methyl (1S,4aS,8aR)-5-{2-[2-(1-phenylvinyl)furan-3-yl]ethyl}-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate | 1515848-24-4

• 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 (1S,4aS,8aR)-5-{2-[2-(1-phenylvinyl)furan-3-yl]ethyl}-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate
• 英文别名: 16-(1-phenylvinyl)-15,16-epoxy-8(9),13(16),14-labdatrien-18-oic acid methyl ester；Methyl (1s,4as,8ar)-5-{2-[2-(1-phenylvinyl) furan-3-yl]ethyl}-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate；methyl (1S,4aS,8aR)-1,4a,6-trimethyl-5-[2-[2-(1-phenylethenyl)furan-3-yl]ethyl]-2,3,4,7,8,8a-hexahydronaphthalene-1-carboxylate
• CAS: 1515848-24-4
• 化学式: C₂₉H₃₆O₃
• 分子量: 432.603
• InChiKey: GDYJWXGJWYEJLQ-ZJGIAAPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙烯 、 phlomisoic acid methyl ester 在 氧气 、 copper diacetate 、 palladium diacetate 、 对苯醌 作用下， 以 丙酸 、 乙腈 为溶剂， 反应 10.0h， 以18%的产率得到methyl (1S,4aS,8aR)-5-{2-[2-(1-phenylvinyl)furan-3-yl]ethyl}-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXXII. Synthesis of 16-alkenyl-substituted labdatrienes by oxidative coupling of methyl phlomisoate with alkenes

  摘要：

  Reactions of methyl phlomisoate with methyl acrylate, phenyl acrylate, methyl vinyl ketone, phenyl vinyl ketone, or N-substituted acrylamides catalyzed by Pd(OAc)(2) in the presence of Cu(OAc)(2), p-benzoquinone in the mixture of propionic acid and acetonitrile proceed regio- and stereoselectively with the formation of (E)-16-vinyl labdatrienoates. The oxidative coupling under these conditions of the methyl phlomisoate with styrene results in a mixture of 15,16-distyryl-, 16-styryl-, and 16-(1-phenylvinyl)-derivatives of furanolabdanoid.

  DOI：

  10.1134/s1070428013110225