1-(4-chlorobutyl)-2-nitrocyclohexene | 143238-80-6

• 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: 1-(4-chlorobutyl)-2-nitrocyclohexene
• CAS: 143238-80-6
• 化学式: C₁₀H₁₆ClNO₂
• 分子量: 217.696
• InChiKey: QHEJSMQISIOCSB-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±31.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-chlorobutyl methanesulfonate 、 1-ethylthio-2-nitrocyclohexene 生成 1-(4-chlorobutyl)-2-nitrocyclohexene
  参考文献：
  名称：

  Preparation of new classes of aliphatic, allylic, and benzylic zinc and copper reagents by the insertion of zinc dust into organic halides, phosphates, and sulfonates

  摘要：

  The insertion of zinc dust into primary alkyl chlorides, bromides, phosphates, and sulfonates in a polar solvent (DMPU, DMA) and in the presence of a catalytic amount of LiI (0.2 equiv) provides new organozinc reagents of the type RZnX (X = Cl, Br, OSO2R, OP(O)(OR)2) in excellent yields. After the transmetalation to the corresponding copper reagent RCu(CN)ZnX using CuCN.2LiCl, the addition of electrophiles, such as Michael acceptors, affords the desired adducts. Similarly, various new allylic and benzylic zinc reagents were prepared without the formation of any Wurtz-coupling side product and reacted with various electrophiles.

  DOI：

  10.1021/jo00046a026

文献信息

• Preparation of new classes of aliphatic, allylic, and benzylic zinc and copper reagents by the insertion of zinc dust into organic halides, phosphates, and sulfonates
  作者：Carole Jubert、Paul Knochel

  DOI：10.1021/jo00046a026

  日期：1992.9

  The insertion of zinc dust into primary alkyl chlorides, bromides, phosphates, and sulfonates in a polar solvent (DMPU, DMA) and in the presence of a catalytic amount of LiI (0.2 equiv) provides new organozinc reagents of the type RZnX (X = Cl, Br, OSO2R, OP(O)(OR)2) in excellent yields. After the transmetalation to the corresponding copper reagent RCu(CN)ZnX using CuCN.2LiCl, the addition of electrophiles, such as Michael acceptors, affords the desired adducts. Similarly, various new allylic and benzylic zinc reagents were prepared without the formation of any Wurtz-coupling side product and reacted with various electrophiles.