3-[3,5-bis(trifluoromethyl)phenyl]-1-[1-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl]piperidin-4-yl]imidazolidine-2,4-dione | 960312-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-[3,5-bis(trifluoromethyl)phenyl]-1-[1-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl]piperidin-4-yl]imidazolidine-2,4-dione
• CAS: 960312-51-0
• 化学式: C₂₆H₂₉F₆N₃O₂
• 分子量: 529.526
• InChiKey: BEPBXYAZDKQJHP-KKSFZXQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-[3,5-bis(trifluoromethyl)phenyl]-1-[1-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl]piperidin-4-yl]imidazolidine-2,4-dione 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以45%的产率得到1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-yl)imidazolidin-2-one
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 2: Identification of 2-amino(4-piperidinyl)azoles as potent CXCR3 antagonists

  摘要：

  Development of a lead series of piperidinylurea CXCR3 antagonists has led to the identification of molecules with alternative linkages which retain good potency. A novel 5-(piperidin-4-yl)amino-1,2,4-thiadiazole derivative was found to have satisfactory in vitro metabolic stability and to be orally bioavailable in mice, giving high plasma concentrations and a half life of 5.4 h. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.029
• 作为产物：
  描述：

  methyl (1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-yl)glycinate 、 3,5-双(三氟甲基)苯基异氰酸酯 以 二氯甲烷 为溶剂， 以70%的产率得到3-[3,5-bis(trifluoromethyl)phenyl]-1-[1-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl]piperidin-4-yl]imidazolidine-2,4-dione
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 2: Identification of 2-amino(4-piperidinyl)azoles as potent CXCR3 antagonists

  摘要：

  Development of a lead series of piperidinylurea CXCR3 antagonists has led to the identification of molecules with alternative linkages which retain good potency. A novel 5-(piperidin-4-yl)amino-1,2,4-thiadiazole derivative was found to have satisfactory in vitro metabolic stability and to be orally bioavailable in mice, giving high plasma concentrations and a half life of 5.4 h. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.029