(1R,3aR,4R,5R,7aR)-1-hydroxy-5-methyl-3a,4,5,7a-tetrahydro-1H-indene-4-carboxylic acid ethyl ester | 1360564-63-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,3aR,4R,5R,7aR)-1-hydroxy-5-methyl-3a,4,5,7a-tetrahydro-1H-indene-4-carboxylic acid ethyl ester
• CAS: 1360564-63-1
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: ZWYSQSUMTWNQFT-LZQZFOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,3aR,4R,5R,7aR)-1-hydroxy-5-methyl-3a,4,5,7a-tetrahydro-1H-indene-4-carboxylic acid ethyl ester 在 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 8.0h， 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
• 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) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(1R,3aR,4R,5R,7aR)-1-hydroxy-5-methyl-3a,4,5,7a-tetrahydro-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