(3RS,4SR)-3,4-dimethyl-1-(4-methylpent-3-enyl)-4-(prop-1-en-2-yl)cyclohex-1-ene

• 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: (3RS,4SR)-3,4-dimethyl-1-(4-methylpent-3-enyl)-4-(prop-1-en-2-yl)cyclohex-1-ene
• 英文别名: (3R,4S)-3,4-dimethyl-1-(4-methylpent-3-enyl)-4-prop-1-en-2-ylcyclohexene
• 化学式: C₁₇H₂₈
• 分子量: 232.409
• InChiKey: MRFGJRIBLDEVMW-NVXWUHKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (-)-1-[1,2-dimethyl-4-(4-methyl-pent-3-enyl)-cyclohex-3-enyl]-ethanone 、 二甲基氯化铝 以 正己烷 为溶剂， 反应 730.5h， 以30%的产率得到(3RS,4SR)-3,4-dimethyl-1-(4-methylpent-3-enyl)-4-(prop-1-en-2-yl)cyclohex-1-ene
  参考文献：
  名称：

  Cyclization of 1,5-Dienes:  An Efficient Synthesis of β-Georgywood

  摘要：

  In the acid-promoted 1,5-diene cyclization of pseudo- to beta-Georgywood, the cyclization product is obtained with high selectivity in spite of an unfavorable substituent at the C(2)-position of the diene precursor. Preisomerization of the cyclohexene double bond, which occurs in the presence of Bronsted acids, is suppressed with > 1 equiv of MXn-type Lewis acids, whereas RAlX2-type Lewis acids such as > 2 equiv of MeAlCl2 have the additional benefit of steering the double bond of the cyclized product into the desired beta-position. Mechanistic studies revealed a crucial participation or nonparticipation of the carbonyl group in the cyclization reaction, depending on the acid family employed, and allowed finally the development of a cyclization reaction catalyzed by MeAlCl2 that can be generated in situ from precatalyst AlMe3.(1).

  DOI：

  10.1021/jo061668k

文献信息

• Cyclization of 1,5-Dienes:  An Efficient Synthesis of β-Georgywood
  作者：Georg Fráter、Fridtjof Schröder

  DOI：10.1021/jo061668k

  日期：2007.2.1

  In the acid-promoted 1,5-diene cyclization of pseudo- to beta-Georgywood, the cyclization product is obtained with high selectivity in spite of an unfavorable substituent at the C(2)-position of the diene precursor. Preisomerization of the cyclohexene double bond, which occurs in the presence of Bronsted acids, is suppressed with > 1 equiv of MXn-type Lewis acids, whereas RAlX2-type Lewis acids such as > 2 equiv of MeAlCl2 have the additional benefit of steering the double bond of the cyclized product into the desired beta-position. Mechanistic studies revealed a crucial participation or nonparticipation of the carbonyl group in the cyclization reaction, depending on the acid family employed, and allowed finally the development of a cyclization reaction catalyzed by MeAlCl2 that can be generated in situ from precatalyst AlMe3.(1).