(1E)-1-[(1S,2R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-4-methyl-2-(2-methylprop-2-enoyl)cyclopentyl]-2,6,6-trimethylnona-1,8-dien-5-one | 1160556-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E)-1-[(1S,2R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-4-methyl-2-(2-methylprop-2-enoyl)cyclopentyl]-2,6,6-trimethylnona-1,8-dien-5-one
• CAS: 1160556-80-8
• 化学式: C₂₈H₄₈O₄Si
• 分子量: 476.772
• InChiKey: HOUKPYVKYZQVEB-HAXUJHTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1E)-1-[(1S,2R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-4-methyl-2-(2-methylprop-2-enoyl)cyclopentyl]-2,6,6-trimethylnona-1,8-dien-5-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (1R,2S,3aR,5E,12E,13aS)-1-[tert-butyl(dimethyl)silyl]oxy-3a-hydroxy-2,5,8,8,12-pentamethyl-2,3,7,10,11,13a-hexahydro-1H-cyclopenta[12]annulene-4,9-dione
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u
• 作为产物：
  描述：

  在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 以80%的产率得到(1E)-1-[(1S,2R,4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-2-hydroxy-4-methyl-2-(2-methylprop-2-enoyl)cyclopentyl]-2,6,6-trimethylnona-1,8-dien-5-one
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u