methyl 5-{2-[1-(2-aminophenyl)-2-oxo-2,5-dihdyro-1H-pyrrol-3-yl]ethyl}-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate | 933046-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl 5-{2-[1-(2-aminophenyl)-2-oxo-2,5-dihdyro-1H-pyrrol-3-yl]ethyl}-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate
• CAS: 933046-23-2
• 化学式: C₂₇H₃₆N₂O₃
• 分子量: 436.594
• InChiKey: IRMRVEHRQRNIOZ-CYDBCKOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 5-{2-[1-(2-aminophenyl)-2-oxo-2,5-dihdyro-1H-pyrrol-3-yl]ethyl}-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate 、 乙酸酐 在 sodium acetate 作用下， 反应 2.0h， 以64%的产率得到methyl 5-{2-[1-(2-acetylaminophenyl)-2-oxo-2,5-dihdyro-1H-pyrrol-3-yl]ethyl}-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XIV. Synthesis of pyrrololabdanoids from lambertianic acid

  摘要：

  Treatment of lambertianic acid methyl ester with lead tetraacetate gave terpenoid 2,5-diacetoxydihydrofuran which reacted with primary amines to yield 3 -terpenyl -substituted pyrrol-2(5H)-ones; the reaction with bydrazine led to the corresponding pyridazine derivative. The obtained furanoterpenoids underwent oxidative methoxylation by the action of N-chlorobenzenesulfonamide or N-bromosuccinimide in methanol. 2,5-Dimethoxydihydrofurans thus formed were smoothly converted into 3-substituted furan-2(5H)-one in acid medium. Hydrogenation of 2,5-dimethoxydihydrofurans, followed by treatment with amines, gave 1,3-disubstituted pyrroles.

  DOI：

  10.1134/s1070428006060030
• 作为产物：
  描述：

  lambertianic acid methyl ester 在 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.17h， 生成 methyl 5-{2-[1-(2-aminophenyl)-2-oxo-2,5-dihdyro-1H-pyrrol-3-yl]ethyl}-1,4a-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XIV. Synthesis of pyrrololabdanoids from lambertianic acid

  摘要：

  Treatment of lambertianic acid methyl ester with lead tetraacetate gave terpenoid 2,5-diacetoxydihydrofuran which reacted with primary amines to yield 3 -terpenyl -substituted pyrrol-2(5H)-ones; the reaction with bydrazine led to the corresponding pyridazine derivative. The obtained furanoterpenoids underwent oxidative methoxylation by the action of N-chlorobenzenesulfonamide or N-bromosuccinimide in methanol. 2,5-Dimethoxydihydrofurans thus formed were smoothly converted into 3-substituted furan-2(5H)-one in acid medium. Hydrogenation of 2,5-dimethoxydihydrofurans, followed by treatment with amines, gave 1,3-disubstituted pyrroles.

  DOI：

  10.1134/s1070428006060030