(2S,3S)-ethyl-3-(tert-butoxycarbonylamino)-2-methyl-2-nitro-3-phenylpropanoate | 1088705-66-1

• 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: (2S,3S)-ethyl-3-(tert-butoxycarbonylamino)-2-methyl-2-nitro-3-phenylpropanoate
• 英文别名: ethyl (2S,3S)-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-nitro-3-phenylpropanoate
• CAS: 1088705-66-1
• 化学式: C₁₇H₂₄N₂O₆
• 分子量: 352.387
• InChiKey: XAPOLQOBPYBIBC-GUYCJALGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  氨基甲酸叔丁酯 在 甲酸 、 C₂₆H₂₈N₅O⁽¹⁺⁾*Cl^(1-) 、 potassium carbonate 、 sodium chloride 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 45.0h， 生成 (2S,3S)-ethyl-3-(tert-butoxycarbonylamino)-2-methyl-2-nitro-3-phenylpropanoate 、 (2R,3R)-ethyl-3-(tert-butoxycarbonylamino)-2-methyl-2-nitro-3-phenylpropanoate
  参考文献：
  名称：

  通过α-取代的硝基乙酸酯的催化不对称氮杂-亨利反应 构建手性季碳中心†

  摘要：

  Cinchona季铵盐催化N - Boc Aldimines 2和2-硝基丙酸乙酯3在甲苯-饱和盐水（10：1）混合溶剂中的催化对映选择性aza-Henry反应，形成一个新的季碳中心。在温和条件下成功获得了高收率（高达90％），出色的对映选择性（高达99％ee）和非对映选择性比（高达22：1）。

  DOI：

  10.1039/c4ra01390e

文献信息

• Enantioselective catalytic addition of nitroesters to N-carboalkyloxy imines: a route to quaternary stereocenters
  作者：Alessandra Puglisi、Laura Raimondi、Maurizio Benaglia、Martina Bonsignore、Sergio Rossi

  DOI：10.1016/j.tetlet.2009.05.036

  日期：2009.7

  A readily available, low cost bifunctional organic catalyst promoted the addition of nitroesters to imines; in the reaction between 2-nitropropionates and N-Boc protected aldehyde-imines the product bearing a new quaternary stereocenter was obtained in up to 81% ee. The positively charged catalyst was postulated to control the attack of the enolic form of nitroester to imine through a hydrogen bonding

  一种易于获得的低成本双功能有机催化剂促进了亚硝酸酯类向亚胺中的添加。在2-硝基丙酸酯与N - Boc保护的醛-亚胺之间的反应中，获得具有新的季立体中心的产物，其收率高达81％ee。假定带正电荷的催化剂通过氢键网络控制硝基酯的烯醇形式对亚胺的攻击。
• Discovery of Bifunctional Thiourea/Secondary-Amine Organocatalysts for the Highly Stereoselective Nitro-Mannich Reaction of α-Substituted Nitroacetates
  作者：Bo Han、Qing-Ping Liu、Rui Li、Xu Tian、Xiao-Feng Xiong、Jin-Gen Deng、Ying-Chun Chen

  DOI：10.1002/chem.200801170

  日期：2008.9.19
• Asymmetric aza-Henry reaction with α-substituted nitroacetates catalyzed by a bifunctional thiourea-guanidine catalyst
  作者：Bo Han、Wei Huang、Zhen Rui Xu、Xiao Ping Dong

  DOI：10.1016/j.cclet.2011.01.038

  日期：2011.8

  The asymmetric aza-Henry reaction of a-substituted nitroacetates and N-Boc imines was achieved with a new-type thiourea-guanidine bifunctional organocatalyst. The novel transformations exhibited high diastereoselectivities, and the adducts bearing adjacent quaternary and tertiary chiral centers were generally obtained in moderate to good enantioselectivities (up to 88% ee). (C) 2011 Wei Huang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates
  作者：Minghua Li、Nan Ji、Ting Lan、Wei He、Rui Liu

  DOI：10.1039/c4ra01390e

  日期：——

  The catalytic enantioselective aza-Henry reaction of N-Boc aldimines 2 and 2-nitropropionic acid ethyl ester 3 in the mixed solvents of toluene–saturated brine (10 : 1) was catalyzed by cinchona quaternary ammonium salts to form a new quaternary carbon center. High yields (up to 90%), and excellent enantioselectivities (up to 99% ee) and diastereoselectivity ratio (up to 22 : 1) were successfully obtained

  Cinchona季铵盐催化N - Boc Aldimines 2和2-硝基丙酸乙酯3在甲苯-饱和盐水（10：1）混合溶剂中的催化对映选择性aza-Henry反应，形成一个新的季碳中心。在温和条件下成功获得了高收率（高达90％），出色的对映选择性（高达99％ee）和非对映选择性比（高达22：1）。