(1S,2S,6S,8S)-2-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-8-ol | 1208239-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,6S,8S)-2-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-8-ol
• CAS: 1208239-91-1
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: TVLIPELJAVNTQO-ABHRYQDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,6S,8S)-2-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-8-ol 、 氯化苄 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以86%的产率得到(1S,2S,6S,8S)-8-benzyloxy-2-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-ene
  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
• 作为产物：
  描述：

  methyl [(1S,2S,6S)-2-(2-methoxymethoxy)-1,3-dimethyl-6-isopropenylcyclohex-3-enyl]acetate 在 氨 、 lithium 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 (1S,2S,6S,8S)-2-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-8-ol 、 (1S,2S,6S,8R)-2-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-8-ol
  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