(2S,3R)-dimethyl 2-nitro-3-phenylcyclopropane-1,1-dicarboxylate | 910541-65-0

• 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: (2S,3R)-dimethyl 2-nitro-3-phenylcyclopropane-1,1-dicarboxylate
• 英文别名: dimethyl (2S,3R)-2-nitro-3-phenylcyclopropane-1,1-dicarboxylate
• CAS: 910541-65-0
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: IYKQWMXDSAGDGX-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl 2-chloro-2-((S)-2-nitro-1-phenylethyl)malonate 在 六甲基磷酰三胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 24.0h， 生成 (2S,3R)-dimethyl 2-nitro-3-phenylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  溴代丙二酸酯向α，β-不饱和硝基烯烃的有机催化共轭加成反应对硝基环丙烷的高度对映选择性

  摘要：

  硝基环丙烷的高度对映选择性合成是通过将溴代丙二酸二甲酯向硝基烯烃的有机催化共轭加成反应以及随后的分子内环丙烷化而实现的。发现6'-脱甲基奎宁是有效的催化剂。对于各种芳基或杂芳基硝基乙烯，获得了优异的对映选择性，非对映选择性和良好的收率。

  DOI：

  10.1021/ol900227j

文献信息

• Enantioselective synthesis of nitrocyclopropanes via conjugate addition of bromomalonate to nitroalkenes catalyzed by Ni(II) complexes
  作者：Hyun Joo Lee、Sun Mi Kim、Dae Young Kim

  DOI：10.1016/j.tetlet.2012.04.072

  日期：2012.7

  A novel one-pot methodology for the catalytic enantioselective synthesis of highly functionalized nitrocyclopropanes promoted by chiral nickel complexes is developed. The treatment of bromomalonates with nitroalkenes under the mild reaction conditions afforded the corresponding Michael adducts which cyclizes to controlled reaction conditions with excellent diasteroselectivities (>99 de) and enantioselectivities

  开发了一种新颖的一锅法，用于催化由手性镍配合物促进的高度官能化的硝基环丙烷的催化对映选择性合成。在温和的反应条件下用硝基烯烃处理溴代丙二酸酯，得到相应的迈克尔加合物，其以优异的非对映选择性（> 99 de）和对映选择性（高达99％ee）环化至受控的反应条件。
• Stereoselective synthesis of functionalised cyclopropanes from nitroalkenes via an organocatalysed Michael-initiated ring-closure approach
  作者：Alessio Russo、Alessandra Lattanzi

  DOI：10.1016/j.tetasy.2010.04.005

  日期：2010.5

  Synthetically useful nitrocyclopropanes are easily obtained via Michael addition of dimethyl bromomalonate to nitrostyrenes promoted by commercially available (S)-alpha,alpha-di-beta-naphthlyl-2-pyrrolidinemethanol as the catalyst, followed by DABCO-mediated intramolecular nucleophilic substitution. The functionalised nitrocyclopropanes are obtained in good yield, excellent diastereoselectivity and up to 49% ee. (C) 2010 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Synthesis of Nitrocyclopropanes via Organocatalytic Conjugate Addition of Bromomalonate to α,β-Unsaturated Nitroalkenes
  作者：Yi-ning Xuan、Shao-zhen Nie、Li-ting Dong、Jun-min Zhang、Ming Yan

  DOI：10.1021/ol900227j

  日期：2009.4.2

  Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6′-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for a variety of aryl or heteroaryl nitroethylenes

  硝基环丙烷的高度对映选择性合成是通过将溴代丙二酸二甲酯向硝基烯烃的有机催化共轭加成反应以及随后的分子内环丙烷化而实现的。发现6'-脱甲基奎宁是有效的催化剂。对于各种芳基或杂芳基硝基乙烯，获得了优异的对映选择性，非对映选择性和良好的收率。