didehydrofarnesol | 709027-27-0

• 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: didehydrofarnesol
• 英文别名: 3,7,11-trimethyl-dodeca-2,4,6,8,10-pentaen-1-ol；Farnesinol；(2E,4E,6E,8E)-3,7,11-trimethyldodeca-2,4,6,8,10-pentaen-1-ol
• CAS: 709027-27-0
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: XOKHQCCKAMDRCN-BZCYSDSTSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  353.3±11.0 °C(Predicted)
• 密度：
  0.905±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  didehydrofarnesol 在 四丁基磷酸氢铵 作用下， 以 乙腈 为溶剂， 生成 (2E,4E,6E,8E)-3,7,11-trimethyldodeca-2,4,6,8,10-pentaenyl trihydrogen diphosphate
  参考文献：
  名称：

  Didehydrofarnesyl diphosphate: an intrinsically fluorescent inhibitor of protein farnesyltransferase

  摘要：

  Didehydrofarnesyl diphosphate (DeltaDeltaFPP), a fluorescent pentaene analogue of farnesyl diphosphate (FPP), was synthesized using stereoselective Wittig reactions. Although DeltaDeltaFPP was not an alternative substrate for yeast protein farnesyltransferase (FTase), the fluorescent analogue was a potent competitive inhibitor with a K-i value of 8.8 muM (K-m (FPP) = 27 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.077
• 作为产物：
  描述：

  methyl (E)-4-(diethoxyphosphoryl)-2-methylbut-2-enoate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 四丁基氟化铵 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 didehydrofarnesol
  参考文献：
  名称：

  Didehydrofarnesyl diphosphate: an intrinsically fluorescent inhibitor of protein farnesyltransferase

  摘要：

  Didehydrofarnesyl diphosphate (DeltaDeltaFPP), a fluorescent pentaene analogue of farnesyl diphosphate (FPP), was synthesized using stereoselective Wittig reactions. Although DeltaDeltaFPP was not an alternative substrate for yeast protein farnesyltransferase (FTase), the fluorescent analogue was a potent competitive inhibitor with a K-i value of 8.8 muM (K-m (FPP) = 27 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.077

文献信息

• Fischer; Hultzsch, Chemische Berichte, 1935, vol. 68, p. 1732
  作者：Fischer、Hultzsch

  DOI：——

  日期：——
• Fischer; Schulze, Chemische Berichte, 1942, vol. 75, p. 1469
  作者：Fischer、Schulze

  DOI：——

  日期：——
• Didehydrofarnesyl diphosphate: an intrinsically fluorescent inhibitor of protein farnesyltransferase
  作者：Xiao-hui Liu、Glenn D. Prestwich

  DOI：10.1016/j.bmcl.2004.02.077

  日期：2004.5

  Didehydrofarnesyl diphosphate (DeltaDeltaFPP), a fluorescent pentaene analogue of farnesyl diphosphate (FPP), was synthesized using stereoselective Wittig reactions. Although DeltaDeltaFPP was not an alternative substrate for yeast protein farnesyltransferase (FTase), the fluorescent analogue was a potent competitive inhibitor with a K-i value of 8.8 muM (K-m (FPP) = 27 muM). (C) 2004 Elsevier Ltd. All rights reserved.