11-methoxy-4,4,7-trimethyl-1,2,3,5-tetrahydro-8-oxadibenzo[a,h]azulene | 672288-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 11-methoxy-4,4,7-trimethyl-1,2,3,5-tetrahydro-8-oxadibenzo[a,h]azulene
• 英文别名: 16-Methoxy-6,6,10-trimethyl-12-oxatetracyclo[9.7.0.02,7.013,18]octadeca-1(11),2(7),9,13(18),14,16-hexaene
• CAS: 672288-29-8
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: MAKSUXLRUXIRIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-methoxy-4,4,7-trimethyl-1,2,3,5-tetrahydro-8-oxadibenzo[a,h]azulene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以90%的产率得到(+/-)-O-methyl-frondosin B
  参考文献：
  名称：

  Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

  摘要：

  A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8pi-electrocyclization is proposed to explain the formation of this ring-expanded species.

  DOI：

  10.1021/ol035822q
• 作为产物：
  描述：

  2-烯丙基-3-(2-异丙烯基-5-甲氧基苯并呋喃-3-基)-环己-2-烯酮 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四氯化钛 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 21.25h， 生成 11-methoxy-4,4,7-trimethyl-1,2,3,5-tetrahydro-8-oxadibenzo[a,h]azulene
  参考文献：
  名称：

  Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue

  摘要：

  A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8pi-electrocyclization is proposed to explain the formation of this ring-expanded species.

  DOI：

  10.1021/ol035822q

文献信息

• Multicomponent Coupling Approach to (±)-Frondosin B and a Ring-Expanded Analogue
  作者：Daniel J. Kerr、Anthony C. Willis、Bernard L. Flynn

  DOI：10.1021/ol035822q

  日期：2004.2.1

  A recently discovered multicomponent coupling reaction is used to give direct access to a late intermediate in the synthesis of frondosin B. This intermediate can also be efficiently converted to a ring-expanded analogue of frondosin B by sustained heating of the reaction mixture. An unprecedented tandem 1,7-hydrogen shift, 8pi-electrocyclization is proposed to explain the formation of this ring-expanded species.