(R)-6-chloro-4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one | 1262056-67-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (R)-6-chloro-4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
• 英文别名: 6-chloro-4-hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]chromen-2-one
• CAS: 1262056-67-6
• 化学式: C₁₉H₁₅ClO₄
• 分子量: 342.779
• InChiKey: ICOBWHCNJIGPAM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-氯-4-羟基香豆素 、 苄叉丙酮 在 lithium perchlorate trihydrate 、 (1R,2R)-1,2-二苯基乙二胺 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以61%的产率得到(R)-6-chloro-4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
  参考文献：
  名称：

  Highly enantioselective synthesis of warfarin and its analogs by means of cooperative LiClO4/DPEN-catalyzed Michael reaction: enantioselectivity enhancement and mechanism

  摘要：

  The highly enantioselective synthesis of warfarin and its analogs was reported in this manuscript And a cooperative catalysis was observed in asymmetric primary amine-catalyzed Michael reaction for the enantioselective synthesis of warfarin and its analogs, which led to the finding of several cooperative catalyst systems combined with Lewis acid and primary amine, such as LiClO4/DPEN. In this Michael reaction of 4-hydrocoumarin, the cooperative catalyst system (LiClO4/DPEN) resulted in higher levels of stereoselectivity (up to 94%ee). Additionally, the mechanism of the enantioselectivity enhancement in the cooperative catalytic Michael reaction has been investigated by using of ESI-MS and the study of nonlinear effect. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.032

文献信息

• First aromatic amine organocatalysed activation of α,β-unsaturated ketones
  作者：Isaac G. Sonsona、Eugenia Marqués-López、M. Concepción Gimeno、Raquel P. Herrera

  DOI：10.1039/c9nj02392e

  日期：——

  This work provides an unprecedented example of a chiral aromatic amine used to activate α,β-unsaturated ketones in asymmetric aminocatalysis. Chiral aromatic diamine VII has been efficiently employed, as a proof of concept, in the Michael addition reaction between benzylideneacetones (1a–f) and coumarins (2a–d). The reaction gives rise to warfarin derivatives 3 with promising results using this family

  这项工作提供了一个空前的手性芳香胺实例，用于在不对称氨基催化中活化α，β-不饱和酮。作为概念证明，手性芳族二胺VII已有效地用于亚苄基丙酮（1a–f）和香豆素（2a–d）之间的迈克尔加成反应。该反应首次使用该族催化剂产生了具有可喜结果的华法林衍生物3。进行的其他研究支持了手性催化剂VII活化的双功能模式以及催化剂VII与亚苄基丙酮1之间相互作用的共价性质。
• Chiral Primary Amino Amide Alcohol Organocatalyst for the Asymmetric Michael Addition of 4-Hydroxycoumarin with α,β-Unsaturated Ketones
  作者：Hiroto Nakano、Jun Kumagai、Yoshihito Kohari、Chigusa Seki、Koji Uwai、Yuko Okuyama、Eunsang Kwon

  DOI：10.3987/com-14-s(k)83

  日期：——

  Chiral primary amino amide organocatalysts were designed and synthesized as new organocatalysts for the enantioselective Michael addition of 4-hydroxycoumarin with alpha,beta-unsaturated ketones to produce chiral warfarin (up to 56% ee with up to 92% yield).