(R)-2-(((S)-tert-butoxycarbonylamino)(4-chlorophenyl)methyl)-2-cyanocyclopentanone | 1023754-78-0

• 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: (R)-2-(((S)-tert-butoxycarbonylamino)(4-chlorophenyl)methyl)-2-cyanocyclopentanone
• 英文别名: tert-butyl N-[(S)-(4-chlorophenyl)-[(1R)-1-cyano-2-oxocyclopentyl]methyl]carbamate
• CAS: 1023754-78-0
• 化学式: C₁₈H₂₁ClN₂O₃
• 分子量: 348.829
• InChiKey: TXUJEUXCGVJJMK-MAUKXSAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氰基环戊酮 、 (E)-tert-butyl 4-chlorobenzylidenecarbamate 在 (S)-N-(2-hydroxyphenyl)-2-salicyloylaminoisovaleramide 、 Sc(OiPr)3 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-((tert-butoxycarbonylamino)(4-chlorophenyl)methyl)-2-cyanocyclopentanone 、 (R)-2-(((S)-tert-butoxycarbonylamino)(4-chlorophenyl)methyl)-2-cyanocyclopentanone 、 2-((tert-butoxycarbonylamino)(4-chlorophenyl)methyl)-2-cyanocyclopentanone
  参考文献：
  名称：

  Asymmetric Catalysis via Dynamic Substrate/Ligand/Rare Earth Metal Conglomerate

  摘要：

  A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of acyanoketones and N-Boc imines promoted by an amide ligand/Sc(OiPr)(3) catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction i components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.

  DOI：

  10.1021/ja800326d

文献信息

• Asymmetric Catalysis via Dynamic Substrate/Ligand/Rare Earth Metal Conglomerate
  作者：Akihiro Nojiri、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja800326d

  日期：2008.4.1

  A highly enantio- and diastereoselective catalytic asymmetric Mannich-type reaction of acyanoketones and N-Boc imines promoted by an amide ligand/Sc(OiPr)(3) catalyst is described. The similar reaction outcome is obtained with/without precomplexation of catalyst, suggesting that reaction i components in a non-ordered conglomerate mixture orchestrate to form an ordered transition state during the reaction. Spectroscopic data and Eyring plot are consistent with this assumption.