6-chloro-4-hydroxy-3-[(1R)-1-(2-methoxyphenyl)-3-oxobutyl]chromen-2-one | 1262056-68-7

• 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: 6-chloro-4-hydroxy-3-[(1R)-1-(2-methoxyphenyl)-3-oxobutyl]chromen-2-one
• CAS: 1262056-68-7
• 化学式: C₂₀H₁₇ClO₅
• 分子量: 372.805
• InChiKey: NJRDAHPXKTYUPM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氯-4-羟基香豆素 、 2-methoxybenzalacetone 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69%的产率得到6-chloro-4-hydroxy-3-[(1R)-1-(2-methoxyphenyl)-3-oxobutyl]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

• Highly enantioselective synthesis of warfarin and its analogs by means of cooperative LiClO4/DPEN-catalyzed Michael reaction: enantioselectivity enhancement and mechanism
  作者：Hua-Meng Yang、Li Li、Ke-Zhi Jiang、Jian-Xiong Jiang、Guo-Qiao Lai、Li-Wen Xu

  DOI：10.1016/j.tet.2010.10.032

  日期：2010.12

  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.