R-3'-methoxywarfarin | 132295-01-3

• 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-3'-methoxywarfarin
• 英文别名: 4-hydroxy-3-[(1R)-1-(3-methoxyphenyl)-3-oxobutyl]chromen-2-one
• CAS: 132295-01-3
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: CJJPBGDXOLJMQU-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 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：

  4-羟基香豆素 、 4-(3-methoxyphenyl)but-3-en-2-one 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64%的产率得到R-3'-methoxywarfarin
  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

• Organocatalytic Enantioselective Michael Addition of 4-Hydroxycoumarin to α,β-Unsaturated Ketones: A Simple Synthesis of Warfarin
  作者：Zhenhua Dong、Lijia Wang、Xiaohong Chen、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1002/ejoc.200900831

  日期：2009.10

  secondary amine amide catalysts were developed for the asymmetric Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones. A series of important biologically and pharmaceutically active compounds were obtained in excellent yields (up to 99 %) with high enantioselectivities (up to 89 % ee) under mild conditions. In addition, enantiopure product could be obtained by a single recrystallization

  开发了一种 C2 对称仲胺酰胺催化剂，用于 4-羟基香豆素与 α,β-不饱和酮的不对称迈克尔加成。在温和的条件下，以优异的收率（高达 99%）和高对映选择性（高达 89% ee）获得了一系列重要的生物和药物活性化合物。此外，单次重结晶可以得到对映体纯的产物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 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.