(1R,6S,8R)-5-allyl-8-(methoxymethoxy)-4,6,9,9-tetramethylbicyclo[4.3.0]non-4-en-3-one | 1208239-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,6S,8R)-5-allyl-8-(methoxymethoxy)-4,6,9,9-tetramethylbicyclo[4.3.0]non-4-en-3-one
• CAS: 1208239-81-9
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: REXUQFPNLKQOTP-LZLYRXPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,6S,8R)-5-allyl-8-(methoxymethoxy)-4,6,9,9-tetramethylbicyclo[4.3.0]non-4-en-3-one 、 3-溴丙烯 在 氨 、 lithium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.84h， 以70%的产率得到(1R,4S,5R,6S,8R)-4,5-bisallyl-8-methoxymethoxy-4,6,9,9-tetramethylbicyclo[4.3.0]-nonan-3-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
• 作为产物：
  描述：

  (1S,2S,6S,8R)-2-allyl-8-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-ol 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以90%的产率得到(1R,6S,8R)-5-allyl-8-(methoxymethoxy)-4,6,9,9-tetramethylbicyclo[4.3.0]non-4-en-3-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