(1R,4S,5R,6S,8R)-4,5-bisallyl-8-methoxymethoxy-4,6,9,9-tetramethylbicyclo[4.3.0]-nonan-3-one | 1208239-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,5R,6S,8R)-4,5-bisallyl-8-methoxymethoxy-4,6,9,9-tetramethylbicyclo[4.3.0]-nonan-3-one
• 英文别名: (2R,3aR,6S,7R,7aS)-2-(methoxymethoxy)-3,3,6,7a-tetramethyl-6,7-bis(prop-2-enyl)-2,3a,4,7-tetrahydro-1H-inden-5-one
• CAS: 1208239-79-5
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: BPTUZKOLUOBZSE-ULZZIOJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (1R,4S,5R,6S,8R)-4,5-bisallyl-8-methoxymethoxy-4,6,9,9-tetramethylbicyclo[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,4R,6R,9S)-4-(methoxymethoxy)-2,5,5,9-tetramethyltricyclo[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
• 作为产物：
  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

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.