(1R,3aR,4R,5R,7aR)-5-methyl-3-oxo-1-vinyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-4-carboxylic acid ethyl ester | 1360564-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (1R,3aR,4R,5R,7aR)-5-methyl-3-oxo-1-vinyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-4-carboxylic acid ethyl ester
• CAS: 1360564-54-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: NALNILSLBVNTCG-IYKVGLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3aR,4R,5R,7aR)-5-methyl-3-oxo-1-vinyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-4-carboxylic acid ethyl ester 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以91%的产率得到(1R,3R,3aR,4R,5R,7aR)-3-hydroxy-5-methyl-1-vinyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-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：

  在 咪唑 、 盐酸 、 水 、 碘 、 三苯基膦 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 48.67h， 生成 (1R,3aR,4R,5R,7aR)-5-methyl-3-oxo-1-vinyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-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