(Z)-3-Acetylamino-but-2-enoic acid benzyl ester | 505092-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-Acetylamino-but-2-enoic acid benzyl ester
• 英文别名: Benzyl 3-acetamidobut-2-enoate；benzyl 3-acetamidobut-2-enoate
• CAS: 505092-89-7
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: NYVAYJMGDWOMQI-UHFFFAOYSA-N

物化性质

• 熔点：
  50-53 °C
• 沸点：
  414.4±37.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-Acetylamino-but-2-enoic acid benzyl ester 在 [Rh(COD)(R,R)-bis(diphenylphosphino)-1,3-(Ph₂)propane]BF₄ 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 生成 (3S)-3-乙酰氨基丁酸苄酯 、 (R)-3-Acetylamino-butyric acid benzyl ester
  参考文献：
  名称：

  Economic preparation of 1,3-diphenyl-1,3-bis(diphenylphosphino)propane: a versatile chiral diphosphine ligand for enantioselective hydrogenations

  摘要：

  The enantioselective hydrogenation of 1,3-diarylpropane-1,3-diones with chiral Ru(II)-diphosphine catalyst has been studied. In a first approach it was found, that Tol-BINAP together with Ru(COD)methallyl(2) formed the most selective catalyst. One of the C-2-symmetric enantiopure 1,3-diols obtained in turn was transformed via its 1,3-di-O-mesylate into 1,3-bisdiarylphosphines. One of them, 1,3-diphenyl-1,3-bis(diphenylphosphino)propane, could be advantageously utilized as a ligand for the efficient enantioselective Ru-catalyzed hydrogenation of its own 1,3-diketone precursor. Thus, the condition for a 'cross self-breeding' catalytic system is fulfilled. A further reduction of the preparation costs could be achived by application of RuCl3.H2O instead of other more expensive precatalyst precursors without compromosing the enantioselectivity. The ligand was used in the Rh(I)-catalyzed asymmetric hydrogenation of model substrates and beta-amino acid precursors where up to 97% ee could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00595-0

文献信息

• Novel bisphosphane catalysts
  申请人：Holz Jens

  公开号：US20070197799A1

  公开（公告）日：2007-08-23

  In the present application protection is sought for compounds of the general formula (I) as ligands for reactions catalysed by transition metals. The preparation thereof and use thereof, in particular for the preparation of β-amino acids, is also discussed.
• Economic preparation of 1,3-diphenyl-1,3-bis(diphenylphosphino)propane: a versatile chiral diphosphine ligand for enantioselective hydrogenations
  作者：Natalia V. Dubrovina、Vitali I. Tararov、Axel Monsees、Renat Kadyrov、Christine Fischer、Armin Börner

  DOI：10.1016/s0957-4166(03)00595-0

  日期：2003.9

  The enantioselective hydrogenation of 1,3-diarylpropane-1,3-diones with chiral Ru(II)-diphosphine catalyst has been studied. In a first approach it was found, that Tol-BINAP together with Ru(COD)methallyl(2) formed the most selective catalyst. One of the C-2-symmetric enantiopure 1,3-diols obtained in turn was transformed via its 1,3-di-O-mesylate into 1,3-bisdiarylphosphines. One of them, 1,3-diphenyl-1,3-bis(diphenylphosphino)propane, could be advantageously utilized as a ligand for the efficient enantioselective Ru-catalyzed hydrogenation of its own 1,3-diketone precursor. Thus, the condition for a 'cross self-breeding' catalytic system is fulfilled. A further reduction of the preparation costs could be achived by application of RuCl3.H2O instead of other more expensive precatalyst precursors without compromosing the enantioselectivity. The ligand was used in the Rh(I)-catalyzed asymmetric hydrogenation of model substrates and beta-amino acid precursors where up to 97% ee could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.