labda-8(17),13(E)-dien-15-yl benzoate | 142720-57-8

• 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: labda-8(17),13(E)-dien-15-yl benzoate
• 英文别名: Labda-8(17),13E-dien-15-ol benzoate；[(E)-5-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl] benzoate
• CAS: 142720-57-8
• 化学式: C₂₇H₃₈O₂
• 分子量: 394.598
• InChiKey: GAAWFFVQYCMJDB-VAVFEAENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  labda-8(17),13(E)-dien-15-yl benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到2-戊烯-1-醇,5-[(1S,4aS,8aS)-十氢-5,5,8a-三甲基-2-亚甲基-1-萘基]-3-甲基-,(2E)-
  参考文献：
  名称：

  Total synthesis of (+)-9,10-syn- and (+)-9,10-anti-copalol via epoxy trienylsilane cyclizations.

  摘要：

  Total syntheses of (+)-9,10-syn-copalol (5), the pyrophosphate ester of which is a likely intermediate in the biosynthesis of 9,10-syn diterpenes, and its 9,10-anti isomer 39 are reported. Lithiation of (-)-(6R)-6,7-epoxygeranyl p-tolylsulfone (-)-19 or (+/-)-19 followed by alkylation with (E,Z)- and (E,E)-8-bromo-9-(trimethylsilyl)geranyl benzyl ethers (15a and 15b) and selective reductive cleavage of the toluenesulfonyl and benzyl groups afforded (2E,6E,10E,14R)- and (2E,6Z,10E,14R)-14,15-epoxy-19-(trimethylsilyl)geranylgeraniols ((-)-24a and (+/-)-26a). Lewis acid treatment of the benzoate and/or acetates of (-)-24a and (+/-)-26a effected efficient but almost stereorandom bicyclizations to 9,10-syn- and 9,10-anti-labda-8(17),13(E)-diene-3-beta,15-diol esters (27a,b and 28a,b) which were converted to (+)-9,10-syn- and (+)-9,10-anti-copalol.

  DOI：

  10.1021/jo00043a014
• 作为产物：
  描述：

  (+)-3-oxolabda-8(17),13(E)-dien-15-yl benzoate 在 四丁基醋酸铵 、 儿萘酚硼烷 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 labda-8(17),13(E)-dien-15-yl benzoate
  参考文献：
  名称：

  Total synthesis of (+)-9,10-syn- and (+)-9,10-anti-copalol via epoxy trienylsilane cyclizations.

  摘要：

  Total syntheses of (+)-9,10-syn-copalol (5), the pyrophosphate ester of which is a likely intermediate in the biosynthesis of 9,10-syn diterpenes, and its 9,10-anti isomer 39 are reported. Lithiation of (-)-(6R)-6,7-epoxygeranyl p-tolylsulfone (-)-19 or (+/-)-19 followed by alkylation with (E,Z)- and (E,E)-8-bromo-9-(trimethylsilyl)geranyl benzyl ethers (15a and 15b) and selective reductive cleavage of the toluenesulfonyl and benzyl groups afforded (2E,6E,10E,14R)- and (2E,6Z,10E,14R)-14,15-epoxy-19-(trimethylsilyl)geranylgeraniols ((-)-24a and (+/-)-26a). Lewis acid treatment of the benzoate and/or acetates of (-)-24a and (+/-)-26a effected efficient but almost stereorandom bicyclizations to 9,10-syn- and 9,10-anti-labda-8(17),13(E)-diene-3-beta,15-diol esters (27a,b and 28a,b) which were converted to (+)-9,10-syn- and (+)-9,10-anti-copalol.

  DOI：

  10.1021/jo00043a014

文献信息

• Total synthesis of (+)-9,10-syn- and (+)-9,10-anti-copalol via epoxy trienylsilane cyclizations.
  作者：Nathan K. N. Yee、Robert M. Coates

  DOI：10.1021/jo00043a014

  日期：1992.8

  Total syntheses of (+)-9,10-syn-copalol (5), the pyrophosphate ester of which is a likely intermediate in the biosynthesis of 9,10-syn diterpenes, and its 9,10-anti isomer 39 are reported. Lithiation of (-)-(6R)-6,7-epoxygeranyl p-tolylsulfone (-)-19 or (+/-)-19 followed by alkylation with (E,Z)- and (E,E)-8-bromo-9-(trimethylsilyl)geranyl benzyl ethers (15a and 15b) and selective reductive cleavage of the toluenesulfonyl and benzyl groups afforded (2E,6E,10E,14R)- and (2E,6Z,10E,14R)-14,15-epoxy-19-(trimethylsilyl)geranylgeraniols ((-)-24a and (+/-)-26a). Lewis acid treatment of the benzoate and/or acetates of (-)-24a and (+/-)-26a effected efficient but almost stereorandom bicyclizations to 9,10-syn- and 9,10-anti-labda-8(17),13(E)-diene-3-beta,15-diol esters (27a,b and 28a,b) which were converted to (+)-9,10-syn- and (+)-9,10-anti-copalol.