ethyl (Z)-3-(4-chlorophenylamino)-3-(4-methoxyphenyl)acrylate | 1621603-72-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (Z)-3-(4-chlorophenylamino)-3-(4-methoxyphenyl)acrylate
• 英文别名: (Z)-ethyl 3-((4-chlorophenyl)amino)-3-(4-methoxyphenyl)acrylate
• CAS: 1621603-72-2
• 化学式: C₁₈H₁₈ClNO₃
• 分子量: 331.799
• InChiKey: XVESKDCFZDECGT-ATVHPVEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-3-(4-chlorophenylamino)-3-(4-methoxyphenyl)acrylate 在 dicobalt octacarbonyl 、 一氧化碳 、 氢气 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 120.0 ℃ 、3.1 MPa 条件下， 反应 36.0h， 以43%的产率得到
  参考文献：
  名称：

  Cobalt-catalyzed hydrogenation of β-enamino esters using an internal mixture of bidentate and monodentate ligands

  摘要：

  Different beta-amino esters have been obtained in good yields by means of octacarbonyldicobalt-catalyzed hydrogenation of beta-enamine esters in the presence of mixture of a bidentate phosphine chiral (R-BINAP) and a monodentate phosphine achiral (PPh3). Likewise, a non-symmetric Co/BINAP/PPh3 complex was isolated. This new compound was used in the hydrogenation reaction under different conditions and the results suggest that this heterocombination could be responsible for improving enantiomeric excess in the reduction products. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.06.028
• 作为产物：
  描述：

  对氯苯胺 、 3-(4-甲氧苯基)-3-氧代丙酸乙酯 在 cobalt(II) chloride 作用下， 反应 12.0h， 以83%的产率得到ethyl (Z)-3-(4-chlorophenylamino)-3-(4-methoxyphenyl)acrylate
  参考文献：
  名称：

  Cobalt-catalyzed hydrogenation of β-enamino esters using an internal mixture of bidentate and monodentate ligands

  摘要：

  Different beta-amino esters have been obtained in good yields by means of octacarbonyldicobalt-catalyzed hydrogenation of beta-enamine esters in the presence of mixture of a bidentate phosphine chiral (R-BINAP) and a monodentate phosphine achiral (PPh3). Likewise, a non-symmetric Co/BINAP/PPh3 complex was isolated. This new compound was used in the hydrogenation reaction under different conditions and the results suggest that this heterocombination could be responsible for improving enantiomeric excess in the reduction products. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.06.028

文献信息

• Asymmetric transfer hydrogenations of β-N-substituted enamino esters with ammonia borane
  作者：Weiwei Zhao、Xiangqing Feng、Jing Yang、Haifeng Du

  DOI：10.1016/j.tetlet.2019.03.060

  日期：2019.4

  β-enamino esters is one of the most efficient approaches for their synthesis. Ammonia borane with low molecular weight, high hydrogen capacity, and good stability, is an ideal hydrogen source for the transfer hydrogenation. However, only a few successful examples have been reported for the asymmetric reduction with ammonia borane. In this work, an asymmetric metal-free transfer hydrogenation of β-N-substituted

  旋光性β-氨基酸及其衍生物是合成和药物化学中非常有用的组成部分。β-烯氨基酯的催化不对称还原是最有效的合成方法之一。低分子量，高氢气容量和良好稳定性的氨硼烷是转移加氢的理想氢源。但是，只有少数成功的例子报道了用氨硼烷进行不对称还原。在这项工作中，β-不对称无金属转移氢化Ñ取代与ammoinia硼烷烯酯成功通过使用路易斯受挫对桥墩的硼烷和（实现小号） -叔-丁基亚磺酰胺作为手性催化剂。以51–90％的产率获得了多种β-氨基酸衍生物，ee高达91％。