dibenzyl 2-[(1S,2R)-2-(3,5-dinitrobenzamido)cyclohexyl]malonate | 1283635-91-5

• 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: dibenzyl 2-[(1S,2R)-2-(3,5-dinitrobenzamido)cyclohexyl]malonate
• 英文别名: dibenzyl 2-[(1S,2R)-2-[(3,5-dinitrobenzoyl)amino]cyclohexyl]propanedioate
• CAS: 1283635-91-5
• 化学式: C₃₀H₂₉N₃O₉
• 分子量: 575.575
• InChiKey: SHCFVSJEZNZMTK-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 、 二苄基马来酸酯 在 lanthanum(III) isopropoxide 、 ytterbium(III) trifluoroacetate 、 N,N'-bis(3-methoxysalicylidene)(binaphthyl)-1,4-diamine 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以97%的产率得到dibenzyl 2-[(1S,2R)-2-(3,5-dinitrobenzamido)cyclohexyl]malonate
  参考文献：
  名称：

  Catalytic Asymmetric Ring-Opening ofmeso-Aziridines with Malonates under Heterodinuclear Rare Earth Metal Schiff Base Catalysis

  摘要：

  Catalytic asymmetric ring-opening of meso-aziridines with malonates is described. The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction. A 1:1:1 mixture of a heterobimetallic La(O-iPr)(3)/Yb(OTf)(3)/Schiff base la (0.25-10 mol %) efficiently promoted the reaction of five-, six-, and seven-membered ring cyclic meso-aziridines as well as acyclic meso-aziridines with dimethyl, diethyl, and dibenzyl malonates, giving chiral cyclic and acyclic gamma-amino esters in 99-63% yield and > 99.5-97% ee.

  DOI：

  10.1021/ja201492x

文献信息

• Catalytic Asymmetric Ring-Opening of<i>meso-</i>Aziridines with Malonates under Heterodinuclear Rare Earth Metal Schiff Base Catalysis
  作者：Yingjie Xu、Luqing Lin、Motomu Kanai、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja201492x

  日期：2011.4.20

  Catalytic asymmetric ring-opening of meso-aziridines with malonates is described. The combined use of two rare earth metal sources with different properties promoted the desired ring-opening reaction. A 1:1:1 mixture of a heterobimetallic La(O-iPr)(3)/Yb(OTf)(3)/Schiff base la (0.25-10 mol %) efficiently promoted the reaction of five-, six-, and seven-membered ring cyclic meso-aziridines as well as acyclic meso-aziridines with dimethyl, diethyl, and dibenzyl malonates, giving chiral cyclic and acyclic gamma-amino esters in 99-63% yield and > 99.5-97% ee.