(13E)-6β,7α,15-triacetoxy-labda-8,13-diene | 1015763-01-5

• 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: (13E)-6β,7α,15-triacetoxy-labda-8,13-diene
• 英文别名: 6β,7α,15-triacetoxylabda-8,13E-diene；[(E)-5-[(3S,4S,4aS,8aS)-3,4-diacetyloxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl] acetate
• CAS: 1015763-01-5
• 化学式: C₂₆H₄₀O₆
• 分子量: 448.6
• InChiKey: ZCSONGATRIIYBY-WBAUYTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (13E)-labda-8,13-diene-6β,7α,15-triol 、 乙酰氯 在 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以98%的产率得到(13E)-6β,7α,15-triacetoxy-labda-8,13-diene
  参考文献：
  名称：

  Synthetic studies to highly functionalised B ring labdanes

  摘要：

  Several 6,7-dioxygenated (cis or trans) labdanes have been synthesised starting front sclareol. A new strategy that allows the obtention of diols alpha-cis as well as beta-cis of trans is described. In particular, the syntheses of three natural highly functionalised labdanes in the B rings of 2, 3 and 4 with different side chains are reported. The syntheses have permitted to Correct the proposed Structure for one of them. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.083

文献信息

• Bioactive Metabolites from the South African Marine Mollusk <i>Trimusculus costatus</i>
  作者：Albert W. W. van Wyk、Christopher A. Gray、Catherine E. Whibley、Omolaja Osoniyi、Denver T. Hendricks、Mino R. Caira、Michael T. Davies-Coleman

  DOI：10.1021/np070612y

  日期：2008.3.1

  A reinvestigation of extracts of the endemic South African intertidal limpet Trimusculus costatus yielded the known labdane diterpenes 6 beta,7 alpha-diacetoxylabda-8,13E-dien-15-ol (1) and 2 alpha,6 beta,7 alpha-triacetoxylabda-8,13E-dien-15-ol (2) and three new metabolites, 6 beta,7 alpha,15-triacetoxylabda-8,13E-diene (3), 3 alpha,11-dihydroxy-9,11-seco-cholest-4,7-dien-6,9-dione (4), and cholest-7-en-3,5,7-triol (5). Chiral derivatization and X-ray analysis were used to confirm the labdane absolute configuration of 2. Compounds 1, 2 and 4 exhibited moderate activity (3-25 mu M) against the WHCO1 human esophageal cancer cell line.
• Synthetic studies to highly functionalised B ring labdanes
  作者：I.S. Marcos、L. Castañeda、P. Basabe、D. Díez、J.G. Urones

  DOI：10.1016/j.tet.2008.06.083

  日期：2008.9

  Several 6,7-dioxygenated (cis or trans) labdanes have been synthesised starting front sclareol. A new strategy that allows the obtention of diols alpha-cis as well as beta-cis of trans is described. In particular, the syntheses of three natural highly functionalised labdanes in the B rings of 2, 3 and 4 with different side chains are reported. The syntheses have permitted to Correct the proposed Structure for one of them. (C) 2008 Elsevier Ltd. All rights reserved.