1-methoxy-4,4,7-trimethyl-4,4a,5,6-tetrahydro-3H-isochromen-3-one | 1191906-29-2

• 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: 1-methoxy-4,4,7-trimethyl-4,4a,5,6-tetrahydro-3H-isochromen-3-one
• 英文别名: 1-methoxy-4,4,7-trimethyl-5,6-dihydro-4aH-isochromen-3-one
• CAS: 1191906-29-2
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: OCYSVRYHBGCUCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methoxy-4,4,7-trimethyl-4,4a,5,6-tetrahydro-3H-isochromen-3-one 、 乙烯基溴化镁 以 四氢呋喃 为溶剂， 反应 3.0h， 以29%的产率得到rac-(4aS,8aS)-methyl 1,1,6-trimethyl-2-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalene-4a-carboxylate
  参考文献：
  名称：

  A Novel Cis-Selective Cyclohexanone Annulation as the Key Step of a Total Synthesis of the Sesquiterpene Isoacanthodoral

  摘要：

  Isoacanthodoral (1) is a structurally unique sesquiterpene in that it is a bicyclo[4.4.0]dec-1-ene with a cis-rather than the common trans-junction between the constituting rings. An efficient construction of this motif has been accomplished by a novel cis-selective cyclohexanone annulation, combining the lithium enolate of ester 8, the alpha,beta-unsaturated ester 6, and vinylmagnesium bromide in a single synthetic operation. For completing the total synthesis of 1, a Shapiro-olefination/hydrogenation sequence and a reductive cyanation were employed.

  DOI：

  10.1021/ol9018979
• 作为产物：
  描述：

  异丁酸苯酯 、 甲基5-甲基-1,5-环己二烯-1-羧酸酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.42h， 以10%的产率得到1-methoxy-4,4,7-trimethyl-4,4a,5,6-tetrahydro-3H-isochromen-3-one
  参考文献：
  名称：

  A Novel Cis-Selective Cyclohexanone Annulation as the Key Step of a Total Synthesis of the Sesquiterpene Isoacanthodoral

  摘要：

  Isoacanthodoral (1) is a structurally unique sesquiterpene in that it is a bicyclo[4.4.0]dec-1-ene with a cis-rather than the common trans-junction between the constituting rings. An efficient construction of this motif has been accomplished by a novel cis-selective cyclohexanone annulation, combining the lithium enolate of ester 8, the alpha,beta-unsaturated ester 6, and vinylmagnesium bromide in a single synthetic operation. For completing the total synthesis of 1, a Shapiro-olefination/hydrogenation sequence and a reductive cyanation were employed.

  DOI：

  10.1021/ol9018979