silphiperfol-6,9(15)-diene | 1370360-61-4

• 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: silphiperfol-6,9(15)-diene
• 英文别名: (1R,5S,8S)-9-methylene-2,3,5-trimethyltricyclo[6.3.0.01,5]undec-2-ene
• CAS: 1370360-61-4
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: ZAYINISZQHLVAE-KKUMJFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  silphiperfol-6,9(15)-diene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 正己烷 为溶剂， 反应 1.5h， 生成 (1R,5S,8S)-2,3,5,9-tetramethyltricyclo[6.3.0.01,5]undec-2-ene 、 (1R,5S,8S)-2,3,5,9-tetramethyltricyclo[6.3.0.01,5]undec-2-ene
  参考文献：
  名称：

  The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene

  摘要：

  The enantiospecific total synthesis of silphiperfol-6-ene has been accomplished starting from the readily available monoterpene (R)-limonene, employing a rhodium carbenoid insertion into the CH bond of a tertiary methyl group. A substrate dependent competitive insertion of the rhodium carbenoid in the gamma- and beta-CH bonds to form cyclopentanone and cyclobutanones, respectively, has been described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.016
• 作为产物：
  描述：

  ethyl 3-[(1R,2R,5S)-1,5,7,8-tetramethylbicyclo[3.3.0]oct-7-en-2-yl]-3-oxopropanoate 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 potassium 2-methylbutan-2-olate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 13.5h， 生成 silphiperfol-6,9(15)-diene
  参考文献：
  名称：

  The substrate dependent competitive formation of cyclobutanones and cyclopentanones in an intramolecular rhodium carbenoid CH insertion reaction: enantiospecific total synthesis of silphiperfol-6-ene

  摘要：

  The enantiospecific total synthesis of silphiperfol-6-ene has been accomplished starting from the readily available monoterpene (R)-limonene, employing a rhodium carbenoid insertion into the CH bond of a tertiary methyl group. A substrate dependent competitive insertion of the rhodium carbenoid in the gamma- and beta-CH bonds to form cyclopentanone and cyclobutanones, respectively, has been described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.01.016