7-溴-3,4-二氢-1(2H)-喹啉甲酸叔丁基酯 | 1187932-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 7-溴-3,4-二氢-1(2H)-喹啉甲酸叔丁基酯
• 中文别名: 1-BOC-7-溴-3,4-二氢-2H-喹啉
• 英文名称: tert-butyl 7-bromo-3,4-dihydroquinoline-1(2H)-carboxylate
• 英文别名: tert-butyl 7-bromo-3,4-dihydro-2H-quinoline-1-carboxylate
• CAS: 1187932-64-4
• 化学式: C₁₄H₁₈BrNO₂
• 分子量: 312.206
• InChiKey: JOJRQDHTJFLVJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-BOC-7-Bromo-3,4-dihydro-2H-quinoline
Synonyms: 1-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydro-7-bromoquinoline

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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-7-Bromo-3,4-dihydro-2H-quinoline
CAS number: 1187932-64-4

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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: C14H18BrNO2
Molecular weight: 312.2

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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 bromide.

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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：

  7-溴-3,4-二氢-1(2H)-喹啉甲酸叔丁基酯 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基溴化铵 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 0.16h， 生成 6-(1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinolin-7-yl)picolinic acid
  参考文献：
  名称：

  Structure-Guided Rescaffolding of Selective Antagonists of BCL-X_L

  摘要：

  Because of the promise of BCL-2 antagonists in combating chronic lymphocytic leukemia (CLL) and non-Hodgkin's lymphoma (NHL), interest in additional selective antagonists of antiapoptotic proteins has grown. Beginning with a series of selective, potent BCL-X-L antagonists containing an undesirable hydrazone functionality, in silico design and X-ray crystallography were utilized to develop alternative scaffolds that retained the selectivity and potency of the starting compounds.

  DOI：

  10.1021/ml500030p
• 作为产物：
  描述：

  6-溴茚酮 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 甲基磺酰氯 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 5.5h， 生成 7-溴-3,4-二氢-1(2H)-喹啉甲酸叔丁基酯
  参考文献：
  名称：

  Structure-Guided Rescaffolding of Selective Antagonists of BCL-X_L

  摘要：

  Because of the promise of BCL-2 antagonists in combating chronic lymphocytic leukemia (CLL) and non-Hodgkin's lymphoma (NHL), interest in additional selective antagonists of antiapoptotic proteins has grown. Beginning with a series of selective, potent BCL-X-L antagonists containing an undesirable hydrazone functionality, in silico design and X-ray crystallography were utilized to develop alternative scaffolds that retained the selectivity and potency of the starting compounds.

  DOI：

  10.1021/ml500030p
• 作为试剂：
  描述：

  二碳酸二叔丁酯 、 7-溴-1,2,3,4-四氢喹啉 在 silica gel 、 乙酸乙酯 、 hexanes 、 7-溴-3,4-二氢-1(2H)-喹啉甲酸叔丁基酯 作用下， 反应 1.0h， 以to provide 1.46 g (99%) of the desired compound tert-butyl 7-bromo-3,4-dihydroquinoline-1(2H)-carboxylate (23D)的产率得到7-溴-3,4-二氢-1(2H)-喹啉甲酸叔丁基酯
  参考文献：
  名称：

  COMPOUNDS AND METHODS OF USE

  摘要：

  在一个方面，本发明提供了一种公式I的化合物，其中在公式I中，变量X1、X2a、X2b、X2c、R1、B、L、E、A和下标n的定义如本文所述。在另一个方面，本发明提供了包含公式I化合物的药物组合物，以及使用公式I化合物治疗通过表达或过度表达Bcl-2抗凋亡蛋白（例如抗凋亡Bcl-xL蛋白）的疾病和病症（例如癌症，血小板增多症等）的方法。

  公开号：

  US20140005190A1

文献信息

• INDOLE CARBOXAMIDE COMPOUNDS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20160115126A1

  公开（公告）日：2016-04-28

  Disclosed are compounds of Formula (I): or a salt thereof, wherein: X is CR 4 or N; R 1 , R 2 , R 3 , R 4 , and A are defined herein. Also disclosed are methods of using such compounds as inhibitors of Bruton's tyrosine kinase (Btk), and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

  揭示了Formula (I)的化合物： 或其盐，其中：X为CR 4 或N；R 1 ，R 2 ，R 3 ，R 4 和A在此处定义。还揭示了使用这些化合物作为Bruton's酪氨酸激酶（Btk）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、预防或减缓各种治疗领域的疾病或疾病的进展方面非常有用，如自身免疫疾病和血管疾病。
• [EN] PURINES AND METHODS OF THEIR USE<br/>[FR] PURINES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：YUMANITY THERAPEUTICS INC

  公开号：WO2021247841A1

  公开（公告）日：2021-12-09

  Disclosed are compounds useful in the treatment of neurological disorders. The compounds described herein, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological diseases.

  本文披露了在治疗神经系统疾病中有用的化合物。这些化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• Compounds and methods of use
  申请人：Genentech, Inc.

  公开号：US09067928B2

  公开（公告）日：2015-06-30

  In one aspect, the present invention provides for a compound of Formula I in which in Formula I, the variables X1, X2a, X2b, X2c, R1, B, L, E, A and the subscript n are as defined herein. In another aspect, the present invention provides for pharmaceutical compositions comprising compounds of Formula I as well as methods for using compounds of Formula I for the treatment of diseases and conditions (e.g., cancer, thrombocythemia, etc) characterized by the expression or over-expression of Bcl-2 anti-apoptotic proteins, e.g., of anti-apoptotic Bcl-xL proteins.

  在某个方面，本发明提供了一个I式化合物，其中在I式中，变量X1，X2a，X2b，X2c，R1，B，L，E，A和下标n的定义如本文所述。在另一个方面，本发明提供了包含I式化合物的药物组合物，以及使用I式化合物治疗表达或过度表达Bcl-2抗凋亡蛋白（例如抗凋亡Bcl-xL蛋白）所致的疾病和状况（例如癌症，血小板增多症等）的方法。
• [EN] COMPOUNDS AND THEIR USE IN TREATING CANCER<br/>[FR] COMPOSÉS ET LEUR UTILISATION DANS LE TRAITEMENT DU CANCER
  申请人：ASTRAZENECA AB

  公开号：WO2022069520A1

  公开（公告）日：2022-04-07

  The specification generally relates to compounds of Formula (I) and pharmaceutically acceptable salts thereof, where A, Z, Y, RA, Linker and v have any of the meanings defined herein. This specification also relates to the use of such compounds and pharmaceutically acceptable salts thereof in methods of treatment of the human or animal body, for example in the prevention or treatment of cancer. This specification also relates to processes and intermediate compounds involved in the preparation of such compounds and to pharmaceutical compositions containing them.

  本规范一般涉及到公式（I）的化合物及其药学上可接受的盐，其中A、Z、Y、RA、连接剂和v具有本规范中定义的任何含义。本规范还涉及使用这些化合物及其药学上可接受的盐在治疗人或动物体内的方法中，例如在预防或治疗癌症方面的应用。本规范还涉及到准备这些化合物所涉及的过程和中间体化合物，以及含有它们的制药组合物。
• Copper Powder and Pd(II) Salts Triggered One-Pot Aromatic Halide Homocoupling via a Radical Pathway
  作者：Chen Li、Yumeng Shi、Quan Chen、Kun Zhang、Guang Yang

  DOI：10.1021/acs.joc.2c02717

  日期：2023.2.17

  this work, a bimetallic system was demonstrated, referring to stoichiometric copper powder in the presence of a catalytic amount of Pd(OAc)2, which contributed to delivering various symmetric/asymmetric (sp2)C–(sp2)C species. It has been proposed that the coupling process might be promoted via radicals produced by redox between Cu(0) and Pd(IV) species in the heating system. Increasing examples demonstrated

  (sp 2 )C–(sp 2 )C 键形成是目标合成以及材料和药物生产中最实用的技术之一。联芳基化合物通常与芳基卤化物或拟卤化物偶联而成，需要制备有机金属试剂，效率低，原子经济性差。可以采用经典的 Ullmann 反应直接从芳族卤化物合成联芳基化合物。然而，极高的温度要求限制了该方法在制造中的使用。同时，该机制引发了经典氧化还原反应和涉及自由基的氧化还原反应之间的广泛争论。在这项工作中，展示了一种双金属系统，指的是在催化量的 Pd(OAc) 存在下的化学计量铜粉2，这有助于提供各种对称/不对称 (sp 2 )C–(sp 2 )C 物种。有人提出，耦合过程可能通过加热系统中 Cu(0) 和 Pd(IV) 物种之间的氧化还原产生的自由基来促进。越来越多的例子证明了这种方法对官能团中的芳基溴具有良好的耐受性。