1-<1-(ethoxycarbonyl)-4-piperidinyl>-5-tert-butylbenzimidazolone | 107618-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-<1-(ethoxycarbonyl)-4-piperidinyl>-5-tert-butylbenzimidazolone
• 英文别名: 1-[1-(ethoxycarbonyl)-4-piperidinyl]-5-tert-butylbenzimidazolone；ethyl 4-(5-tert-butyl-2-oxo-3H-benzimidazol-1-yl)piperidine-1-carboxylate
• CAS: 107618-29-1
• 化学式: C₁₉H₂₇N₃O₃
• 分子量: 345.442
• InChiKey: PBPMRPLGOSIAAW-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 密度：
  1.174±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-<1-(ethoxycarbonyl)-4-piperidinyl>-5-tert-butylbenzimidazolone 在 sodium hydroxide 作用下， 反应 8.0h， 以83.2%的产率得到1-(4-piperidinyl)-5-tert-butylbenzimidazolone
  参考文献：
  名称：

  Synthesis and neuroleptic activity of a series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimidazolone derivatives

  摘要：

  A series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimid azolones with various substituents in both aromatic rings have been synthesized and tested for neuroleptic activity (antiapomorphine effects and [3H]spiroperidol binding) as well as extrapyramidal effects (cataleptogenic effect). A strong dependence of activity on the 5-substituent in the benzimidazolone moiety could be demonstrated. Some compounds show a large split between the desired antiapomorphine and the undesired extrapyramidal effect. From these, 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]-5-chlor obenzimidazol-2-one hydrochloride (HR 723), 12, has been selected for further preclinical and toxicological profiling.

  DOI：

  10.1021/jm00388a012
• 作为产物：
  描述：

  4-氨基-1-哌啶甲酸乙酯 在 镍 氢气 、 sodium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 160.0 ℃ 、120.0 kPa 条件下， 反应 29.5h， 生成 1-<1-(ethoxycarbonyl)-4-piperidinyl>-5-tert-butylbenzimidazolone
  参考文献：
  名称：

  Synthesis and neuroleptic activity of a series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimidazolone derivatives

  摘要：

  A series of 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]benzimid azolones with various substituents in both aromatic rings have been synthesized and tested for neuroleptic activity (antiapomorphine effects and [3H]spiroperidol binding) as well as extrapyramidal effects (cataleptogenic effect). A strong dependence of activity on the 5-substituent in the benzimidazolone moiety could be demonstrated. Some compounds show a large split between the desired antiapomorphine and the undesired extrapyramidal effect. From these, 1-[1-(benzo-1,4-dioxan-2-ylmethyl)-4-piperidinyl]-5-chlor obenzimidazol-2-one hydrochloride (HR 723), 12, has been selected for further preclinical and toxicological profiling.

  DOI：

  10.1021/jm00388a012

文献信息

• HENNING R.; LATTRELL R.; GARHARDS H. J.; LEVEN M., J. MED. CHEM., 30,(1987) N 5, 814-819
  作者：HENNING R.、 LATTRELL R.、 GARHARDS H. J.、 LEVEN M.

  DOI：——

  日期：——