2-(己基桥氧基)-1-甲基丙基十一烷酸酯 | 84371-40-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 2-(己基桥氧基)-1-甲基丙基十一烷酸酯
• 英文名称: 6β-(2'-fluoro)ethyl-19-norcholest-5(10)-en-3β-ol
• 英文别名: 6-Fenco；(3S,6S,8S,9S,13R,14S,17R)-6-(2-fluoroethyl)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 84371-40-4
• 化学式: C₂₈H₄₇FO
• 分子量: 418.679
• InChiKey: ZOZGTABWUGJDJB-CVJVVXCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6β-(2'-hydroxy)ethyl-19-norcholest-5(10)-en-3β-ol diacetate 在 sodium hydroxide 、 甲基三苯氧基碘磷 、 silver fluoride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 30.5h， 生成 2-(己基桥氧基)-1-甲基丙基十一烷酸酯
  参考文献：
  名称：

  Fluoro norcholesterol analogues. Synthesis of 6β-(2'-fluoro)ethyl-19-norcholest-5(10)-EN-3β-OL

  摘要：

  A synthetic route for labelling 6 beta-(2'-fluoro)ethyl-19-norcholest-5(10)-en-3 beta-ol (VII) with fluorine-18 was developed to evaluate the potential utility of VII as an adrenal imaging agent. 6 beta-p-Toluene-sulphonyloxymethyl-19-norcholest-5(10)-en-3 beta-ol acetate (I) was converted to the 6 beta-(2'-hydroxy)ethyl (VI) in a five-step process. The treatment of VI with N-N-diethyl (2-chloro-1,1,2,-trifluoroethyl)amine in methylene chloride and subsequent hydrolysis with base gave the required VII. Iodination of VI with triphenoxymethylphosphonium iodide followed by alkaline hydrolysis gave the 6 beta-(2'-iodo)ethyl (IX) which, on treatment with silver fluoride in acetonitrile, furnished the 6 beta-(2'-fluoro)ethyl (VII). Excellent conversion of the 6-beta-(2'-p-toluenesulphonyloxy)-ethyl (X) into VII was also achieved by heating with potassium fluoride for 2 hr in diethylene glycol in 76% yield, which is a readily applicable method for labelling with fluorine-18.

  DOI：

  10.1016/0039-128x(82)90058-7

文献信息

• Fluoro norcholesterol analogues. Synthesis of 6β-(2'-fluoro)ethyl-19-norcholest-5(10)-EN-3β-OL
  作者：Toshio Kobayashi、Minoru Maeda、Terushi Haradahira、Masaharu Kojima

  DOI：10.1016/0039-128x(82)90058-7

  日期：1982.5

  A synthetic route for labelling 6 beta-(2'-fluoro)ethyl-19-norcholest-5(10)-en-3 beta-ol (VII) with fluorine-18 was developed to evaluate the potential utility of VII as an adrenal imaging agent. 6 beta-p-Toluene-sulphonyloxymethyl-19-norcholest-5(10)-en-3 beta-ol acetate (I) was converted to the 6 beta-(2'-hydroxy)ethyl (VI) in a five-step process. The treatment of VI with N-N-diethyl (2-chloro-1,1,2,-trifluoroethyl)amine in methylene chloride and subsequent hydrolysis with base gave the required VII. Iodination of VI with triphenoxymethylphosphonium iodide followed by alkaline hydrolysis gave the 6 beta-(2'-iodo)ethyl (IX) which, on treatment with silver fluoride in acetonitrile, furnished the 6 beta-(2'-fluoro)ethyl (VII). Excellent conversion of the 6-beta-(2'-p-toluenesulphonyloxy)-ethyl (X) into VII was also achieved by heating with potassium fluoride for 2 hr in diethylene glycol in 76% yield, which is a readily applicable method for labelling with fluorine-18.