(2R,3R)-2-((S)-2-nitro-1-phenylethyl)-1,3-diphenylpentan-1-one | 1334671-25-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2R,3R)-2-((S)-2-nitro-1-phenylethyl)-1,3-diphenylpentan-1-one
• 英文别名: (2R,3R)-2-[(1S)-2-nitro-1-phenylethyl]-1,3-diphenylpentan-1-one
• CAS: 1334671-25-8
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: WOKRPINHVPVVMC-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反式-查耳酮 在 bis(acetylacetonate)nickel(II) 、 (1S,2R,4R)-7,7-dimethyl-1-morpholin-4-yl-bicyclo[2.2.1]heptan-2-ol 作用下， 以 正己烷 为溶剂， 反应 2.25h， 生成 (2R,3R)-2-((S)-2-nitro-1-phenylethyl)-1,3-diphenylpentan-1-one 、 (2S,3S)-2-((R)-2-nitro-1-phenylethyl)-1,3-diphenylpentan-1-one
  参考文献：
  名称：

  Highly enantioselective tandem double Michael reactions catalyzed by Ni(acac)2/(+)-MINBOL complex

  摘要：

  An in situ prepared complex of chiral ligand (+)-MINBOL 1 and Ni(acac)(2) (12.5 mol % and 0.5 mol % respectively) can efficiently catalyze enantioselective tandem double Michael reactions. In this reaction, aryl or alkyl nitroalkenes were employed as electrophiles. The corresponding tandem adducts were obtained in good yields and with high enantioselectivities (up to 97% ee). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.10.012

文献信息

• Highly Diastereo- and Enantioselective Tandem Reaction toward Functionalized Pyrrolidines with Multiple Stereocenters
  作者：Shengmei Guo、Yinjun Xie、Xinquan Hu、Hanmin Huang

  DOI：10.1021/ol2023196

  日期：2011.10.21

  An efficient asymmetric tandem dual Michael reaction that constructs three contiguous stereocenters in acyclic open-chain systems with very high enantioselectivity and diastereoselectivity has been developed. This protocol provides a reliable and rapid approach for synthesis of chiral pyrrolidines with multiple stereocenters.

  已经开发了一种有效的不对称串联对偶迈克尔反应，该反应在对映选择性和非对映选择性非常高的无环开链系统中构建了三个连续的立体中心。该方案为合成具有多个立体中心的手性吡咯烷提供了一种可靠而快速的方法。
• Copper-catalyzed asymmetric tandem double Michael reactions of diethylzinc to α,β-unsaturated ketones followed by trapping with nitroolefins
  作者：Qiang Wang、Shuang Li、Chuan-Jin Hou、Ting-Ting Chu、Xiang-Ping Hu

  DOI：10.1016/j.tet.2019.06.032

  日期：2019.7

  A copper catalyzed asymmetric tandem double Michael addition of diethylzinc to α,β-unsaturated ketones followed by trapping with nitroolefins has been developed using chiral P,N-ligands. The tandem products were obtained in good yields and excellent enantioselectivities with three contiguous stereocenters.

  使用手性P，N-配体已经开发了铜催化的不对称串联双迈克尔将二乙基锌加成到α，β-不饱和酮上，然后用硝基烯烃捕获的方法。串联产物以三个连续的立体中心以良好的产率和优异的对映选择性获得。