methyl 3a-hydroxymethyl-2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)-6,9a-dimethyldodecahydronaphtho[2,1-b]furan-6-carboxylate | 933046-28-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 3a-hydroxymethyl-2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)-6,9a-dimethyldodecahydronaphtho[2,1-b]furan-6-carboxylate
• CAS: 933046-28-7
• 化学式: C₂₃H₃₆O₇
• 分子量: 424.535
• InChiKey: NPLYZBUOPDCQRP-SLNLBUQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 3a-hydroxymethyl-2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)-6,9a-dimethyldodecahydronaphtho[2,1-b]furan-6-carboxylate 在 镍 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以72%的产率得到(2S,3aR,5aR,6S,9aS,9bR)-2-(2,5-Dimethoxy-tetrahydro-furan-3-yl)-3a-hydroxymethyl-6,9a-dimethyl-dodecahydro-naphtho[2,1-b]furan-6-carboxylic acid methyl ester
  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：

  methyl 2-(3-furyl)-3a-hydroxymethyl-6,9a-dimethylperhydronaphtho-[2,1-b]furan-6-carboxylate 、 甲醇 在 chloramine-B 、 溶剂黄146 作用下， 反应 0.17h， 以87%的产率得到methyl 3a-hydroxymethyl-2-(2,5-dimethoxy-2,5-dihydrofuran-3-yl)-6,9a-dimethyldodecahydronaphtho[2,1-b]furan-6-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