C-pentyl-N-methylnitrone | 133985-96-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: C-pentyl-N-methylnitrone
• 英文别名: N-methylhexan-1-imine oxide
• CAS: 133985-96-3
• 化学式: C₇H₁₅NO
• 分子量: 129.202
• InChiKey: QJGZVZWTNKXLED-FPLPWBNLSA-N

物化性质

• 沸点：
  267.2±7.0 °C(Predicted)
• 密度：
  0.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  C-pentyl-N-methylnitrone 在 N-碘代丁二酰亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 trans-2-methyl-3-pentyl-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-甲基羟胺 、 正己醛 在 盐酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 C-pentyl-N-methylnitrone
  参考文献：
  名称：

  Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate

  摘要：

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.

  DOI：

  10.1021/ol0347388

文献信息

• Reverse-Cope cyclisations of thiahydroxylamines derived from the addition of allylic thiols to nitrones: Syntheses of 1,3-thiazolidine-N-oxides and 1,5,2-oxathiazinanes
  作者：Michael P Coogan、Michael B Gravestock、David W Knight、Steven R Thornton

  DOI：10.1016/s0040-4039(97)10244-1

  日期：1997.12

  Allylthiols 7 react as nucleophiles with nitrones 8 to give intermediate thiahydroxylamines which undergo reverse-Cope cyclisations to provide 1,3-thiazolidine-N-oxides 9; in the case of derivatives of C-phenyl nitrone, thermolysis results in smooth Meisenheimer rearrangement leading to the 1,5,2-oxathiazinane 14.

  烯丙基硫醇7作为亲核试剂与硝酮8反应，生成中间体噻羟胺，将其进行反向Cope环化反应以提供1,3-噻唑烷-N-氧化物9；在C-苯基硝酮的衍生物的情况下，热分解导致平滑的Meisenheimer重排，从而导致1,5,2-氧杂噻嗪烷14。
• 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：——
• US5584919A
  申请人：——

  公开号：US5584919A

  公开（公告）日：1996-12-17
• Synthesis of Functionalized Sulfonamides via 1,3-Dipolar Cycloaddition of Pentafluorophenyl Vinylsulfonate
  作者：Stephen Caddick、Hannah D. Bush

  DOI：10.1021/ol0347388

  日期：2003.7.1

  [GRAPHICS]An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectivity. Subsequent amine displacement of the PFP moiety furnished functionalized sulfonamide products in good yields.
• A new route to 3,5-disubstituted isoxazolidines via the iodocyclization of homoallylic hydroxylamines
  作者：Fabrizio Mancini、Maria Giulia Piazza、Claudio Trombini

  DOI：10.1021/jo00013a032

  日期：1991.6

  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.