N-[(trimethylsilyl)oxy]-N-(phenylmethyl)-2-methyl-5-hexen-3-amine | 133985-95-2

• 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: N-[(trimethylsilyl)oxy]-N-(phenylmethyl)-2-methyl-5-hexen-3-amine
• 英文别名: N-benzyl-2-methyl-N-trimethylsilyloxyhex-5-en-3-amine
• CAS: 133985-95-2
• 化学式: C₁₇H₂₉NOSi
• 分子量: 291.509
• InChiKey: UVTYYFAQKHEGJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(trimethylsilyl)oxy]-N-(phenylmethyl)-2-methyl-5-hexen-3-amine 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 trans-(2-phenylmethyl)-3-(α-methylethyl)-5-(iodomethyl)isoxazolidine 、 cis-(2-phenylmethyl)-3-(α-methylethyl)-5-(iodomethyl)isoxazolidine
  参考文献：
  名称：

  A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines

  摘要：

  N,N-Dialkyl-O-trialkylsilyl homoallylic hydroxylamines reacted with iodine, N-iodosuccinimide, or iodine chloride to give 3,5-disubstituted isoxazolidines in good yield. The relative configuration that was generated at C3 and C5 was controlled by the nature of the nitrogen substituent of the parent hydroxylamine: the presence of a primary alkyl group favored the formation of a cis-isoxazolidine, whereas the presence of a tert-butyl group favored the formation of a trans-isoxazolidine. The effects that the N- and O-substituents and the nature of the iodinating agent exerted on the stereoselectivity of the cyclization were examined. The synthesis of enantiomerically pure isoxazolidines from hydroxylamines carrying a chiral N-mannofuranosyl group is described.

  DOI：

  10.1021/jo00013a032
• 作为产物：
  描述：

  (Z)-N-(2-methylpropylidene)benzylamine N-oxide 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(trimethylsilyl)oxy]-N-(phenylmethyl)-2-methyl-5-hexen-3-amine
  参考文献：
  名称：

  A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines

  摘要：

  N,N-Dialkyl-O-trialkylsilyl homoallylic hydroxylamines reacted with iodine, N-iodosuccinimide, or iodine chloride to give 3,5-disubstituted isoxazolidines in good yield. The relative configuration that was generated at C3 and C5 was controlled by the nature of the nitrogen substituent of the parent hydroxylamine: the presence of a primary alkyl group favored the formation of a cis-isoxazolidine, whereas the presence of a tert-butyl group favored the formation of a trans-isoxazolidine. The effects that the N- and O-substituents and the nature of the iodinating agent exerted on the stereoselectivity of the cyclization were examined. The synthesis of enantiomerically pure isoxazolidines from hydroxylamines carrying a chiral N-mannofuranosyl group is described.

  DOI：

  10.1021/jo00013a032

文献信息

• 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.
• MANCINI, FABRIZIO;PIAZZA, MARIA GIULIA;TROMBINI, CLAUDIO, J. ORG. CHEM., 56,(1991) N3, C. 4246-4252
  作者：MANCINI, FABRIZIO、PIAZZA, MARIA GIULIA、TROMBINI, CLAUDIO

  DOI：——

  日期：——