Δ¹⁵-Stachen-19-saeure-methylester | 14699-35-5

• 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: Δ¹⁵-Stachen-19-saeure-methylester
• CAS: 14699-35-5
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: QBQDOLZACGWJRX-IQBUSDBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Δ¹⁵-Stachen-19-saeure-methylester 在 palladium on activated charcoal 氢气 作用下， 生成 (10S)-13-methyl-17-nor-phyllocladan-19-oic acid methyl ester
  参考文献：
  名称：

  Structural modifications of isosteviol. Partial synthesis of atiserene and isoatiserene

  摘要：

  DOI：

  10.1021/jo00817a014
• 作为产物：
  描述：

  Isosteviolmethylestertosylhydrazon 生成 Δ¹⁵-Stachen-19-saeure-methylester
  参考文献：
  名称：

  Biogenetic-like rearrangements of tetracyclic diterpenes

  摘要：

  DOI：

  10.1021/jo00823a013

文献信息

• The chemistry of the tetracyclic diterpenoids—V
  作者：J.R. Hanson

  DOI：10.1016/0040-4020(67)85025-7

  日期：1967.1

  Detailed evidence for the interrelationship between monogynol and steviol and the reverse conversion of the stachene skeleton to the kaurene skeleton is presented. The preparation of stach-15-en-2-one is also described.

  提出了有关甘油一丁香酚和甜菊醇之间相互关系以及将斯塔克烯骨架反向转化为贝壳杉烯骨架的详细证据。还描述了stach-15-en-2-one的制备。
• Synthesis of Natural Atisane-Type Diterpenoids by<i>retro</i>-Biomimetic Transformations
  作者：Nicon Ungur、Veaceslav Kulciţki、Olga Chetraru、Marina Grinco、Pavel F. Vlad

  DOI：10.1002/hlca.201200305

  日期：2013.5

  An efficient one step, retro‐biomimetic procedure for the synthesis of natural products having the atisane structure is described (Scheme 2), natural products which are components of medicinal plants and possess relevant biological activity. Their structures were confirmed by chemical transformations and spectral data. The starting materials were the known ent‐kaur‐16‐en‐19‐oic acid (1) and ent‐trachyloban‐19‐oic

  一种有效的一个步骤，复古-biomimetic过程对于具有atisane结构的天然产物的合成被描述（方案2），这是药用植物的部件和具有相关的生物活性的天然产物。通过化学转化和光谱数据证实了它们的结构。起始原料是已知的ent -kaur-16-en-19-oic酸（1）和ent -trchyloban-19-oic酸（2），即从向日葵废料中容易获得的二萜类化合物。
• Gibberellin-like activity of some tetracyclic diterpenoids from Elaeoselinum species and their derivatives
  作者：Nieves Villalobos、Luisa Martín、María J. Macias、Balbino Mancheño、Manuel Grande

  DOI：10.1016/s0031-9422(00)90330-3

  日期：1994.11

  Abstract The growth-regulatory activity of 13 tetracyclic diterpenoids with kaurane, beyerane and atisane skeletons isolated from Elaeoselinum species (Umbelliferae) has been tested in six bioassays and their activities were compared with that shown by gibberellic acid, GA 3 . Seven of the tested substances showed an activity similar or greater than that displayed by GA 3 at concentrations 1 to 10

  摘要 13 种四环二萜类化合物的生长调节活性与从Elaeoselinum 物种（伞形科）分离的贝壳杉烷、拜尔烷和atisane 骨架已在六种生物测定中进行了测试，并将它们的活性与赤霉酸GA 3 显示的活性进行了比较。七种测试物质显示出与GA 3 在1至10 μg ml -1 浓度下显示的活性相似或更高的活性。最活跃的化合物是ent -15α-angeloyloxykaur-16-ene-3β-yl acetate,methyl ent -18-angeloyloxykaur-16-ene-19-oate,methyl ent -beyer-15-ene-19-oate,methyl ent -14pβ-tygloyloxybeyer-15-ene-19-oate (methyl elasclepiate) 和 ent -beyer-15-ene-14β,19-diol。
• High stereoselective semisynthesis of kauroxane and beyeroxane compounds
  作者：Ana K. Villagómez-Guzmán、Laura Hernández-Padilla、Gabriela Rodríguez-García、Carlos J. Cortés-García、Jesús Campos-García、Rosa E. del Río、Christine Thomassigny、Mario A. Gómez-Hurtado

  DOI：10.1016/j.molstruc.2024.137904

  日期：2024.6

  A semisynthetic strategy to access novel kauroxane or beyeroxane compounds from ‑kauranal or ‑beyerenal, respectively, is described. A Prins cyclization was used as a key step reaction to synthesize diterpene-tetrahydropyran hybrid compounds with high stereoselectivity by using 3-buten-1-ol as oxane precursor and indium trichloride as the Lewis acid catalyst. The absolute configurations of new compounds

  描述了一种分别从 ‐kauranal 或 ‐beyerenal 中获取新型贝叶氧烷或贝叶兰化合物的半合成策略。以3-丁烯-1-醇为氧烷前驱体，三氯化铟为Lewis酸催化剂，以Prins环化反应为关键步骤，合成了高立体选择性的二萜-四氢吡喃杂化化合物。新化合物的绝对构型通过机械方法确定，并通过 DFT 计算支持，并考虑与二萜手性纯度及其构象限制相关的立体选择性行为。这些结构通过其物理和光谱数据得以阐明。最后，目标分子的抗增殖活性完成，具有中等的生物活性。