(3R,4R,4aS,5R,8aS)-4-Hydroxy-3-(1-hydroxy-1-methyl-ethyl)-4a,5-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one | 615577-64-5

• 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: (3R,4R,4aS,5R,8aS)-4-Hydroxy-3-(1-hydroxy-1-methyl-ethyl)-4a,5-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one
• 英文别名: (3R,4R,4aS,5R,8aS)-4-hydroxy-3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-2,3,4,5,8,8a-hexahydronaphthalen-1-one
• CAS: 615577-64-5
• 化学式: C₁₅H₂₄O₃
• 分子量: 252.354
• InChiKey: DJCXZIKHCVBHPS-DAHVATMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R,4aS,5R,8aS)-4-Hydroxy-3-(1-hydroxy-1-methyl-ethyl)-4a,5-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 以92%的产率得到(3R,4R,4aS,5S,6R,7S,8aS)-4,6,7-Trihydroxy-3-(1-hydroxy-1-methyl-ethyl)-4a,5-dimethyl-octahydro-naphthalen-1-one
  参考文献：
  名称：

  A general, ring closure metathesis based enantiospecific approach to polyfunctional eudesmane, eremophilane and agarofuran sesquiterpenoids

  摘要：

  An enantiospecific and stereo- and functional group diversity oriented approach to eudesmane, eremophilane and agarofuran sesquiterpenoids from (-)-carvone has been devised. RCM has been employed as the key reaction to generate the highly functionalized eudesmane framework. Further elaboration of the eudesmane framework to agarofurans and biogenetic-type rearrangement to eremophilanes is Outlined. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01757-x
• 作为产物：
  描述：

  Benzoic acid (1R,3R,4aR,5R,8aS)-4a-hydroxy-3-isopropenyl-5,8a-dimethyl-1,2,3,4,4a,5,8,8a-octahydro-naphthalen-1-yl ester 在 氯化亚砜 、 三氟化硼乙醚 、 mercury(II) diacetate 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (3R,4R,4aS,5R,8aS)-4-Hydroxy-3-(1-hydroxy-1-methyl-ethyl)-4a,5-dimethyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  A general, ring closure metathesis based enantiospecific approach to polyfunctional eudesmane, eremophilane and agarofuran sesquiterpenoids

  摘要：

  An enantiospecific and stereo- and functional group diversity oriented approach to eudesmane, eremophilane and agarofuran sesquiterpenoids from (-)-carvone has been devised. RCM has been employed as the key reaction to generate the highly functionalized eudesmane framework. Further elaboration of the eudesmane framework to agarofurans and biogenetic-type rearrangement to eremophilanes is Outlined. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01757-x