6β-cyanomethyl-19-norcholest-5(10)-en-3β-ol acetate | 84371-32-4

• 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
• 英文名称: 6β-cyanomethyl-19-norcholest-5(10)-en-3β-ol acetate
• CAS: 84371-32-4
• 化学式: C₃₀H₄₇NO₂
• 分子量: 453.709
• InChiKey: GWJPXEBSWMSMQR-HXDXEUPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.85
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6β-cyanomethyl-19-norcholest-5(10)-en-3β-ol acetate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以66%的产率得到6β-carboxymethyl-19-norcholest-5(10)-en-3β-ol
  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
• 作为产物：
  描述：

  氰化钠 、 6β-p-toluenesulphonyloxymethyl-19-norcholest-5(10)-en-3β-ol acetate 以 二甲基亚砜 为溶剂， 反应 3.0h， 以95%的产率得到6β-cyanomethyl-19-norcholest-5(10)-en-3β-ol acetate
  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