1-(2-fluoroethyl)-2-(trifluoromethanesulfonyloxy)benzene | 658704-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-fluoroethyl)-2-(trifluoromethanesulfonyloxy)benzene
• 英文别名: [2-(2-Fluoroethyl)phenyl] trifluoromethanesulfonate
• CAS: 658704-36-0
• 化学式: C₉H₈F₄O₃S
• 分子量: 272.22
• InChiKey: HXUJQFYSTXVPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-fluoroethyl)-2-(trifluoromethanesulfonyloxy)benzene 、 6-(tert-butyldiphenylsilyloxy)-3-[4-(2-(piperidin-1-yl)ethoxy)benzoyl]-2-tributylstannylbenzo[b]thiophene 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 {6-(tert-Butyl-diphenyl-silanyloxy)-2-[2-(2-fluoro-ethyl)-phenyl]-benzo[b]thiophen-3-yl}-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
  参考文献：
  名称：

  Synthesis and binding affinities of fluoroalkylated raloxifenes

  摘要：

  Three fluoroalkylated derivatives (1-3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C-C bond formation of benzo[b]thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substituted raloxifenes 1-3 are 45, 60, 89%, respectively, relative to the affinity of estradiol, which is higher than the affinity of raloxifene itself (25%). When labeled with the positron-emitting radio-nuclide, these compounds might be useful as PET imaging agents for estrogen receptor-positive breast tumors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00362-6
• 作为产物：
  描述：

  邻羟基苯乙醇 在 2,6-二甲基吡啶 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-(2-fluoroethyl)-2-(trifluoromethanesulfonyloxy)benzene
  参考文献：
  名称：

  Synthesis and binding affinities of fluoroalkylated raloxifenes

  摘要：

  Three fluoroalkylated derivatives (1-3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C-C bond formation of benzo[b]thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substituted raloxifenes 1-3 are 45, 60, 89%, respectively, relative to the affinity of estradiol, which is higher than the affinity of raloxifene itself (25%). When labeled with the positron-emitting radio-nuclide, these compounds might be useful as PET imaging agents for estrogen receptor-positive breast tumors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00362-6