1,1-二溴-2-(4-甲基-3-环己烯-1-基)乙烯 | 162132-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1-二溴-2-(4-甲基-3-环己烯-1-基)乙烯
• 英文名称: 1,1-dibromo-2-(4-methyl-3-cyclohexen-1-yl)ethene
• 英文别名: 4-(2,2-Dibromoethenyl)-1-methylcyclohexene
• CAS: 162132-39-0
• 化学式: C₉H₁₂Br₂
• 分子量: 280.002
• InChiKey: ZIJKVTVPSLMQKU-UHFFFAOYSA-N

物化性质

• 沸点：
  269.4±28.0 °C(Predicted)
• 密度：
  1.714±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1-二溴-2-(4-甲基-3-环己烯-1-基)乙烯 在 吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 甲基锂 、 sodium 、 三溴化磷 、 lithium 、 氯化铵 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 42.5h， 生成 (E)‐α‐bisabolene
  参考文献：
  名称：

  Termite Trail Attractants: New Syntheses of Racemic (E)-α-, (Z)-α- andβ-Bisabolenes

  摘要：

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.

  DOI：

  10.1080/00397919408010239
• 作为产物：
  描述：

  4-甲基环己-3-烯-1-羧酸 在 lithium aluminium tetrahydride 、 三苯基膦 、 pyridinium chlorochromate 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 176.5h， 生成 1,1-二溴-2-(4-甲基-3-环己烯-1-基)乙烯
  参考文献：
  名称：

  Termite Trail Attractants: New Syntheses of Racemic (E)-α-, (Z)-α- andβ-Bisabolenes

  摘要：

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.

  DOI：

  10.1080/00397919408010239

文献信息

• Termite Trail Attractants: New Syntheses of Racemic (<i>E</i>)-<i>α</i>-, (<i>Z</i>)-<i>α</i>- and<i>β</i>-Bisabolenes
  作者：Laura Argenti、Fabio Bellina、Adriano Carpita、Nicola Dell'Amico、Renzo Rossi

  DOI：10.1080/00397919408010239

  日期：1994.12

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.