(1S,6S,8R)-8-methoxymethoxy-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-one | 1208239-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,6S,8R)-8-methoxymethoxy-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-one
• 英文别名: (2R,3aS,7aS)-2-(methoxymethoxy)-1,1,3a,5-tetramethyl-2,3,7,7a-tetrahydroinden-4-one
• CAS: 1208239-78-4
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: HKDOIDGFXUVDGU-ZOWXZIJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,6S,8R)-8-methoxymethoxy-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-one 、 3-溴丙烯 在 lithium 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.03h， 以88%的产率得到(1S,2S,6S,8R)-2-allyl-8-(methoxymethoxy)-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-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
• 作为产物：
  描述：

  (1S,6S,8R)-8-hydroxy-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-one 、 氯甲基甲基醚 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 以92%的产率得到(1S,6S,8R)-8-methoxymethoxy-1,3,7,7-tetramethylbicyclo[4.3.0]non-3-en-2-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.