6-溴-2,3-二氢喹啉-4(1H)-酮 | 76228-06-3

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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: 6-溴-2,3-二氢喹啉-4(1H)-酮
• 英文名称: 6-bromo-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 6-bromo-2,3-dihydro-1H-quinolin-4-one
• CAS: 76228-06-3
• 化学式: C₉H₈BrNO
• mdl: MFCD00600620
• 分子量: 226.073
• InChiKey: WAFBCQPOMZIGTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  225-228 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• 沸点：
  359.1±42.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-2,3-dihydroquinolin-4(1h)-one
Synonyms:

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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: 6-Bromo-2,3-dihydroquinolin-4(1h)-one
CAS number: 76228-06-3

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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: C9H8BrNO
Molecular weight: 226.1

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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, 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：

  6-溴-2,3-二氢喹啉-4(1H)-酮 在 硫酸 、 potassium permanganate 作用下， 以 乙腈 为溶剂， 反应 5.33h， 以86%的产率得到6-溴-4-羟基喹啉
  参考文献：
  名称：

  4-氧代-2,3-二氢喹啉类化合物的氧化方法

  摘要：

  本发明公开了4‑氧代‑2,3‑二氢喹啉类化合物的氧化方法，它以4‑氧代‑2,3‑二氢喹啉类化合物为原料，加入有机溶剂、酸化剂和氧化剂，在50~85℃下进行氧化反应，反应结束后反应液经后处理得到4‑羟基喹啉类化合物。本发明制备方法所使用的各种原料简单易得，均为工业化品，来源广泛，价格低廉；且制备方法简单、操作容易、产物收率高，相比于以往的4‑氧代‑2,3‑二氢喹啉类化合物的氧化方法更高效，且后处理较为简单的优点，对该产品的工业化尤为重要。

  公开号：

  CN108794396B
• 作为产物：
  描述：

  4 -溴- 2 - 碘苯甲胺 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氟甲磺酸 、 三氟甲苯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 6-溴-2,3-二氢喹啉-4(1H)-酮
  参考文献：
  名称：

  用于合成 2,3-二氢-4(1H)-喹诺酮类的邻苯胺基炔丙醇的超酸催化串联 Meyer-Schuster 重排/分子内加氢胺化

  摘要：

  摘要开发了一种由邻苯胺基炔丙醇合成 2,3-二氢-4(1H)-喹诺酮类的 TfOH 催化合成方法。苯环中的 N-保护基团和取代基的研究表明，可以应用不同的基团。通过控制催化剂负载量，邻苯胺基炔丙醇顺利地进行了预期的转化，以良好的产率生产 N-保护或 N-脱保护的 2,3-二氢-4 (1H)-喹诺酮。这种转化可能涉及串联的 Meyer-Schuster 重排/分子内加氢胺化反应过程。图形概要

  DOI：

  10.1080/00397911.2016.1196293

文献信息

• [EN] BENZOTHIAZOLE COMPOUNDS<br/>[FR] COMPOSÉS DE BENZOTHIAZOLE
  申请人：INST MEDICAL W & E HALL

  公开号：WO2009039553A1

  公开（公告）日：2009-04-02

  The present invention relates to benzothiazole compounds that mimic the activity of BH3 only proteins and are capable of binding to and neutralizing pro survival Bcl 2 proteins. The invention also relates to the use of such compounds in the regulation of cell death or cell survival and the treatment and/or prophylaxis of diseases or conditions associated with the deregulation of cell death or cell survival.

  本发明涉及模拟BH3-only蛋白活性并能够结合和中和促生存Bcl-2蛋白的苯并噻唑化合物。该发明还涉及利用这类化合物调节细胞死亡或细胞存活，在治疗和/或预防与细胞死亡或细胞存活失调相关的疾病或病况。
• [EN] NOVEL SUBSTITUTED TETRAHYDROQUINOLIN COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS<br/>[FR] NOUVEAUX COMPOSÉS DE TÉTRAHYDROQUINOLINE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE (IDO)
  申请人：MERCK SHARP & DOHME

  公开号：WO2019089412A1

  公开（公告）日：2019-05-09

  Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof (I). Also disclosed herein are uses of the compounds disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of the compositions in the potential treatment or prevention of an IDO-associated disease or disorder.

  本文披露了式（I）的化合物，或其药学上可接受的盐（I）。本文还披露了所述化合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。本文还披露了包含所述化合物的组合物。本文进一步披露了所述组合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。
• Small-molecule inhibitors of cathepsin L incorporating functionalized ring-fused molecular frameworks
  作者：Jiangli Song、Lindsay M. Jones、Gustavo E. Chavarria、Amanda K. Charlton-Sevcik、Adam Jantz、Audra Johansen、Liela Bayeh、Victoria Soeung、Lindsey K. Snyder、Shawn D. Lade、David J. Chaplin、Mary Lynn Trawick、Kevin G. Pinney

  DOI：10.1016/j.bmcl.2012.12.025

  日期：2013.5

  malignant tumors and plays a significant role in cancer cell invasion and migration. It is an attractive target for the development of small-molecule inhibitors, which may prove beneficial as treatment agents to limit or arrest cancer metastasis. We have previously identified a structurally diverse series of thiosemicarbazone-based inhibitors that incorporate the benzophenone and thiochromanone molecular

  组织蛋白酶L是在多种恶性肿瘤中上调的半胱氨酸蛋白酶，在癌细胞的侵袭和迁移中起重要作用。它是开发小分子抑制剂的有吸引力的目标，小分子抑制剂可能被证明是限制或阻止癌症转移的治疗剂是有益的。我们之前已经确定了一系列结构上不同的基于硫半脲酮的抑制剂，这些抑制剂结合了二苯甲酮和硫代苯并二氢吡喃酮分子支架。本文中，我们报告了这项工作的重要扩展，旨在探索具有氮原子掺入（基于二氢喹啉）和碳原子排他性（基于四氢萘）的稠合芳基-烷基环分子系统。此外，类似物还包含氧气（基于苯并二氢吡喃酮），硫（基于硫代苯并二氢吡喃酮），亚砜，抗组织蛋白酶L时，其活性最强的化合物（7-溴二氢喹啉硫代半碳zone酮48）为50 <500 nM），IC 50  = 164 nM。所评估的所有化合物均不作为组织蛋白酶B抑制剂而处于非活性状态（IC 50 > 10,000 nM），因此，对于该组织中最活跃的组织蛋白酶L抑制剂，其选择性（
• Formation of 2,3-dihydro-4(1H)-quinolones and related compounds via Fries-type acid-catalysed rearrangement of 1-arylazetidin-2-ones
  作者：Shinto Kano、Tsutomu Ebata、Shiroshi Shibuya

  DOI：10.1039/p19800002105

  日期：——

  corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N–CO fission. In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl-, 4-ethoxycarbonyl-, and 4-piperidin-2yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3dihydro-4(1H)-quinolones

  各种1-芳基氮杂环丁烷-2-酮在回流下用三氟乙酸，100°C或浓的甲磺酸处理。通过酰基迁移和N–CO裂变生成硫酸，得到相应的2,3-二氢-4（1 H）-喹诺酮。在1-（3-取代的苯基）氮杂环丁烷-2-酮的情况下，获得两个位置异构产物，即5-和7-取代的2，3-二氢-4（1H）-喹诺酮。在酸性条件下，还将4-甲基-，4-乙氧基羰基-和4-哌啶-2-基-1-芳基氮杂环丁烷-2-酮及其类似物转化为相应的2-取代的2,3-二氢-4（1 H）-喹诺酮。 。3-取代的1-苯基氮杂环丁烷-2-酮（36）和（37）被转化为呋喃[3,2- c通过应用该方法分别制得]喹啉系统（38）和（40）。
• Synthesis of 2,3-Dihydro-4(1H)-quinolones and the Corresponding 4(1H)-Quinolones via Low-Temperature Fries Rearrangement of N-Arylazetidin-2-ones
  作者：Jens Lange、Alex C. Bissember、Martin G. Banwell、Ian A. Cade

  DOI：10.1071/ch10465

  日期：——

  cyclization processes, undergo smooth Fries-rearrangement in triflic acid at 0–18°C to give the isomeric 2,3-dihydro-4(1H)-quinolones (2). Dehydrogenation of the latter compounds using 10% Pd on C in 1.0 M aqueous sodium hydroxide/propan-2-ol mixtures at ca. 82°C provides the corresponding 4(1H)-quinolones (3).

  N型未取代的氮杂环丁烷-2-酮与相关的芳基卤化物或使用Mitsunobu环化方法，可通过Goldberg–Buchwald型铜催化的偶联反应容易地制备通式1的N-氮杂环丁烷-2-酮在三氟乙酸中于0–18°C进行重排，得到异构体2,3-二氢-4（1 H）-喹诺酮（2）。后一种化合物在1.0 M氢氧化钠/丙-2-醇水溶液中，在大约50 ℃下，用10％Pd / C脱氢。在82℃下提供了相应的4（1 H）-喹诺酮（3）。