(3aR,7aR,1'S,2'S)-2-(2'-methoxycarbonyl-1'-trimethylsilylcycloprop-1'-yl)-1,3-dineopentylperhydro-1,3,2-λ5-benzodiazaphosphol-2-thione | 1109231-48-2

• 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: (3aR,7aR,1'S,2'S)-2-(2'-methoxycarbonyl-1'-trimethylsilylcycloprop-1'-yl)-1,3-dineopentylperhydro-1,3,2-λ5-benzodiazaphosphol-2-thione
• 英文别名: methyl (1S,2S)-2-[(3aR,7aR)-1,3-bis(2,2-dimethylpropyl)-2-sulfido-3a,4,5,6,7,7a-hexahydrobenzo[d][1,3,2]diazaphosphol-2-ium-2-yl]-2-trimethylsilylcyclopropane-1-carboxylate
• CAS: 1109231-48-2
• 化学式: C₂₄H₄₇N₂O₂PSSi
• 分子量: 486.775
• InChiKey: RIMWHUPORZTTOZ-UECWXEIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  33.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3aR,7aR)-2-[diazo(trimethylsilyl)methyl]-1,3-dineopentylperhydro-1,3,2-benzodiazaphosphole 、 丙烯酸甲酯（MA） 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以66%的产率得到(3aR,7aR,1'S,2'S)-2-(2'-methoxycarbonyl-1'-trimethylsilylcycloprop-1'-yl)-1,3-dineopentylperhydro-1,3,2-λ5-benzodiazaphosphol-2-thione
  参考文献：
  名称：

  Understanding the π-facial diastereoselectivity in the addition of chiral diaminophosphino(silyl)carbenes to activated olefins

  摘要：

  The synthesis of a new chiral diaminophosphino(silyl)carbene, based on the use of (R,R)-cyclotlexane-trans-1,2-diamine, is described. Its reaction with methyl acrylate afforded a cyclopropane derivative as a single diastereomer. The diastereoselectivity in the addition reactions between olefins and chiral carbenes derived from C-2-symmetric diamines has also been Studied by theoretical calculations, which establish that it has a steric origin; we report a rationale to predict the absolute configuration of the adducts. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.021