(R)-1-(4-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone | 1335883-11-8

• 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
• 英文名称: (R)-1-(4-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone
• 英文别名: 1-[(4R)-4-amino-3,4-dihydro-2H-quinolin-1-yl]ethanone
• CAS: 1335883-11-8
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: UBTOHKCMZLCVOK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone 在 吡啶 、 copper diacetate 、 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.0h， 生成 (R)-1-(4-((4-(3-aminoprop-1-yn-1-yl)phenyl)amino)-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one
  参考文献：
  名称：

  [EN] PROPARGYL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THAT MODULATE BRD4
  [FR] COMPOSÉS PROPARGYLIQUES ET COMPOSITIONS PHARMACEUTIQUES QUI MODULENT BRD4

  摘要：

  Disclosed are compounds of formula I, formula I-1, or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof that are useful for modulating or degrading bromodomain (e.g., BRD4).

  公开号：

  WO2023196512A1
• 作为产物：
  描述：

  (R)-1-(4-azido-3,4-dihydroquinolin-1(2H)-yl)ethanone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以71%的产率得到(R)-1-(4-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone
  参考文献：
  名称：

  Novozyme 435 lipase mediated enantioselective kinetic resolution: a facile method for the synthesis of chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol derivatives

  摘要：

  Vinyl 2-chloroacetate was used as an efficient acyl donor for enantioselective acylation of racemic 1,2,3,4-tetrahydroquinolin-4-ols and 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ols with Novozyme 435 lipase. Two enantiocomplimentary tetrahydroquinolin-4-ol or tetrahydro-1H-benzo[b]azepin-5-ol derivatives could be smoothly obtained in good to excellent yields and ee values at the same time. Noteworthily, large scale preparation experiment was also demonstrated when amplified the reaction system to 10 g scale experiment, and products were obtained with high yields and ee values. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.066

文献信息

• Discovery of dehydro-oxopiperazine acetamides as novel bradykinin B1 receptor antagonists with enhanced in vitro potency
  作者：Wenyuan Qian、Jian Jeffrey Chen、Jason Human、Toshihiro Aya、Jiawang Zhu、Kaustav Biswas、Tanya Peterkin、Randall W. Hungate、Leyla Arik、Eileen Johnson、Gondi Kumar、Smriti Joseph、Janan Jona、Hong-Xun Guo、Zufan Wu

  DOI：10.1016/j.bmcl.2011.11.112

  日期：2012.1

  In a series of bradykinin B1 antagonists, we discovered that replacement of oxopiperazine acetamides with dehydro-oxopiperazine acetamides provided compounds with enhanced activity against the B1 receptor. The synthesis and SAR leading to potent analogs with reduced molecular weight will be discussed. (C) 2011 Published by Elsevier Ltd.
• Novozyme 435 lipase mediated enantioselective kinetic resolution: a facile method for the synthesis of chiral tetrahydroquinolin-4-ol and tetrahydro-1H-benzo[b]azepin-5-ol derivatives
  作者：Xiaojian Zhou、Daijun Zheng、Baodong Cui、Wenyong Han、Yongzheng Chen

  DOI：10.1016/j.tet.2015.05.066

  日期：2015.7

  Vinyl 2-chloroacetate was used as an efficient acyl donor for enantioselective acylation of racemic 1,2,3,4-tetrahydroquinolin-4-ols and 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ols with Novozyme 435 lipase. Two enantiocomplimentary tetrahydroquinolin-4-ol or tetrahydro-1H-benzo[b]azepin-5-ol derivatives could be smoothly obtained in good to excellent yields and ee values at the same time. Noteworthily, large scale preparation experiment was also demonstrated when amplified the reaction system to 10 g scale experiment, and products were obtained with high yields and ee values. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] PROPARGYL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THAT MODULATE BRD4<br/>[FR] COMPOSÉS PROPARGYLIQUES ET COMPOSITIONS PHARMACEUTIQUES QUI MODULENT BRD4
  申请人：[en]PLEXIUM, INC.

  公开号：WO2023196512A1

  公开（公告）日：2023-10-12

  Disclosed are compounds of formula I, formula I-1, or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof that are useful for modulating or degrading bromodomain (e.g., BRD4).