N-hydroxy-N-methyl-α-2-propenylbenzenemethanamine | 113999-24-9

• 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-hydroxy-N-methyl-α-2-propenylbenzenemethanamine
• 英文别名: N-methyl-N-(1-phenyl-3-butenyl)hydroxylamine；N-methyl-N-(1-phenylbut-3-enyl)hydroxylamine
• CAS: 113999-24-9
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: SPDUHWKINAIYAN-UHFFFAOYSA-N

物化性质

• 沸点：
  283.3±29.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-N-methyl-α-2-propenylbenzenemethanamine 在 一氯化碘 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 trans-2-methyl-3-phenyl-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：

  N-甲基-C-苯基硝酮 、 氯丙烯镁 以 四氢呋喃 为溶剂， 反应 1.0h， 以94%的产率得到N-hydroxy-N-methyl-α-2-propenylbenzenemethanamine
  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

• Thermal and trimethylsilyl triflate catalyzed additions of allylsilanes to nitrones
  作者：Peter G. M. Wuts、Yong Woon Jung

  DOI：10.1021/jo00244a021

  日期：1988.4
• Organometallic reaction in aqueous media. A samarium induced, efficient, synthesis of homoallyl hydroxylamines and hydrazides
  作者：Dhrubojyoti D Laskar、Dipak Prajapati、Jagir S Sandhu

  DOI：10.1016/s0040-4039(01)01637-9

  日期：2001.10

  Samarium can be used directly for the allylation of aldonitrones and hydrazones in aqueous media in the presence of Bu4NBr. (C) 2001 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：——