methyl 3-(4-methyl-3-cyclohexen-1-yl)propynoate | 162132-41-4

• 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: methyl 3-(4-methyl-3-cyclohexen-1-yl)propynoate
• 英文别名: Methyl 3-(4-methylcyclohex-3-en-1-yl)prop-2-ynoate
• CAS: 162132-41-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: RZDSUFFHDQLNKF-UHFFFAOYSA-N

物化性质

• 沸点：
  274.2±20.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-methyl-3-cyclohexen-1-yl)propynoate 在 吡啶 、 copper(l) iodide 、 sodium 、 三溴化磷 、 lithium 、 二异丁基氢化铝 、 氯化铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 19.0h， 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 、 甲基锂 、 三苯基膦 、 pyridinium chlorochromate 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 197.5h， 生成 methyl 3-(4-methyl-3-cyclohexen-1-yl)propynoate
  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.