4-benzoyl-1-(2-hydroxyethyl)piperidine | 139676-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzoyl-1-(2-hydroxyethyl)piperidine
• 英文别名: (1-(2-Hydroxyethyl)piperidin-4-yl)(phenyl)methanone；[1-(2-hydroxyethyl)piperidin-4-yl]-phenylmethanone
• CAS: 139676-51-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: RYVGVIUHZKUXBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  382.6±32.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzoyl-1-(2-hydroxyethyl)piperidine 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以89%的产率得到(1-(2-chloroethyl)piperidin-4-yl)(phenyl)methanone
  参考文献：
  名称：

  3- [2- [4-(4-Fluorobenzoyl)piperidin- 1-yl]ethyl] -5,6,7,8-tetrahydro-4(3H)-quinazolinones: serotonin 5-HT2A receptor antagonists endowed with potent central action

  摘要：

  A series of 5,6,7,8-tetrahydro-4(3H)-quinazolinones substituted at the 3-position with 4-benzoyl-1-ethylpiperidine, 4-(4-fluorobenzoyl)-1-ethylpiperidine, 4-[bis-(4-fluorophenyl)methylene]-1-ethylpiperidine, or 4-(4-fluorophenyl)-1-propylpiperazine have been prepared and evaluated in binding assays to determine their affinity at serotonin 5-HT2A receptors as well as in a functional test, ie, wet dog shakes (WDS) induced by L-5-hydroxytryptophan (L-5-HTP), a behavioural response which is mediated by stimulation of 5-HT receptors. Among the compounds prepared. 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) and 2-methyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) proved to be the most potent 5-HT,, receptor antagonists. In binding assays, the two compounds displayed similar affinity for 5-HT, receptors in the nanomolar range to ketanserin and ritanserin. In the WDS test, they were even more potent than ketanserin and ritanserin. Compound 10b, which was found to possess the highest potency and duration of action in the WDS test, was chosen for a preliminary evaluation of its ability to inhibit ethanol intake in rats, a response linked to blockade of the central 5-HT2A, receptors. This compound significantly reduced ethanol intake in rats from the first day of treatment. The results of the present study indicate that 10b is a potent centrally acting antagonist at 5-HT2A receptors.

  DOI：

  10.1016/s0223-5234(97)83291-6
• 作为产物：
  描述：

  2-碘乙醇 、 4-苯甲酰基哌啶盐酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以92%的产率得到4-benzoyl-1-(2-hydroxyethyl)piperidine
  参考文献：
  名称：

  3- [2- [4-(4-Fluorobenzoyl)piperidin- 1-yl]ethyl] -5,6,7,8-tetrahydro-4(3H)-quinazolinones: serotonin 5-HT2A receptor antagonists endowed with potent central action

  摘要：

  A series of 5,6,7,8-tetrahydro-4(3H)-quinazolinones substituted at the 3-position with 4-benzoyl-1-ethylpiperidine, 4-(4-fluorobenzoyl)-1-ethylpiperidine, 4-[bis-(4-fluorophenyl)methylene]-1-ethylpiperidine, or 4-(4-fluorophenyl)-1-propylpiperazine have been prepared and evaluated in binding assays to determine their affinity at serotonin 5-HT2A receptors as well as in a functional test, ie, wet dog shakes (WDS) induced by L-5-hydroxytryptophan (L-5-HTP), a behavioural response which is mediated by stimulation of 5-HT receptors. Among the compounds prepared. 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) and 2-methyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-5,6,7,8-tetrahydro-4(3H)-quinazolinone (10b) proved to be the most potent 5-HT,, receptor antagonists. In binding assays, the two compounds displayed similar affinity for 5-HT, receptors in the nanomolar range to ketanserin and ritanserin. In the WDS test, they were even more potent than ketanserin and ritanserin. Compound 10b, which was found to possess the highest potency and duration of action in the WDS test, was chosen for a preliminary evaluation of its ability to inhibit ethanol intake in rats, a response linked to blockade of the central 5-HT2A, receptors. This compound significantly reduced ethanol intake in rats from the first day of treatment. The results of the present study indicate that 10b is a potent centrally acting antagonist at 5-HT2A receptors.

  DOI：

  10.1016/s0223-5234(97)83291-6

文献信息

• Convenient new synthesis of umeclidinium bromide
  作者：Jianhui Gu、Jie Zhang、Xuan Wang、Guoping Wang

  DOI：10.1080/00397911.2017.1348525

  日期：2018.5.3

  ABSTRACT Umeclidinium bromide, a drug used for chronic obstructive pulmonary disease, is synthesized through a new intermediate of phenyl(quinuclidin-4-yl)methanone. This novel method with simple operation flow and cheap reagents, makes it suitable for scale up. The overall four-step process provides umeclidinium bromide in 29% yield and the purity up to 99.83%. The X-ray crystal structure of the drug

  摘要 Umeclidinium bromide 是一种用于慢性阻塞性肺疾病的药物，它是通过一种新的苯基（奎宁环-4-基）甲酮中间体合成的。这种新方法操作流程简单，试剂便宜，适合扩大规模。整个四步过程以 29% 的收率和高达 99.83% 的纯度提供了溴化乌美溴铵。首次报道了药物分子的 X 射线晶体结构。图形概要