1-Boc-5-氰基吲哚-2-硼酸 | 475102-15-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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-2-硼酸
• 中文别名: N-叔丁氧羰基-5-氰基吲哚-2-硼酸；1-BOC-5-氰基-1H-吲哚-2-硼酸；1-BOC-5-氰基-2-硼酸；1-叔丁氧羰-5-氰基吲哚-2-硼酸
• 英文名称: (1-(tert-butoxycarbonyl)-5-cyano-1H-indol-2-yl)boronic acid
• 英文别名: 1-Boc-5-cyano-1H-indole-2-boronic acid；[5-cyano-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid
• CAS: 475102-15-9
• 化学式: C₁₄H₁₅BN₂O₄
• 分子量: 286.095
• InChiKey: AJWYBPNMPKTRDV-UHFFFAOYSA-N

物化性质

• 熔点：
  260-270
• 沸点：
  509.1±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.48
• 氢给体数：
  2.0
• 氢受体数：
  6.0

安全信息

• 危险品标志：
  Xi
• 危险性防范说明：
  P305+P351+P338,P405,P261,P280,P304+P340
• 危险性描述：
  H302,H315,H335,H319
• 储存条件：
  保持冷静

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-5-Cyanoindole-2-boronic acid
Synonyms: 5-Cyano-1-tert-butoxycarbonylindole-2-boronic acid; 1-BOC-5-Cyano-2-indoleboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 1-BOC-5-Cyanoindole-2-boronic acid
CAS number: 475102-15-9

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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, under −20◦C.
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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C14H15BN2O4
Molecular weight: 286.1

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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.

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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-2-硼酸 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Amidine derived inhibitors of acid-sensing ion channel-3 (ASIC3)

  摘要：

  A series of indole amidines modified at the 2-position of the indole ring were evaluated as inhibitors of Acid-Sensing Ion Channel-3 (ASIC3), a novel target for the treatment of chronic pain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.021
• 作为产物：
  描述：

  1-BOC-5-氰基吲哚 在 硼酸三异丙酯 、 lithium diisopropyl amide 、 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以81%的产率得到1-Boc-5-氰基吲哚-2-硼酸
  参考文献：
  名称：

  A Non-cryogenic Method for the Preparation of 2-(Indolyl) Borates, Silanes, and Silanols

  摘要：

  2-Indolyl borates are prepared via addition of LDA to a mixture of N-Boc-indole and triisopropyl borate at 0-5 degreesC. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).

  DOI：

  10.1021/jo026087j

文献信息

• Discovery and structure–activity relationship studies of indole derivatives as liver X receptor (LXR) agonists
  作者：Farid Bakir、Sunil Kher、Madhavi Pannala、Norma Wilson、Trang Nguyen、Ila Sircar、Kei Takedomi、Chiaki Fukushima、James Zapf、Kui Xu、Shao-Hui Zhang、Juping Liu、Lisa Morera、Lisa Schneider、Naoki Sakurai、Rick Jack、Jie-Fei Cheng

  DOI：10.1016/j.bmcl.2007.03.076

  日期：2007.6

  A structurally novel liver X receptor (LXR) agonist (1) was identified from internal compound collection utilizing the combination of structure-based virtual screening and high-throughput gene profiling. Compound 1 increased ABCA1 gene expression by eightfold and SREBP1c by threefold in differentiated THP-1 macrophage cell lines. Confirmation of its agonistic activity against LXR was obtained in the

  利用基于结构的虚拟筛选和高通量基因分析相结合的方法，从内部化合物收集中鉴定出一种结构新颖的肝X受体（LXR）激动剂（1）。在分化的THP-1巨噬细胞系中，化合物1使ABCA1基因表达增加了8倍，而SREBP1c增加了3倍。在辅助因子募集和报告基因反式激活测定中获得了其对LXR的激动活性的证实。描述了对化合物1的构效关系研究。
• [EN] TYROSINE KINASE INHIBITORS, COMPOSITIONS AND METHODS THERE OF<br/>[FR] INHIBITEURS DE TYROSINE KINASE, COMPOSITIONS ET PROCÉDÉS ASSOCIÉS
  申请人：BETTA PHARMACEUTICALS CO LTD

  公开号：WO2020114499A1

  公开（公告）日：2020-06-11

  The present invention relates to compounds of Formula (I), methods of using the compounds as Trk inhibitors, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating, preventing or ameliorating diseases or disorders such as cancer or infections. (I)

  本发明涉及式(I)的化合物，使用这些化合物作为Trk抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗、预防或改善癌症或感染等疾病或疾病方面是有用的。 (I)
• [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。
• [EN] NOVEL SUBSTITUTED INDOLE DERIVATIVES AS GAMMA SECRETASE MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS D'INDOLE SUBSTITUÉS UTILISÉS EN TANT QUE MODULATEURS DE LA GAMMA-SÉCRÉTASE
  申请人：JANSSEN PHARMACEUTICALS INC

  公开号：WO2013010904A1

  公开（公告）日：2013-01-24

  The present invention is concerned with novel substituted indole derivatives of Formula (I) wherein R1, R2, R3, A1, A2, A3, Y and X have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及具有以下式（I）中R1、R2、R3、A1、A2、A3、Y和X所定义含义的新型取代吲哚衍生物。根据本发明的化合物可用作γ-分泌酶调节剂。本发明还涉及制备这种新型化合物的方法，包含该化合物作为活性成分的药物组合物，以及将该化合物用作药物的用途。
• Novel indole derivatives, preparation thereof as medicinal products and pharmaceutical compositions, and especially as KDR inhibitors
  申请人：Aventis Pharma S.A.

  公开号：US20040242559A1

  公开（公告）日：2004-12-02

  The invention relates to compounds of formula (I): 1 in which R1 represents pyrazolyl or indazolyl, R2 and R3 especially represent H, halogen, hydroxyl, nitro, cyano, R4, —OR4, —COR4, —OC(═O)R4, —C(═O)OR4, —C(═O)OH, —N(R5)C(═O)R4, —N(R5)C(═O)OR4, —S(O)nR4, —S(O)nOR4, —N(R5)SO2R4, —NY1Y2, —C(═O)NY1Y2, —N(R5)C(═O)NY1Y2, —S(O)nNY1Y2 and —OC(═O)NY1Y2, R4 especially represents alkyl, alkenyl, cycloalkyl, aryl, heteroaryl and heterocycloalkyl, R5 especially represents H, alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl, Y1 and Y2 especially represent H, alkyl, alkenyl, cycloalkyl, heterocycloalkyl, aryl, arylcarboxyl, heteroaryl and heteroarylcarboxy, which are optionally substituted, or Y1 and Y2 form with N an amino ring, n represents 0 to 2, all these radicals being optionally substituted, these products being in all the isomeric forms and the salts, as medicinal products, especially as KDR inhibitors.

  该发明涉及公式（I）的化合物：其中R1代表吡唑基或吲唑基，R2和R3特别代表H、卤素、羟基、硝基、氰基、R4、—OR4、—COR4、—OC(═O)R4、—C(═O)OR4、—C(═O)OH、—N(R5)C(═O)R4、—N(R5)C(═O)OR4、—S(O)nR4、—S(O)nOR4、—N(R5)SO2R4、—NY1Y2、—C(═O)NY1Y2、—N(R5)C(═O)NY1Y2、—S(O)nNY1Y2和—OC(═O)NY1Y2，其中R4特别代表烷基、烯基、环烷基、芳基、杂芳基和杂环烷基，R5特别代表H、烷基、烯基、环烷基、杂环烷基、芳基和杂芳基，Y1和Y2特别代表H、烷基、烯基、环烷基、杂环烷基、芳基、芳基羧基、杂芳基和杂芳基羧基，可以选择地被取代，或者Y1和Y2与N形成氨基环，n代表0至2，所有这些基团都可以选择地被取代，这些产品以所有异构体形式和盐的形式作为药物产品，特别作为KDR抑制剂。