Tert-butyl 4-chloro-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  Conversion of 1-Boc-indoles to 1-Boc-oxindoles

  摘要：

  A facile synthesis of substituted oxindoles 2 from the corresponding indole is described. The reaction, which proceeds through the 2-(indolyl) borate intermediate, is general and applicable to several indoles. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.053
• 作为产物：
  描述：

  3-氯-2-甲基苯胺 在 盐酸 、 仲丁基锂 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 N-(boc)-4-氯吲哚
  参考文献：
  名称：

  Preparation of Indoles and Oxindoles fromN-(tert-Butoxycarbonyl)-2-alkylanilines

  摘要：

  使用双锂化的N-(叔丁氧羰基)苯胺1与二甲基甲酰胺或二氧化碳反应，可得到中间体3和5，它们分别容易转化为N-(叔丁氧羰基)吲哚4和氧化吲哚（吲哚-2(3H)-酮，7）。双锂化的1与N-甲氧基-N-甲基酰胺缩合得到酮9，这些酮在三氟乙酸处理下环化，根据反应时间的不同，形成2-取代的1-(叔丁氧羰基)吲哚10或2-取代的吲哚11。这一通用方法已被应用于高效合成1,2-烷基桥联吲哚12、1,3,4,5-四氢苯[c,d]吲哚（16）、2a,3,4,5-四氢苯[c,d]吲哚-2(1H)-酮（18）以及1-(叔丁氧羰基)-1H-吡咯并[2,3-b]吡啶（21）。

  DOI：

  10.1055/s-1991-26597

文献信息

• [EN] 1,3,5 -TRIAZINE-2-AMINE DERIVATIVES, PREPARATION THEREOF AND DIAGNOSTIC AND THERAPEUTIC USE THEREOF<br/>[FR] DÉRIVÉS DE 1,3,5-TRIAZINE-2-AMINE, PROCÉDÉ DE PRÉPARATION DE CEUX-CI ET UTILISATION DIAGNOSTIQUE ET THÉRAPEUTIQUE DE CES DÉRIVÉS
  申请人：SANOFI SA

  公开号：WO2013087643A1

  公开（公告）日：2013-06-20

  The present invention relates to compounds corresponding to formula (I) in which: - R1 represents a substituted phenyl; - R2 represents: - a substituted phenyl; - a heteroaromatic group, the said group being unsubstituted or substituted one or more times; - R3 represents a group Alk; - R4 represents a hydrogen atom or a (C1-C4)alkyl; - R5 represents a hydrogen atom, a (C3-C6)cycloalkyl or a (C1-C4)alkyl-O-Alk; - or alternatively R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from: azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl; - R6 represents a group -COOAlk, a group -CONH 2 or a group -NHSO 2 Alk; - Alk represents a (C1-C4)alkyl, which is unsubstituted or substituted one or more times with a halogen atom; in the form of the base or of an acid-addition salt. Preparation process and diagnostic and therapeutic use.

  本发明涉及与以下式（I）对应的化合物：- R1代表取代苯基；- R2代表：- 取代苯基；- 杂芳基团，所述基团未取代或取代一次或多次；- R3代表羟基烷基基团；- R4代表氢原子或（C1-C4）烷基；- R5代表氢原子，（C3-C6）环烷基或（C1-C4）烷基-O-烷基；- 或者R4和R5，连同它们连接的氮原子，构成从以下中选择的杂环基团：氮杂环丙烷-1-基，吡咯烷-1-基，哌啶-1-基，吗啉-4-基；- R6代表-羟基烷基基团，-酰胺基或-NHSO2烷基基团；- 烷基代表未取代或取代一次或多次的（C1-C4）烷基，其上带有卤原子；以碱或酸盐的形式。制备过程和诊断和治疗用途。
• Insights into the Catalytic Activity of [Pd(NHC)(cin)Cl] (NHC=IPr, IPr^Cl , IPr^Br ) Complexes in the Suzuki-Miyaura Reaction
  作者：Frédéric Izquierdo、Caroline Zinser、Yury Minenkov、David B. Cordes、Alexandra M. Z. Slawin、Luigi Cavallo、Fady Nahra、Catherine S. J. Cazin、Steven P. Nolan

  DOI：10.1002/cctc.201701279

  日期：2018.2.7

  palladium N‐heterocyclic carbene complexes and their activity in the Suzuki–Miyaura reaction were investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands (IPr=1,3‐bis(2,6‐diisopropyl‐phenyl)imidazol‐2‐ylidene; cin=cinnamyl) were synthesized. After determining the electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr) (cin)Cl]. The three

  研究了C 4,5卤代化对钯N-杂环卡宾配合物及其在Suzuki-Miyaura反应中的活性的影响。两种带有IPr Cl和IPr Br的[Pd（NHC）（cin）Cl]配合物合成了配体（IPr = 1,3-双（2,6-二异丙基-苯基）咪唑-2-亚基; cin =肉桂基）。在确定这些配体的电子和空间特性后，将它们的特性与[Pd（IPr）（cin）Cl]进行比较。通过使用DFT计算研究了三种钯配合物，以描绘它们在导致推定的12电子活性催化剂的活化步骤中的行为。通过实验，研究了它们在低催化剂负载下在Suzuki-Miyaura反应中的催化活性，该反应涉及广泛的偶联伙伴（30个条目）。
• Inherent vs Apparent Chemoselectivity in the Kumada–Corriu Cross-Coupling Reaction
  作者：XiYe Hua、Jeanne Masson-Makdissi、Ryan J. Sullivan、Stephen G. Newman

  DOI：10.1021/acs.orglett.6b02631

  日期：2016.10.21

  The Kumada–Corriu reaction is a powerful tool for C–C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent

  Kumada-Corriu反应是形成C-C键的有力工具，但由于存在化学选择性问题，因此很少使用。在本文中，我们证明了在许多亲电和杂环官能团的存在下可以发生高产率的偶联。我们的策略是基于机械的，使氧化添加速率与格氏试剂的注射泵添加速率相匹配。连续输注ESI-MS研究发现了该策略有效的机械原因。
• A trans diacyloxylation of indoles
  作者：Qiang Liu、Qing Yong Zhao、Jie Liu、Pan Wu、Hong Yi、Aiwen Lei

  DOI：10.1039/c2cc17815j

  日期：——

  A trans diacyloxylation of indoles is accomplished by employing PhI(OAc)2 as the oxidant. A broad range of functional groups are well tolerated. Both the electronic properties of the N-protecting groups of indoles and the acidity of the reaction media play important roles in the selectivity of indole acyloxylation reactions.

  通过使用PhI(OAc)2作为氧化剂，成功实现了吲哚的反式二酰氧化反应。多种功能团在反应中表现出良好的耐受性。吲哚N保护基的电子性质和反应介质的酸度在吲哚酰氧化反应的选择性中发挥了重要作用。
• NOVEL P2X7R ANTAGONISTS AND THEIR USE
  申请人：BOES MICHAEL

  公开号：US20100267762A1

  公开（公告）日：2010-10-21

  The present application is directed to novel P2X7R antagonists that are N-indol-3-yl-acetamide and N-azaindol-3-yl-acetamide compounds, pharmaceutical compositions comprising the same and their use for the prophylactic or therapeutic treatment of diseases mediated by P2X7R activity.

  本申请涉及新型P2X7R拮抗剂，即N-吲哚-3-基乙酰胺和N-氮杂吲哚-3-基乙酰胺化合物，包括这些化合物的药物组合物，以及它们用于预防或治疗由P2X7R活性介导的疾病的用途。