(3aR,4S,5S,6R,7S,7aS)-6,7-epoxy-5-methyl-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid ethyl ester | 1360564-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3aR,4S,5S,6R,7S,7aS)-6,7-epoxy-5-methyl-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid ethyl ester
• CAS: 1360564-68-6
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: KVHDHTYFXZEKBI-MSPHSMNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.9
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,5S,6R,7S,7aS)-6,7-epoxy-5-methyl-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid ethyl ester 在 silica gel 作用下， 以 环己烷 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Asymmetric Synthesis of the Oxygenated Polycyclic System of (+)-Harringtonolide

  摘要：

  A straightforward asymmetric synthesis of the cage oxygenated structure of (+)-harringtonolide has been accomplished for the first time. The key steps involved (i) a templated stereoselective IMDA reaction to build a highly functionalized cyclohexene ring D, (ii) functionalization of the cycloadduct, (iii) ring-closing metathesis providing the five-membered ring C, and finally (iv) a challenging one-step cascade cyclization of an epoxy-alcohol toward the target structure, whose mechanism was investigated.

  DOI：

  10.1021/ol300133x
• 作为产物：
  描述：

  (3R,4R,5R,6R)-6-[(R)-1'-hydroxyallyl]-3-methyl-5-[(E)-styryl]cyclohex-1-ene-4-carboxylic acid ethyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 二甲基二环氧乙烷 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 (3aR,4S,5S,6R,7S,7aS)-6,7-epoxy-5-methyl-1-oxo-3a,4,5,6,7,7a-hexahydro-1H-indene-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Oxygenated Polycyclic System of (+)-Harringtonolide

  摘要：

  A straightforward asymmetric synthesis of the cage oxygenated structure of (+)-harringtonolide has been accomplished for the first time. The key steps involved (i) a templated stereoselective IMDA reaction to build a highly functionalized cyclohexene ring D, (ii) functionalization of the cycloadduct, (iii) ring-closing metathesis providing the five-membered ring C, and finally (iv) a challenging one-step cascade cyclization of an epoxy-alcohol toward the target structure, whose mechanism was investigated.

  DOI：

  10.1021/ol300133x