methyl 15,16-bis[(E)-styryl]-15,16-epoxy-8(9),13(16),14-labdatrien-18-oate | 1311993-12-0

• 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 15,16-bis[(E)-styryl]-15,16-epoxy-8(9),13(16),14-labdatrien-18-oate
• 英文别名: methyl (1S,4aS,8aR)-5-(2-{2,5-bis[(E)-styryl]-furan-3-yl}ethyl)-1,4a,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene-1-carboxylate；methyl (1S,4aS,8aR)-5-[2-[2,5-bis[(E)-2-phenylethenyl]furan-3-yl]ethyl]-1,4a,6-trimethyl-2,3,4,7,8,8a-hexahydronaphthalene-1-carboxylate
• CAS: 1311993-12-0
• 化学式: C₃₇H₄₂O₃
• 分子量: 534.739
• InChiKey: QVUBQRPWJXDELD-GOLRWBJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 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 、 丙酸 、 对苯醌 作用下， 以 乙醚 为溶剂， 反应 10.0h， 以63%的产率得到methyl 15,16-bis[(E)-styryl]-15,16-epoxy-8(9),13(16),14-labdatrien-18-oate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXV. Cross coupling of phlomisoic acid methyl ester with alkenes in the presence of oxidants

  摘要：

  The reaction of phlomisoic acid methyl ester with styrene, catalyzed by Pd(OAc)(2), in the presence of Cu(OAc)(2) and 1,4-benzoquinone in a mixture of propionic acid with diethyl ether gave the corresponding 15,16-distyryl derivative and only traces of 15- and 16-monosubstituted furanolabdanoids. Oxidative coupling of the title compound with methyl acrylate under analogous conditions afforded a mixture of 15-mono-, 16-mono-, and 15,16-dialkenylation products whose ratio changed during the process. The reaction was stereoselective, and the exocyclic double bond in the products had exclusively E configuration.

  DOI：

  10.1134/s107042801104021x

文献信息

• Synthetic transformations of higher terpenoids: XXXII. Synthesis of 16-alkenyl-substituted labdatrienes by oxidative coupling of methyl phlomisoate with alkenes
  作者：Yu. V. Kharitonov、O. I. Kremenko、E. E. Shults、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1134/s1070428013110225

  日期：2013.11

  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.