(Z)-N-(2-dimethyl-t-butylsilyloxyethylidene)benzylamine N-oxide | 105623-21-0

• 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: (Z)-N-(2-dimethyl-t-butylsilyloxyethylidene)benzylamine N-oxide
• 英文别名: N-benzyl-2-[tert-butyl(dimethyl)silyl]oxyethanimine oxide
• CAS: 105623-21-0
• 化学式: C₁₅H₂₅NO₂Si
• 分子量: 279.454
• InChiKey: LTAQVORVWIYHQX-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-(2-dimethyl-t-butylsilyloxyethylidene)benzylamine N-oxide 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (3S,5R)-2-Benzyl-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-iodomethyl-isoxazolidine
  参考文献：
  名称：

  Trimethylsilyl triflate promoted addition of allyltributylstannane to aldonitrones; one-pot synthesis of 5-iodomethylisoxazolidines

  摘要：

  The trimethylsilyl triflate promoted allylation of nitrones with allyltributylstannane affords O-silylated hydroxylamines in high yield; when the crude reaction mixture is quenched with N-iodosuccinimide, 5-iodomethylisoxazolidines are formed in excellent yields. The overall one-pot two-step process represents a valuable improvement in terms of time, cost and overall yield with respect to the previously reported three stage procedure involving nitrone allylation, hydroxylamine O-silylation, and iodocyclisation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10862-0
• 作为产物：
  描述：

  叔丁基二甲基烯丙基硅醚 在 二甲基硫 、 臭氧 作用下， 以 乙醚 为溶剂， 反应 3.5h， 生成 (Z)-N-(2-dimethyl-t-butylsilyloxyethylidene)benzylamine N-oxide
  参考文献：
  名称：

  Fray, M. Jonathan; Jones, Richard H.; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2753 - 2762

  摘要：

  DOI：

文献信息

• FRAY, M. J.;JONES, R. H.;THOMAS, E. J., J. CHEM. SOC. PERKIN TRANS., 1985, N 12, 2753-2761
  作者：FRAY, M. J.、JONES, R. H.、THOMAS, E. J.

  DOI：——

  日期：——
• Fray, M. Jonathan; Jones, Richard H.; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2753 - 2762
  作者：Fray, M. Jonathan、Jones, Richard H.、Thomas, Eric J.

  DOI：——

  日期：——
• Trimethylsilyl triflate promoted addition of allyltributylstannane to aldonitrones; one-pot synthesis of 5-iodomethylisoxazolidines
  作者：Massimo Gianotti、Marco Lombardo、Claudio Trombini

  DOI：10.1016/s0040-4039(97)10862-0

  日期：1998.3

  The trimethylsilyl triflate promoted allylation of nitrones with allyltributylstannane affords O-silylated hydroxylamines in high yield; when the crude reaction mixture is quenched with N-iodosuccinimide, 5-iodomethylisoxazolidines are formed in excellent yields. The overall one-pot two-step process represents a valuable improvement in terms of time, cost and overall yield with respect to the previously reported three stage procedure involving nitrone allylation, hydroxylamine O-silylation, and iodocyclisation. (C) 1998 Elsevier Science Ltd. All rights reserved.