Ethyl 3-ethyl-7,11-dimethyldodeca-2(E),6(E),10-trienoate | 61252-19-5

• 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: Ethyl 3-ethyl-7,11-dimethyldodeca-2(E),6(E),10-trienoate
• 英文别名: (2E,6E)-3-ethyl-7,11-dimethyl-dodeca-2,6,10-trienoic acid ethyl ester；3-ethyl-7,11-dimethyl-2,6,10-dodecatrienoic acid, ethyl ester；3-ethyl-7,11-dimethyl-2,6,10-dodecatrienoic acid,ethyl ester；trans,trans-γ'-homofarnesenic acid ethyl ester；ethyl (2E,6E)-3-ethyl-7,11-dimethyldodeca-2,6,10-trienoate
• CAS: 61252-19-5
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: HRLPZNWWCDKGRB-DEGBXGGYSA-N

物化性质

• 沸点：
  367.3±31.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

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：
  0.61
• 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：

  Ethyl 3-ethyl-7,11-dimethyldodeca-2(E),6(E),10-trienoate 在 红铝 作用下， 以 苯 为溶剂， 生成 (2E,6E)-7,11-dimethyl-3-ethyl-2,6,10-dodecatrien-1-ol
  参考文献：
  名称：

  法呢基焦磷酸类似物对角鲨烯合成酶的抑制作用。

  摘要：

  已经合成了以下法尼醇类似物的焦磷酸盐：2-甲基法尼醇；7,11-二甲基-3-乙基-2,6,10-十二碳三烯-1-醇; 3-脱甲基法尼醇; 4-甲基硫代法尼醇; 7,11-二甲基-3-碘-2,6,10-十二碳三烯-1-醇; 7,11-二甲基02-碘-2,6,10-十二碳三烯-1-醇; 7,11-二甲基十二烷基-6,10-dien-2-yn-1-ol; 植醇 3,7,11-三甲基-2-十二烯-1-醇; 3,7,11-三甲基十二烷基-1-醇; 和香叶醇。上述所有化合物中的双键均呈E构型，但植醇除外，后者是2E和2Z异构体的7：3混合物。每种焦磷酸盐通过酵母酶制剂抑制标记的法呢基焦磷酸盐掺入角鲨烯。游离醇和单磷酸盐是惰性的。按抑制强度递减的顺序列出的类似物，通过动力学分析为竞争性或混合抑制剂。没有观察到不可逆的抑制作用。结果表明与酶的结合主要由焦磷酸部分介导，焦磷酸部分由相对非特异性的亲脂性相互作

  DOI：

  10.1021/jm00212a011
• 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， 生成 Ethyl 3-ethyl-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.
• [EN] ENZYME MEDIATED PROCESS<br/>[FR] PROCESSUS À MÉDIATION PAR UNE ENZYME
  申请人：GIVAUDAN SA

  公开号：WO2021110858A1

  公开（公告）日：2021-06-10

  An enzyme-mediated method for the production of 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan, the products of said method, and uses of said products.