(2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]pent-4-en-1-imine oxide | 160835-99-4

• 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: (2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]pent-4-en-1-imine oxide
• CAS: 160835-99-4
• 化学式: C₂₄H₄₃NO₃Si₂
• 分子量: 449.781
• InChiKey: ZKKWWAZPYBILNO-YIIVROEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]pent-4-en-1-imine oxide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 反应 12.0h， 生成 [(1R,2S,3S,4R)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-cyclobutyl]-carbamic acid tert-butyl ester
  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：

  (2S,3S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-pent-4-en-1-ol 在 Swern oxidation 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3S)-N-benzyl-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]pent-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

文献信息

• Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines
  作者：Seiki Saito、Teruhiko Ishikawa、Toshio Moriwake

  DOI：10.1021/jo00095a008

  日期：1994.8

  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.