(8R,2E,6E)-8-hydroxy-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]octa-2,6-dienyl acetate | 1207372-48-2

• 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: (8R,2E,6E)-8-hydroxy-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]octa-2,6-dienyl acetate
• 英文别名: [(2E,6E,8R)-8-hydroxy-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-prop-1-en-2-ylcyclohex-3-en-1-yl]octa-2,6-dienyl] acetate
• CAS: 1207372-48-2
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: CPNMHWALKSAZAL-FTLPBAMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8R,2E,6E)-8-hydroxy-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]octa-2,6-dienyl acetate 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 以98%的产率得到(R,2E,6E)-8-[(tert-butyldimethylsilyl)oxy]-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-en-1-yl]octa-2,6-dien-1-yl acetate
  参考文献：
  名称：

  Enantiospecific Synthesis of the Cubitane Skeleton

  摘要：

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.

  DOI：

  10.1021/ol902854t
• 作为产物：
  描述：

  、 右旋香芹酮 在 lithium diisopropyl amide 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到(8R,2E,6E)-8-hydroxy-3,7-dimethyl-8-[(1S,6S)-3-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]octa-2,6-dienyl acetate
  参考文献：
  名称：

  Enantiospecific Synthesis of the Cubitane Skeleton

  摘要：

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.

  DOI：

  10.1021/ol902854t

文献信息

• Enantiospecific Synthesis of a Novel Rearranged Eunicellane Diterpenoid by SmI2-Mediated Cyclization
  作者：Thomas Lindel、Elisabeth Schöttner、Peter Jones

  DOI：10.1055/s-0029-1216990

  日期：2009.12

  rearranged eunicellane skeleton can be obtained in one step by treatment of an α,β-unsaturated diterpenoid with samarium diiodide generated in situ in THF. NOESY­-based structure analysis revealed the presence of an ansa bridge across a twist-boat six-membered ring. diterpenoids - retro-aldol reaction - samarium diiodide - isoeunicellane - NOESY-based analysis

  针对海洋衍生的二萜类化合物的组装，研究了α-香叶基芳烃的合成和环化。将侧链氢化香芹酮与香叶醇衍生的醛进行3-羟烷基化反应可得到二萜烯丙基磷酸酯。已经表明，环氢化的3-羟基烷基酮的逆醛醇缩合令人惊讶地容易，因为优选的构象类似于Zimmerman-Traxler型过渡态。通过用在THF中原位生成的二碘化sa处理α，β-不饱和二萜类化合物，可以一步获得迄今未知的重排的单纤维素骨架。基于NOESY的结构分析显示，横跨扭转船六元环的ansa桥存在。 二萜类化合物-醛醇缩合反应-二碘化sa-异单纤维烷-基于NOESY的分析
• Enantiospecific Synthesis of the Cubitane Skeleton
  作者：Elisabeth Schöttner、Maren Wiechoczek、Peter G. Jones、Thomas Lindel

  DOI：10.1021/ol902854t

  日期：2010.2.19

  The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THE Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.