6β-p-toluenesulphonyloxymethyl-19-norcholest-5(10)-en-3β-ol acetate | 62684-22-4

• 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-p-toluenesulphonyloxymethyl-19-norcholest-5(10)-en-3β-ol acetate
• 英文别名: 6β-p-Toluolsulfonyloxymethyl-19-norcholest 5(10)en-3β-ol-acetat；[(3S,6R,8S,9S,13R,14S,17R)-13-methyl-17-[(2R)-6-methylheptan-2-yl]-6-[(4-methylphenyl)sulfonyloxymethyl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 62684-22-4
• 化学式: C₃₆H₅₄O₅S
• 分子量: 598.888
• InChiKey: JERSGYGKUBVLMC-MEWFTGFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.65
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6β-p-toluenesulphonyloxymethyl-19-norcholest-5(10)-en-3β-ol acetate 在 sodium hydroxide 、 lithium bromide 作用下， 以 甲醇 、 异丙醇 为溶剂， 生成 6β-Brommethyl-19-nor-cholest-5(10)-en-3β-ol
  参考文献：
  名称：

  A New Route to 6β-Iodomethyl- and 6β-Bromomethyl-19-norcholest-5(10)-en-3β-ol

  摘要：

  DOI：

  10.1055/s-1977-24265
• 作为产物：
  描述：

  cholest-5-ene-3β,19-diol 3-acetate 19-tosylate 以 乙腈 为溶剂， 生成 6β-p-toluenesulphonyloxymethyl-19-norcholest-5(10)-en-3β-ol acetate
  参考文献：
  名称：

  A New Route to 6β-Iodomethyl- and 6β-Bromomethyl-19-norcholest-5(10)-en-3β-ol

  摘要：

  DOI：

  10.1055/s-1977-24265

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.