(5aS,6R,7R)-6-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-7-methyl-4,5,5a,6,7,8-hexahydro-3H-naphtho[1,8-bc]furan-6-carboxylic acid methyl ester | 139092-01-6

• 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: (5aS,6R,7R)-6-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-7-methyl-4,5,5a,6,7,8-hexahydro-3H-naphtho[1,8-bc]furan-6-carboxylic acid methyl ester
• CAS: 139092-01-6
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: FMTNRNDSZNXLNN-WWRLMZBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.81
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5aS,6R,7R)-6-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-7-methyl-4,5,5a,6,7,8-hexahydro-3H-naphtho[1,8-bc]furan-6-carboxylic acid methyl ester 在 chromium trioxide-pyridine complex 作用下， 以 吡啶 为溶剂， 以47%的产率得到(5aS,6R,7R)-6-(2-Furan-3-yl-2-oxo-ethyl)-7-methyl-4,5,5a,6,7,8-hexahydro-3H-naphtho[1,8-bc]furan-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Transformation of montanin A into isocrotocaudin. A revision of the structures of crotocaudin and isocrotocaudin

  摘要：

  Starting from montanin A (3) compound 11 was obtained by opening of the C-20,C-12 gamma-lactone (6), oxidation of the C-12 hydroxyl group (9), relactonization to the beta, gamma-unsaturated gamma-lactone (10) via the C-12 enol form, and final selective air oxidation of the alpha,beta,beta'-trialkyl furan to the corresponding alpha,beta-unsaturated gamma-lactone (11). Compound 11 was identical to isocrotocaudin, to which structure 1 has previously been assigned only on spectroscopic grounds. The above transformation establishes that the previous 8S configuration of isocrotocaudin (1) and its related C-6,C-10 stereoisomer crotocaudin (2) must be corrected to 8R.

  DOI：

  10.1016/0040-4039(91)80505-z
• 作为产物：
  描述：

  (5'aS,3R,5S)-5-(3-呋喃基)-3',4,4',5,5',5'a,7',8'-八氢-7'alpha-甲基螺[呋喃-3(2H),6'-[6H]萘并[1,8-bc]呋喃]-2-酮 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 生成 (5aS,6R,7R)-6-((S)-2-Furan-3-yl-2-hydroxy-ethyl)-7-methyl-4,5,5a,6,7,8-hexahydro-3H-naphtho[1,8-bc]furan-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Transformation of montanin A into isocrotocaudin. A revision of the structures of crotocaudin and isocrotocaudin

  摘要：

  Starting from montanin A (3) compound 11 was obtained by opening of the C-20,C-12 gamma-lactone (6), oxidation of the C-12 hydroxyl group (9), relactonization to the beta, gamma-unsaturated gamma-lactone (10) via the C-12 enol form, and final selective air oxidation of the alpha,beta,beta'-trialkyl furan to the corresponding alpha,beta-unsaturated gamma-lactone (11). Compound 11 was identical to isocrotocaudin, to which structure 1 has previously been assigned only on spectroscopic grounds. The above transformation establishes that the previous 8S configuration of isocrotocaudin (1) and its related C-6,C-10 stereoisomer crotocaudin (2) must be corrected to 8R.

  DOI：

  10.1016/0040-4039(91)80505-z