(Z,2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-imine oxide | 160836-04-4

• 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: (Z,2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-imine oxide
• CAS: 160836-04-4
• 化学式: C₃₂H₅₁NO₄Si₂
• 分子量: 569.932
• InChiKey: WCYHGSRTJJTISA-RJULVASWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z,2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-imine oxide 以 苯 为溶剂， 反应 12.0h， 生成 (4R,6S,7S)-2-Benzyl-4-benzyloxymethyl-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxa-2-aza-bicyclo[3.2.0]heptane
  参考文献：
  名称：

  Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

  摘要：

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

  DOI：

  10.1021/jo00095a008
• 作为产物：
  描述：

  (Z)-(2S,3S)-6-Benzyloxy-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-hex-4-en-1-ol 在 Swern oxidation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (Z,2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-phenylmethoxyhex-4-en-1-imine oxide
  参考文献：
  名称：

  Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

  摘要：

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

  DOI：

  10.1021/jo00095a008