1-BOC-5-氰基吲哚 | 475102-10-4

• 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: 1-BOC-5-氰基吲哚
• 英文名称: tert-butyl 5-cyano-1H-indole-1-carboxylate
• 英文别名: 1-Boc-5-cyanoindole；tert-butyl 5-cyanoindole-1-carboxylate
• CAS: 475102-10-4
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: OYPSWAHXXPMBGM-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C(Solv: ethanol (64-17-5); hexane (110-54-3))
• 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：
  0.29
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 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：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-5-cyanoindole
Synonyms: tert-Butyl 5-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-5-cyanoindole
CAS number: 475102-10-4

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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, 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-5-氰基吲哚 在 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.5h， 生成 tert-butyl 5-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-1H-indole-1-carboxylate
  参考文献：
  名称：

  A Concise Synthesis of a Novel Antiangiogenic Tyrosine Kinase Inhibitor

  摘要：

  An efficient synthesis of the potent KDR inhibitor 3-[5-[[4-(methylsulfonyl)-1-piperazinyl]methyl]-1H-indole-2-yl]quinolin-2(1H)-one (1) is described. The process features a noncryogenic indole boronation and a dicyclohexylamine-mediated Suzuki coupling.

  DOI：

  10.1021/jo048334k
• 作为产物：
  描述：

  5-氰基吲哚 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 1-BOC-5-氰基吲哚
  参考文献：
  名称：

  Photoredox-catalyzed intermolecular dearomative trifluoromethylcarboxylation of indoles and heteroanalogues with CO₂ and fluorinated radical precursors

  摘要：

  通过光还原催化的分子间脱芳香三氟甲基羧化和/或二氟甲基羧化反应，使用CO2和含氟自由基前体反应，得到了一系列高产率的多官能团苯并杂环化合物。

  DOI：

  10.1039/d2gc03000d

文献信息

• [EN] INDOLYL-THIENO`3,4-B!PYRAZIN-3-ONE DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS AND DISEASES ASSOCIATED WITH ANGIOGENESIS<br/>[FR] DERIVES D'INDOLYL-THIENO`3,4-B!PYRAZIN-3-ONE UTILISES POUR TRAITER LES MALADIES ET LES TROUBLES HYPER-PROLIFERATIFS ASSOCIES A L'ANGIOGENESE
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2005051957A1

  公开（公告）日：2005-06-09

  This invention relates to a compound of Formula (I): (I) and its use in treating hyper-proliferative disorders and diseases associated with angiogenesis.

  这项发明涉及到化合物的公式(I)：(I)及其在治疗与血管生成有关的高增殖性疾病和疾病中的应用。
• 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。
• [EN] INDOLYL PYRAZINONE DERIVATIVES USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS AND DISEASES ASSOCIATED WITH ANGIOGENESIS<br/>[FR] DERIVES D'INDOLYLE PYRAZINONE UTILES POUR LE TRAITEMENT DES MALADIES ET DES TROUBLES HYPERPROLIFERANTS ASSOCIES A L'ANGIOGENESE
  申请人：BAYER PHARMACEUTICALS CORP

  公开号：WO2004043950A1

  公开（公告）日：2004-05-27

  This invention relates to a compound of Formula I (I)and its use in treating hyper-proliferative disorders and diseases associated with angiogenesis.

  这项发明涉及一种式I（I）化合物及其在治疗与血管生成有关的高增殖性疾病和疾病中的应用。
• Streamlined Catalytic Enantioselective Synthesis of α-Substituted β,γ-Unsaturated Ketones and Either of the Corresponding Tertiary Homoallylic Alcohol Diastereomers
  作者：Juan del Pozo、Shaochen Zhang、Filippo Romiti、Shibo Xu、Ryan P. Conger、Amir H. Hoveyda

  DOI：10.1021/jacs.0c08732

  日期：2020.10.21

  applicable, practical, and scalable strategy for efficient and enantioselective synthesis of β,γ-unsaturated ketones that contain an α-stereogenic center is disclosed. Accordingly, aryl, heteroaryl, alkynyl, alkenyl, allyl, or alkyl ketones that contain an α-stereogenic carbon with an alkyl, an aryl, a benzyloxy, or a siloxy moiety can be generated from readily available starting materials and by the use of

  公开了一种广泛适用、实用且可扩展的策略，用于有效和对映选择性合成含有 α-立体中心的 β,γ-不饱和酮。因此，包含具有烷基、芳基、苄氧基或甲硅烷氧基部分的α-立构碳的芳基、杂芳基、炔基、烯基、烯丙基或烷基酮可以由易于获得的起始材料并通过使用市售原料来产生。可用手性配体的产率为 52-96%，对映体比例为 93:7 至 >99:1。为了开发新方法，确定了获得高对映选择性的条件，并且所得的 α-取代的 NH-酮亚胺（其中存在强 C=N → B(pin) 配位）在转化为衍生酮之前不会差向异构化水解。结果表明，通过与烷基-、芳基-、杂芳基-反应，酮产物可以以任何非对映体形式转化为各种高烯丙基叔醇，收率70-96%，比例为92:8至>98:2。 、烯丙基-、乙烯基-、炔基-或炔丙基-金属试剂。该方法的实用性通过提供其他所需衍生物的转化和提供超过一克的抗HIV药物rubriflordilactones
• Palladium-Catalyzed Cross-Couplings of Lithium Arylzincates with Aromatic Halides: Synthesis of Analogues of Isomeridianin G and Evaluation as GSK-3β Inhibitors
  作者：Florence Mongin、Anne Seggio、Ghislaine Priem、Floris Chevallier

  DOI：10.1055/s-0029-1217003

  日期：2009.11

  Several analogues of isomeridianin G have been synthesized using palladium-catalyzed cross-coupling reactions of lithium triorganozincates as a key step. The latter have been prepared by deprotonative lithiation followed by transmetalation using ZnCl2˙TMEDA (0.33 equiv). cross-coupling - heterocycles - palladium - zinc - lithium

  使用钯催化的三有机锌酸锂的交叉偶联反应已合成了异构体G的几种类似物。后者已被制备deprotonative锂化，随后使用的ZnCl转移金属化2 TMEDA（0.33当量）。 交叉偶联-杂环-钯-锌-锂