1-BOC-6-氰基吲哚 | 889676-34-0

• 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-氰基吲哚
• 英文名称: tert-butyl 6-cyano-1H-indole-1-carboxylate
• 英文别名: 1-Boc-6-cyanoindole；tert-butyl 6-cyanoindole-1-carboxylate
• CAS: 889676-34-0
• 化学式: C₁₄H₁₄N₂O₂
• mdl: MFCD08436020
• 分子量: 242.277
• InChiKey: DCIWEPSVBLICSS-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126
• 沸点：
  386.4±34.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-6-cyanoindole
Synonyms: tert-Butyl 6-cyano-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-cyanoindole
CAS number: 889676-34-0

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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: C14H14N2O2
Molecular weight: 242.3

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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：

  1-BOC-6-氰基吲哚 在 四(三苯基膦)钯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 2,5-bis(6-cyanoindol-2-yl)pyridine
  参考文献：
  名称：

  Synthesis and structure-activity relationship of novel bisindole amidines active against MDR Gram-positive and Gram-negative bacteria

  摘要：

  A series of novel diamidines with N-substituents on an amidine N-atom were synthesized and evaluated for their cytotoxicity and in vitro antibacterial activity against a range of Gram-positive and Gram-negative bacterial strains. Based on structure-activity relationship, N-substituents with a branched chain and a shorter carbon chain on the amidine N-atom exhibited more promising activity against Gram-negative and MDR-Gram-positive bacteria: compounds 5c and Si were the most powerful candidate compounds. Compound 5c showed greater efficacy than levofloxacin against most drug resistant Gram-positive bacteria and exhibited broad-spectrum antibacterial activity against Gram-negative bacteria, with MIC values in the range of 2-16 mu g/mL. Slightly more potent antibacterial activity against Klebsiella pneumoniae, Acinetobacter calcoaceticus, Enterobacter cloacae, and Proteus mirabilis was observed for 5i in comparison with 5c. Compound 5i also showed remarkable antibacterial activity against NDM-1-producing Gram-negative bacteria, with MIC values in the range of 2-4 mu g/mL, and was superior to the reference drugs meropenem and levofloxacin. Effective antibacterial activity of 5i was also shown in vivo in a mouse model of Staphylococcus aureus MRSA strain, with an ED(50)values of 2.62 mg/kg. (C) 2018 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2018.03.031
• 作为产物：
  描述：

  1-Boc-6-氰基吲哚-2-硼酸 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 3-氟溴苄 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 1-BOC-6-氰基吲哚
  参考文献：
  名称：

  Palladium-catalyzed benzylation of N-Boc indole boronic acids

  摘要：

  The direct benzylation of indole 2-boronic acid can be efficiently achieved using trans-PdBr-(N-Succ)(PPh(3))(2), alleviating the need for strong bases or toxic organotin reagents. Under these reaction conditions substituted indole-2-boronic acids and substituted benzyl bromides are cross-coupled to afford aryl(indolo)methanes in good yield. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.124

文献信息

• Indolyne Experimental and Computational Studies: Synthetic Applications and Origins of Selectivities of Nucleophilic Additions
  作者：G-Yoon J. Im、Sarah M. Bronner、Adam E. Goetz、Robert S. Paton、Paul H.-Y. Cheong、K. N. Houk、Neil K. Garg

  DOI：10.1021/ja1086485

  日期：2010.12.22

  conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with varying degrees of regioselectivity; distortion energies control regioselectivity and provide a simple model to predict the regioselectivity in the nucleophilic additions to indolynes and other unsymmetrical arynes. This model

  4,5-、5,6- 和 6,7-吲哚炔前体的有效合成从商业上可获得的羟基吲哚衍生物开始已有报道。合成路线是通用的，并允许获得在吡咯环上保持未取代的吲哚炔前体。Indolynes 可以在温和的氟化物介导的条件下生成，被各种亲核试剂捕获，并用于获取许多新型取代的吲哚。吲哚的亲核加成反应具有不同程度的区域选择性；畸变能控制区域选择性，并提供一个简单的模型来预测吲哚和其他不对称芳烃的亲核加成中的区域选择性。该模型导致设计出具有增强的亲核区域选择性的取代 4,5-吲哚炔。
• Exploration of DAPI analogues: Synthesis, antitrypanosomal activity, DNA binding and fluorescence properties
  作者：Abdelbasset A. Farahat、Arvind Kumar、Martial Say、Tanja Wenzler、Reto Brun、Ananya Paul、W. David Wilson、David W. Boykin

  DOI：10.1016/j.ejmech.2017.01.037

  日期：2017.3

  heteroaryl rings. Twelve amidines were synthesized and their DNA binding, fluorescence properties, in vitro and in vivo activities were evaluated. These compounds are shown to bind in the DNA minor groove with high affinity, and exhibit superior in vitro antitrypanosomal activity to that of DAPI. Six new diamidines (5b, 5c, 5d, 5e, 5f and 5j) exhibit superior in vivo activity to that of DAPI and four

  DAPI 结构已通过用取代的苯基或杂芳基环取代苯基进行了修饰。合成了 12 种脒，并评估了它们的 DNA 结合、荧光特性、体外和体内活性。这些化合物以高亲和力结合在 DNA 小沟中，并表现出优于DAPI 的体外抗锥虫活性。六种新的二脒（5b、5c、5d、5e、5f和5j）表现出优于DAPI 的体内活性，其中四种化合物在 4 × 5 mg/kg ip 的低剂量下在T中提供 100% 的动物治愈。b. 罗得西亚感染的小鼠。一般来说，新类似物的荧光特性不如 DAPI，但化合物5i除外，其显示功效适度增加，而化合物5k与 DAPI 相当。
• [EN] 2-ARYL OR HETEROARYL INDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLE 2-ARYLE OU HÉTÉROARYLE
  申请人：MERCK & CO INC

  公开号：WO2009042092A1

  公开（公告）日：2009-04-02

  The present invention provides 2-aryl or heteroaryl indole derivatives which are ASIC channel modulators, pharmaceutical compositions containing such compounds, and methods of using them as therapeutic agents.

  本发明提供了2-芳基或杂环芳基吲哚衍生物，其为ASIC通道调节剂，包含这些化合物的药物组合物，以及将它们用作治疗剂的方法。
• Synthesis of New Substituted 2-(Trimethylstannyl)indoles
  作者：David Boykin、Arvind Kumar、Martial Say

  DOI：10.1055/s-2008-1032162

  日期：2008.3

  Synthesis of the previously unreported 2-(trimethylstannyl)indole derivatives, 5-bromo-1-(tert-butoxycarbonyl)-2-(tri­methylstannyl)-1H-indole, 6-bromo-1-(tert-butoxycarbonyl)-2-(tri­-methylstannyl)-1H-indole, 1-(tert-butoxycarbonyl)-2-(trimethylstannyl)-1H-indole-5-carbonitrile, 1-(tert-butoxycarbonyl)-2-(trimethylstannyl)-1H-indole-6-carbonitrile and 1-(tert-butoxy­-carbonyl)-2-(trimethylstannyl)-1H-pyrrolo[2,3-b]pyridine-6-carbo­nitrile, is described.

  合成以前未报道的 2-(三甲基锡)吲哚衍生物，5-溴-1-(叔丁氧羰基)-2-(三甲基锡)-1H-吲哚，6-溴-1-(叔丁氧羰基)-2-(三甲基锡)-1H-吲哚、描述了 1-(叔丁氧羰基)-2-(三甲基锡基)-1H-吲哚-5-甲腈、1-(叔丁氧羰基)-2-(三甲基锡基)-1H-吲哚-6-甲腈和 1-(叔丁氧羰基)-2-(三甲基锡基)-1H-吡咯并[2,3-b]吡啶-6-甲腈。
• 2-ARYL OR HETEROARYL INDOLE DERIVATIVES
  申请人：Chang Ronald K.

  公开号：US20100197657A1

  公开（公告）日：2010-08-05

  The present invention provides 2-aryl or heteroaryl indole derivatives which are ASIC channel modulators, maceutical compositions containing such compounds, and methods of using them as therapeutic agents.

  本发明提供了2-芳基或杂环芳基吲哚衍生物，这些衍生物是ASIC通道调节剂，包含这种化合物的医药组合物，并将其用作治疗剂的方法。