1-((1SR,2RS)-3-deuterio-1,2-dimethyl-4-(4-methylpent-3-enyl)cyclohex-3-enyl)ethanone

• 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: 1-((1SR,2RS)-3-deuterio-1,2-dimethyl-4-(4-methylpent-3-enyl)cyclohex-3-enyl)ethanone
• 英文别名: 1-[(1S,2R)-3-deuterio-1,2-dimethyl-4-(4-methylpent-3-enyl)cyclohex-3-en-1-yl]ethanone
• 化学式: C₁₆H₂₆O
• 分子量: 235.374
• InChiKey: WVXAQUSBMRDRSY-BDRNMSGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-((1SR,2RS)-3-deuterio-1,2-dimethyl-4-(4-methylpent-3-enyl)cyclohex-3-enyl)ethanone 在 磷酸 作用下， 以 xylene 为溶剂， 反应 2.0h， 生成 1-((cis)-1,2,3,4,5,6,7,8-octahydro-1,1,7,8-tetramethylnaphthalen-7-yl)-2-deuterio-ethanone 、 1-((5RS,6RS,7SR)-5-deuter1,2,4,5,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalen-7-yl)-2-deuterio-ethanone
  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
• 作为产物：
  描述：

  (E)-3-deuterio-4,8-dimethylnona-2,7-dien-4-ol 在 正丁基锂 、 三氟化硼乙醚 、 氯甲酸乙酯 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.33h， 生成 1-((1SR,2RS)-3-deuterio-1,2-dimethyl-4-(4-methylpent-3-enyl)cyclohex-3-enyl)ethanone
  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).