5-(furan-3-yl)-2-hydroxy-7'-methyl-3',4,5,5',5a',7',8',8a'-octahydrospiro[furan-3,6'-naphtho[1,8-bc]furan]-2'(4'H)-one | 136176-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5-(furan-3-yl)-2-hydroxy-7'-methyl-3',4,5,5',5a',7',8',8a'-octahydrospiro[furan-3,6'-naphtho[1,8-bc]furan]-2'(4'H)-one
• 英文别名: 5-(furan-3-yl)-2-hydroxy-7'-methyl-3',4,5,5',5a',7',8',8a'-octahydro-2H-spiro[furan-3,6'-naphtho[1,8-bc]furan]-2'(4'H)-one；(12S)-15,16-Epoxy-19-norneoclerodane-4,13(16),14-trien-18,6α-olide 20,12-hemiacetal
• CAS: 136176-66-4；136235-35-3
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: UUKKEAFOECOLNR-IUWPRIJWSA-N

物化性质

• 沸点：
  564.3±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  68.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(furan-3-yl)-2-hydroxy-7'-methyl-3',4,5,5',5a',7',8',8a'-octahydrospiro[furan-3,6'-naphtho[1,8-bc]furan]-2'(4'H)-one 在 chromium trioxide-pyridine complex 作用下， 以 吡啶 为溶剂， 反应 2.0h， 生成 山藿香素
  参考文献：
  名称：

  Transformation of neoclerodane diterpenoids into 19-norneoclerodane derivatives

  摘要：

  The neoclerodane diterpenoid eriocephalin (1) was transformed into its 19-nor derivatives 3 and 4 by reaction with potassium tert-butoxide in THF, whereas with the same treatment compound 6 yielded only the transacetylation derivative 7. These results indicated that 19-acetoxy-4-alpha,18-epoxy-7-alpha-hydroxy-6-oxoneoclerodane derivatives are transformed into the corresponding 19-nor compounds in a retroaldol reaction by loss of the C-19 carbon as formaldehyde followed by opening of the oxirane ring and intramolecular attack by a C-18 alkoxide on the carbonyl C-6 carbon atom, giving the allylic hemiacetal 3, which is easily dehydrated to the furanic derivative 4. Compound 4 was transformed into the alpha,beta-unsaturated gamma,delta-enol gamma-lactone 8 by an oxidation reaction with atomspheric oxygen in chloroform solution. Alternatively, it gave the alpha,beta-unsaturated gamma-lactone 11 under acid catalysis. These reactions allowed the partial syntheses of the naturally occurring diterpenoids teuscorolide (9) and teucvin (12) and are of interest for chemical transformations of substances of this kind.

  DOI：

  10.1021/jo00023a027
• 作为产物：
  描述：

  eriocephalin 在 硫酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 5-(furan-3-yl)-2-hydroxy-7'-methyl-3',4,5,5',5a',7',8',8a'-octahydrospiro[furan-3,6'-naphtho[1,8-bc]furan]-2'(4'H)-one
  参考文献：
  名称：

  Transformation of neoclerodane diterpenoids into 19-norneoclerodane derivatives

  摘要：

  The neoclerodane diterpenoid eriocephalin (1) was transformed into its 19-nor derivatives 3 and 4 by reaction with potassium tert-butoxide in THF, whereas with the same treatment compound 6 yielded only the transacetylation derivative 7. These results indicated that 19-acetoxy-4-alpha,18-epoxy-7-alpha-hydroxy-6-oxoneoclerodane derivatives are transformed into the corresponding 19-nor compounds in a retroaldol reaction by loss of the C-19 carbon as formaldehyde followed by opening of the oxirane ring and intramolecular attack by a C-18 alkoxide on the carbonyl C-6 carbon atom, giving the allylic hemiacetal 3, which is easily dehydrated to the furanic derivative 4. Compound 4 was transformed into the alpha,beta-unsaturated gamma,delta-enol gamma-lactone 8 by an oxidation reaction with atomspheric oxygen in chloroform solution. Alternatively, it gave the alpha,beta-unsaturated gamma-lactone 11 under acid catalysis. These reactions allowed the partial syntheses of the naturally occurring diterpenoids teuscorolide (9) and teucvin (12) and are of interest for chemical transformations of substances of this kind.

  DOI：

  10.1021/jo00023a027