tert-butyl (2R)-2-[(S)-[(2-methylpropan-2-yl)oxycarbonylamino]-phenylmethyl]-2-nitrobutanoate | 1044200-66-9

• 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: tert-butyl (2R)-2-[(S)-[(2-methylpropan-2-yl)oxycarbonylamino]-phenylmethyl]-2-nitrobutanoate
• CAS: 1044200-66-9
• 化学式: C₂₀H₃₀N₂O₆
• 分子量: 394.468
• InChiKey: WUEASKYVDTZHCT-MGPUTAFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  benzaldehyde N-boc imine 、 tert-butyl α-ethylnitroacetate 在 C₃₄H₃₄ClNO 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (2RS,3SR)-tert-butyl 3-(tert-butoxycarbonylamino)-2-ethyl-2-nitro-3-phenylpropanoate 、 tert-butyl (2R)-2-[(S)-[(2-methylpropan-2-yl)oxycarbonylamino]-phenylmethyl]-2-nitrobutanoate
  参考文献：
  名称：

  Performance of C1-symmetric chiral ammonium betaines as catalysts for the enantioselective Mannich-type reaction of α-nitrocarboxylates

  摘要：

  The catalytic performance of C-1-symmetric chiral ammonium betaines in the enantioselective direct Mannich-type reaction of alpha-nitrocarboxylates with N-Boc imines has been investigated. The most effective catalyst structure has been identified; this provides a reliable synthetic route to a variety of enantiomerically enriched alpha-tetrasubstituted alpha,beta-diamino acid derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.006

文献信息

• Chiral Ammonium Betaines: A Bifunctional Organic Base Catalyst for Asymmetric Mannich-Type Reaction of α-Nitrocarboxylates
  作者：Daisuke Uraguchi、Kyohei Koshimoto、Takashi Ooi

  DOI：10.1021/ja8041004

  日期：2008.8.1

  A chiral ammonium betaine, an intramolecular ion-pairing quaternary ammonium aryloxide 3, has been designed and its vast potential as an enantioselective organic base catalyst has been successfully demonstrated in the highly enantioselective direct Mannich-type reaction of alpha-substituted alpha-nitrocarboxylates 2 with various N-Boc imines 1. The present study provides a conceptually new approach

  设计了一种手性铵甜菜碱，一种分子内离子对季铵芳氧化物 3，其作为对映选择性有机碱催化剂的巨大潜力已在 α 取代的 α-硝基羧酸盐 2 与各种 N-Boc 亚胺 1. 本研究为设计双功能手性季铵盐及其作为均相有机分子催化剂的用途提供了一种概念上的新方法。