(2R,3S)-methyl 2-methyl-3-(p-methoxyphenylamino)-3-(p-chloro-phenyl)propanoate | 1412838-51-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3S)-methyl 2-methyl-3-(p-methoxyphenylamino)-3-(p-chloro-phenyl)propanoate
• 英文别名: methyl (2R,3S)-2-methyl-3-(p-methoxyphenylamino)-3-(p-chlorophenyl)propanoate；methyl (2R,3S)-3-(4-chlorophenyl)-3-(4-methoxyanilino)-2-methylpropanoate
• CAS: 1412838-51-7
• 化学式: C₁₈H₂₀ClNO₃
• 分子量: 333.815
• InChiKey: HDTLYZFKAJINKG-PXAZEXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 (5S,2'R,3'S)-5-isopropyl-3-phenyl-1-[2'-methyl-3'-(p-methoxyphenylamino)-3'-(p-chlorophenyl)propionyl]hydantoin 在 4-二甲氨基吡啶 作用下， 反应 8.0h， 以85%的产率得到(2R,3S)-methyl 2-methyl-3-(p-methoxyphenylamino)-3-(p-chloro-phenyl)propanoate
  参考文献：
  名称：

  Asymmetric and diastereoselective Mannich reactions using hydantoin as a chiral auxiliary

  摘要：

  The Mannich reaction of titanium enolates of a chiral hydantoin with various aldimines smoothly occurred in good yields and with high anti-diastereoselectivity. The Mannich adducts can be readily cleaved by alcoholysis to afford several beta-amino ester derivatives in good yields and in almost enantiomerically pure form. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.006

文献信息

• Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary
  作者：Liang Zhu、Cuifen Lu、Zuxing Chen、Guichun Yang、Yan Li、Junqi Nie

  DOI：10.1016/j.tetasy.2014.11.008

  日期：2015.1

  Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values. (C) 2014 Elsevier Ltd. All rights reserved.
• Asymmetric and diastereoselective Mannich reactions using hydantoin as a chiral auxiliary
  作者：Xuan-Ran Li、Cui-Fen Lu、Zu-Xing Chen、Yan Li、Gui-Chun Yang

  DOI：10.1016/j.tetasy.2012.09.006

  日期：2012.10

  The Mannich reaction of titanium enolates of a chiral hydantoin with various aldimines smoothly occurred in good yields and with high anti-diastereoselectivity. The Mannich adducts can be readily cleaved by alcoholysis to afford several beta-amino ester derivatives in good yields and in almost enantiomerically pure form. (C) 2012 Elsevier Ltd. All rights reserved.