3-(4'-methylcyclohex-3'-en-1-yl)but-2-enyl bromide | 73494-01-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(4'-methylcyclohex-3'-en-1-yl)but-2-enyl bromide
• 英文别名: (Z)-1-bromo-(4-methyl-3-cyclohexen-1-yl)-2-butene；4-[(Z)-4-bromobut-2-en-2-yl]-1-methylcyclohexene
• CAS: 73494-01-6
• 化学式: C₁₁H₁₇Br
• 分子量: 229.16
• InChiKey: OJGVTTGQEKAAIR-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  3-(4'-methylcyclohex-3'-en-1-yl)but-2-enyl bromide 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 lithium aluminium tetrahydride 、 水 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.08h， 生成 (Z)-α-bisabolene
  参考文献：
  名称：

  Vig, O. P.; Kad, G. L., Journal of the Indian Chemical Society, 1987, vol. 64, p. 756 - 757

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基环己-3-烯-1-羧酸 在 吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 甲基锂 、 三溴化磷 、 二异丁基氢化铝 、 三苯基膦 、 pyridinium chlorochromate 、 锌 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 216.5h， 生成 3-(4'-methylcyclohex-3'-en-1-yl)but-2-enyl bromide
  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

• VIG, O. P.;KAD, G. L., J. INDIAN CHEM. SOC., 64,(1987) N 12, 756-757
  作者：VIG, O. P.、KAD, G. L.

  DOI：——

  日期：——
• 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.
• Vig, O. P.; Kad, G. L., Journal of the Indian Chemical Society, 1987, vol. 64, p. 756 - 757
  作者：Vig, O. P.、Kad, G. L.

  DOI：——

  日期：——