(Z)-α-Phenyl-N-(1-carbomethoxy-3-butyl)nitrone | 143957-88-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-α-Phenyl-N-(1-carbomethoxy-3-butyl)nitrone
• 英文别名: N-(5-methoxy-5-oxopentan-2-yl)-1-phenylmethanimine oxide
• CAS: 143957-88-4
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: WEMGLBYNQCXITP-UVTDQMKNSA-N

物化性质

• 沸点：
  371.9±44.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-硝基戊烷酸甲酯 、 苄基溴化镁 以 四氢呋喃 为溶剂， 以66%的产率得到(Z)-α-Phenyl-N-(1-carbomethoxy-3-butyl)nitrone
  参考文献：
  名称：

  Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction

  摘要：

  Reaction of allyl and benzyl Grignard reagents with functionalized nitroalkanes affords nitrones in good yield. This process shows considerable chemoselectivity; carbonyl groups and other highly reactive electrophilic functions are unaffected by the reaction conditions (THF, -70-degrees-C). A mixture of regioisomers 4 and 5 is usually obtained, and the product distribution depends on the nature of the alkyl framework. An intermediate 3 is postulated, and the isomeric pair of nitrones arises, very likely through a selective syn elimination. Alpha-substituted alkyl chains give mostly conjugated products 4 while unbranched chains afford predominantly the nonconjugated nitrones 5. The 4/5 ratio can be strongly modified by using a proton source of suitable strength; trichloroacetic acid produces 4 exclusively in the reaction of nitroethane with benzyl Grignard, while 2,6-dimethylphenol affords completely the nonconjugated nitrone 5. The stereochemistry of the double bond is affected by the nature of the reagent used. Benzyl Grignard gives only Z nitrones 4 and 5; 2-butenylmagnesium chloride gives nonconjugated Z nitrones and a predominance of E isomer in the conjugated nitrone 5.

  DOI：

  10.1021/jo00048a012

文献信息

• Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction
  作者：Giuseppe Bartoli、Enrico Marcantoni、Marino Petrini

  DOI：10.1021/jo00048a012

  日期：1992.10

  Reaction of allyl and benzyl Grignard reagents with functionalized nitroalkanes affords nitrones in good yield. This process shows considerable chemoselectivity; carbonyl groups and other highly reactive electrophilic functions are unaffected by the reaction conditions (THF, -70-degrees-C). A mixture of regioisomers 4 and 5 is usually obtained, and the product distribution depends on the nature of the alkyl framework. An intermediate 3 is postulated, and the isomeric pair of nitrones arises, very likely through a selective syn elimination. Alpha-substituted alkyl chains give mostly conjugated products 4 while unbranched chains afford predominantly the nonconjugated nitrones 5. The 4/5 ratio can be strongly modified by using a proton source of suitable strength; trichloroacetic acid produces 4 exclusively in the reaction of nitroethane with benzyl Grignard, while 2,6-dimethylphenol affords completely the nonconjugated nitrone 5. The stereochemistry of the double bond is affected by the nature of the reagent used. Benzyl Grignard gives only Z nitrones 4 and 5; 2-butenylmagnesium chloride gives nonconjugated Z nitrones and a predominance of E isomer in the conjugated nitrone 5.