(2-fluoromethylestra-1,3,5(10)-triene-17-one-3-yl)-(2,2,2-trichloroethyl)sulfate | 653605-39-1

• 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: (2-fluoromethylestra-1,3,5(10)-triene-17-one-3-yl)-(2,2,2-trichloroethyl)sulfate
• 英文别名: [(8R,9S,13S,14S)-2-(fluoromethyl)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] 2,2,2-trichloroethyl sulfate
• CAS: 653605-39-1
• 化学式: C₂₁H₂₄Cl₃FO₅S
• 分子量: 513.842
• InChiKey: ACGMRXMKOZJINE-MQJTVSLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2-fluoromethylestra-1,3,5(10)-triene-17-one-3-yl)-(2,2,2-trichloroethyl)sulfate 在 palladium on activated charcoal 、 钯 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以75%的产率得到ammonium (2-fluoromethylestra-1,3,5(10)-triene-17-one-3-yl)sulfate
  参考文献：
  名称：

  Synthesis and Protection of Aryl Sulfates Using the 2,2,2-Trichloroethyl Moiety

  摘要：

  [GRAPHICS]The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield. This approach to aryl sulfate synthesis was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies.

  DOI：

  10.1021/ol036157o
• 作为产物：
  描述：

  2-hydroxymethylestra-1,3,5(10)-triene-17-one-3-yl-(2,2,2-trichloroethyl)sulfate 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(2-fluoromethylestra-1,3,5(10)-triene-17-one-3-yl)-(2,2,2-trichloroethyl)sulfate
  参考文献：
  名称：

  Synthesis and Protection of Aryl Sulfates Using the 2,2,2-Trichloroethyl Moiety

  摘要：

  [GRAPHICS]The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for aryl sulfates. Aryl sulfates, protected with the TCE group, were prepared in high yield by reacting phenols with chlorosulfuric acid TCE ester. Deprotection was accomplished using Pd/C-ammonium formate or with Zn-ammonium formate to give aryl sulfate monoesters in high yield. This approach to aryl sulfate synthesis was successfully applied to the construction of estrone sulfate derivatives, which could not be prepared by previous methodologies.

  DOI：

  10.1021/ol036157o