(1R,2S,6R,9S)-2,5,5,9-tetramethyl-4-methylenetricyclo[7.4.0.0(2,6)]tridec-11-en-8-one | 1208239-90-0

• 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: (1R,2S,6R,9S)-2,5,5,9-tetramethyl-4-methylenetricyclo[7.4.0.0(2,6)]tridec-11-en-8-one
• 英文别名: (3aR,5aS,9aR,9bS)-3,3,5a,9b-tetramethyl-2-methylidene-1,3a,4,6,9,9a-hexahydrocyclopenta[a]naphthalen-5-one
• CAS: 1208239-90-0
• 化学式: C₁₈H₂₆O
• 分子量: 258.404
• InChiKey: IMUOFHYGFPSXOK-DFEHZGFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1R,4S,5R,6S)-4,5-bisallyl-4,6,9,9-tetramethyl-8-methylenebicyclo[4.3.0]nonan-3-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到(1R,2S,6R,9S)-2,5,5,9-tetramethyl-4-methylenetricyclo[7.4.0.0(2,6)]tridec-11-en-8-one
  参考文献：
  名称：

  Enantiospecific synthesis of ABC-ring system of A-nor and abeo 4(3→2) tetra and pentacyclic triterpenes

  摘要：

  Enantiospecific synthesis of ABC-ring systems of A-nor and abeo 4(3 -> 2) tetra and pentacyclic triterpenes has been accomplished starting from the readily available monoterpene (R)-carvone. (R)-Carvone was used as the B-ring of the target molecules. A lithium-liquid ammonia mediated cyclisation of delta,epsilon-unsaturated ester was employed for the cyclopentannulation at the C-5 and C-6 carbons of carvone and an RCM reaction was employed for the cyclohexannulation to generate the ABC-ring system of A-nor tetra and pentacyclic triterpenes. The strategy has been extended for the synthesis of the ABC-ring system of abeo 4(3 -> 2) tetra and pentacyclic triterpenes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.114

文献信息

• Enantiospecific synthesis of ABC-ring system of A-nor and abeo 4(3→2) tetra and pentacyclic triterpenes
  作者：A. Srikrishna、R. Ramesh Babu、B. Beeraiah

  DOI：10.1016/j.tet.2009.11.114

  日期：2010.1

  Enantiospecific synthesis of ABC-ring systems of A-nor and abeo 4(3 -> 2) tetra and pentacyclic triterpenes has been accomplished starting from the readily available monoterpene (R)-carvone. (R)-Carvone was used as the B-ring of the target molecules. A lithium-liquid ammonia mediated cyclisation of delta,epsilon-unsaturated ester was employed for the cyclopentannulation at the C-5 and C-6 carbons of carvone and an RCM reaction was employed for the cyclohexannulation to generate the ABC-ring system of A-nor tetra and pentacyclic triterpenes. The strategy has been extended for the synthesis of the ABC-ring system of abeo 4(3 -> 2) tetra and pentacyclic triterpenes. (C) 2009 Elsevier Ltd. All rights reserved.