8-bromo-1,2,3,5-tetrahydro-4H-cyclopenta[c]quinolin-4-one | 95515-78-9

• 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: 8-bromo-1,2,3,5-tetrahydro-4H-cyclopenta[c]quinolin-4-one
• 英文别名: 1,2,3,4-Tetrahydro-8-brom-4-oxo-1H-cyclopentachinolin；8-bromo-1,2,3,5-tetrahydro-cyclopenta[c]quinolin-4-one；8-Bromo-1,2,3,5-tetrahydrocyclopenta[c]quinolin-4-one
• CAS: 95515-78-9
• 化学式: C₁₂H₁₀BrNO
• 分子量: 264.121
• InChiKey: LNVQIIIWFGYBDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  452.3±45.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-bromo-1,2,3,5-tetrahydro-4H-cyclopenta[c]quinolin-4-one 在 四(三苯基膦)钯 N,N-二甲基丙烯基脲 、 氢氧化钾 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 12.0h， 生成 3-(3-(5-ethyl-4-oxo-2,3,4,5-tetrahydro-1H-cyclopenta[c]quinolin-8-yl)-4-trifluoromethoxyphenyl)acrylic acid tert-butyl ester
  参考文献：
  名称：

  RXR–LXR heterodimer modulators for the potential treatment of dyslipidemia

  摘要：

  A number of RXR agonists were synthesized and screened in functional assays. The synthesis and tile structure-activity relationship (SAR) within the series of compounds will be presented. Some in vivo data in rodent models for dyslipidemia and diabetes will also be presented. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.01.047
• 作为产物：
  描述：

  4-溴异氰酸苯酯 生成 8-bromo-1,2,3,5-tetrahydro-4H-cyclopenta[c]quinolin-4-one
  参考文献：
  名称：

  RXR–LXR heterodimer modulators for the potential treatment of dyslipidemia

  摘要：

  A number of RXR agonists were synthesized and screened in functional assays. The synthesis and tile structure-activity relationship (SAR) within the series of compounds will be presented. Some in vivo data in rodent models for dyslipidemia and diabetes will also be presented. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.01.047

文献信息

• A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups
  作者：Rajasekar Reddy Annapureddy、Christian Jandl、Thorsten Bach

  DOI：10.1021/jacs.0c02803

  日期：2020.4.22

  of various quinolones and pyridones. The C-H activation reaction proceeded with high site- and enantioselectivity (14 examples, 83-97% ee). Key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahy-dro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol%) served as the silver source, PhI=NNs as the nitrene precursor and 1,10- phenanthroline

  据报道，在各种喹诺酮类和吡啶酮类的脂肪族 C3 取代基上发生了银催化的胺化。CH 活化反应以高位点和对映选择性进行（14 个实例，83-97% ee）。其成功的关键是使用手性菲咯啉配体，该配体通过乙炔基接头连接到八氢-1H-4,7-methanoisoindol-1-one 的 8 位。AgPF6 (10 mol%) 作为银源，PhI=NNs 作为氮烯前体，1,10-菲咯啉作为配体。反应结果可以通过假设在氢键银络合物中插入氮烯 CH 来理解，其中单个 CH 键暴露于催化反应中心。
• AMINOALKYL-3,4-DIHYDROCHINOLIN-DERIVATE ALS NO SYNTHASE INHIBITOREN
  申请人：Schering Aktiengesellschaft

  公开号：EP1115708B1

  公开（公告）日：2004-04-14
• Dihydroquinolines as Novel n-NOS Inhibitors
  作者：Stefan Jaroch、Peter Hölscher、Hartmut Rehwinkel、Detlev Sülzle、Gerardine Burton、Margrit Hillmann、Fiona M. McDonald

  DOI：10.1016/s0960-894x(02)00481-x

  日期：2002.9

  Dihydroquinolines have been synthesized and have been shown to be potent n-NOS inhibitors. Selectivity versus e-NOS was increased to approximately 100-fold through appropriate substitution at the benzene ring. (C) 2002 Elsevier Science Ltd. All rights reserved.
• WO2007/41076
  申请人：——

  公开号：——

  公开（公告）日：——