ethyl (6Z,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate | 357406-32-7

• 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 (6Z,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate
• CAS: 357406-32-7
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: JDITVCKWSUFDMU-KQPRZUBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (6Z,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate 在 copper(l) iodide 、 Pd(AsPh₃)2 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲苯 为溶剂， 生成 (2E,6Z,10E)-3,7,11,15-tetrametyl-2,6,10,14-hexadecatetraen-1-ol
  参考文献：
  名称：

  Synthesis and evaluation of GGPP geometric isomers: divergent substrate specificities of FTase and GGTase I

  摘要：

  A stereocontrolled synthetic route has been used to prepare two of the geometric isomers of all-trans-GGPP. Neither of these isomers is effective substrates for mammalian GGTase I, but 3 is a potent inhibitor of this enzyme (IC50 = 100 nM). Surprisingly, both compounds are effective substrates for mammalian FTase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00292-x
• 作为产物：
  描述：

  1-bromo-3,7,11-trimethyldodeca-2(Z),6(E),10-triene 、 Acetessigsaeure-ethylester 以 四氢呋喃 为溶剂， 以55%的产率得到ethyl (6Z,10E)-7,11,15-trimethyl-3-oxohexadeca-6,10,14-trienoate
  参考文献：
  名称：

  Synthesis and evaluation of GGPP geometric isomers: divergent substrate specificities of FTase and GGTase I

  摘要：

  A stereocontrolled synthetic route has been used to prepare two of the geometric isomers of all-trans-GGPP. Neither of these isomers is effective substrates for mammalian GGTase I, but 3 is a potent inhibitor of this enzyme (IC50 = 100 nM). Surprisingly, both compounds are effective substrates for mammalian FTase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00292-x

文献信息

• Synthesis and evaluation of GGPP geometric isomers: divergent substrate specificities of FTase and GGTase I
  作者：Todd J. Zahn、Jessica Whitney、Carolyn Weinbaum、Richard A. Gibbs

  DOI：10.1016/s0960-894x(01)00292-x

  日期：2001.6

  A stereocontrolled synthetic route has been used to prepare two of the geometric isomers of all-trans-GGPP. Neither of these isomers is effective substrates for mammalian GGTase I, but 3 is a potent inhibitor of this enzyme (IC50 = 100 nM). Surprisingly, both compounds are effective substrates for mammalian FTase. (C) 2001 Elsevier Science Ltd. All rights reserved.