Ethyl 3-vinyl-7,11-dimethyldodeca-2(E),6(E),10-trienoate

• 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: Ethyl 3-vinyl-7,11-dimethyldodeca-2(E),6(E),10-trienoate
• 英文别名: ethyl (2E,6E)-3-ethenyl-7,11-dimethyldodeca-2,6,10-trienoate
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: AWKBVLGNXSYBCT-KWOQVVRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl acetoacetate sodium salt 在 copper(l) iodide 、 正丁基锂 、 Pd(AsPh₃)2 、 双(三甲基硅烷基)氨基钾 作用下， 以 various solvent(s) 为溶剂， 反应 15.0h， 生成 Ethyl 3-vinyl-7,11-dimethyldodeca-2(E),6(E),10-trienoate
  参考文献：
  名称：

  A Pd(0)-catalyzed route to 13-methylidenefarnesyl diphosphate

  摘要：

  The synthesis of the novel FPP analog 13-methylidenefarnesyl diphosphate 2 is described. The key step in the synthetic sequence involved the stereoselective coupling of enol triflate 8 with vinyltributyltin using Pd(AsPh(3))(2) and CuI as catalysts to afford primarily the desired cis-divinylester 7. It is also demonstrated that other 3-substituted famesyl analogs can be prepared by this Pd(0)catalyzed route.

  DOI：

  10.1016/s0040-4039(00)77157-7

文献信息

• A Stereoselective Palladium/Copper-Catalyzed Route to Isoprenoids: Synthesis and Biological Evaluation of 13-Methylidenefarnesyl Diphosphate
  作者：Richard A. Gibbs、Usha Krishnan、Julia M. Dolence、C. Dale Poulter

  DOI：10.1021/jo00129a023

  日期：1995.12

  The novel farnesyl diphosphate (FPP) analog 13-methylidenefarnesyl diphosphate (3-VFPP, 4) was designed as a potential mechanism-based inhibitor of the FPP-utilizing enzyme protein-farnesyl transferase (PFTase). A six-step stereoselective route to 3-VFPP is described. The key step in the synthetic sequence involved the stereoselective coupling of vinyl triflate 16 with vinyltributyltin using Pd(AsPh(3))(2) and CuI as catalysts to afford primarily the desired (Z)-divinyl ester 15. It was also demonstrated that other 3-substituted farnesyl analogs can be prepared in a highly stereoselective manner by this Pd(0)/CuI-catalyzed route. The presence of CuI significantly increases the stereoselectivity of the coupling reaction, and a possible mechanistic rationale for this observation is presented. Biological evaluation of 3-VFPP demonstrates that it is not a time-dependent inhibitor of recombinant yeast PFTase. Instead, 3-VFPP is an alternative substrate for this. enzyme that exhibits a K-m comparable to FPP but a k(cat) significantly lower than the natural substrate.
• A Pd(0)-catalyzed route to 13-methylidenefarnesyl diphosphate
  作者：Richard A. Gibbs、Usha Krishnan

  DOI：10.1016/s0040-4039(00)77157-7

  日期：1994.4

  The synthesis of the novel FPP analog 13-methylidenefarnesyl diphosphate 2 is described. The key step in the synthetic sequence involved the stereoselective coupling of enol triflate 8 with vinyltributyltin using Pd(AsPh(3))(2) and CuI as catalysts to afford primarily the desired cis-divinylester 7. It is also demonstrated that other 3-substituted famesyl analogs can be prepared by this Pd(0)catalyzed route.