5-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-1-(2-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester | 710299-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-1-(2-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
• CAS: 710299-11-9
• 化学式: C₃₅H₃₅ClN₂O₃Si
• 分子量: 595.213
• InChiKey: LKVHBIRZZCIRSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.62
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  53.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-1-(2-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester 在 lithium hydroxide 、 1,1,3,3-四甲基-2-(2-氧代吡啶-1(2H)-基)异脲六氟磷酸盐 [HPTU] 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 48.0h， 生成 1-(2-chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide
  参考文献：
  名称：

  Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: a potential PET ligand for CB1 receptors

  摘要：

  Synthesis and in vitro evaluation of [O-methyl-C-11]1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([C-11]-1), a potential imaging agent for CB, receptors using PET is described. 1-(2-Chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30% overall yield. The reaction of alcohol 5 with [C-11]MeOTf at 60degreesC afforded [C-11]-1 with an average radiochemical yield of 14.5% (EOS) and >2000 Ci/mmol specific activity. The radiotracer was found to selectively label CB, receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.034
• 作为产物：
  描述：

  2-氯苯肼盐酸盐 、 草酸二乙酯 、 4-O-(tert-butyldiphenylsilyl)propiophenone 在 lithium hexamethyldisilazane 、 溶剂黄146 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 5-[4-(tert-Butyl-diphenyl-silanyloxy)-phenyl]-1-(2-chloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: a potential PET ligand for CB1 receptors

  摘要：

  Synthesis and in vitro evaluation of [O-methyl-C-11]1-(2-chlorophenyl)-5-(4-methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide ([C-11]-1), a potential imaging agent for CB, receptors using PET is described. 1-(2-Chlorophenyl)-5-(4-hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (5), the precursor for radiolabeling, was synthesized from 4-OTBDPS-propiophenone (2) in five steps with 30% overall yield. The reaction of alcohol 5 with [C-11]MeOTf at 60degreesC afforded [C-11]-1 with an average radiochemical yield of 14.5% (EOS) and >2000 Ci/mmol specific activity. The radiotracer was found to selectively label CB, receptors in slide-mounted sections of postmortem human brain containing prefrontal cortex as demonstrated by in vitro autoradiography using phosphor imaging. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.034