(Z)-α-Propyl-N-(1-buten-3-yl)nitrone | 127279-70-3

• 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: (Z)-α-Propyl-N-(1-buten-3-yl)nitrone
• 英文别名: (Z)-α-n-propyl-N-(1-buten-3-yl)nitrone；N-but-3-en-2-ylbutan-1-imine oxide
• CAS: 127279-70-3
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: HCYJCXBIVMYUBW-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (Z)-α-Propyl-N-(1-buten-3-yl)nitrone 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 α-Ethenyl-α-methyl-N-butylnitrone
  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
• 作为产物：
  描述：

  1-硝基丁烷 、 丁-2-烯氯化镁 以 四氢呋喃 为溶剂， 反应 0.25h， 以58%的产率得到(Z)-α-Propyl-N-(1-buten-3-yl)nitrone
  参考文献：
  名称：

  Reaction of aryl and alkyl nitro compounds with 2-butenylmagnesium chloride: synthesis of a new class of nitrones

  摘要：

  DOI：

  10.1021/jo00301a046

文献信息

• Reaction of aryl and alkyl nitro compounds with 2-butenylmagnesium chloride: synthesis of a new class of nitrones
  作者：Giuseppe Bartoli、Enrico Marcantoni、Marino Petrini、Renato Dalpozzo

  DOI：10.1021/jo00301a046

  日期：1990.7
• 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.