3-(3-甲基哌啶-1-基)-1-苯基丙烷-1-酮 | 6951-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(3-甲基哌啶-1-基)-1-苯基丙烷-1-酮
• 英文名称: 3-(3'-methylpiperidino)-1-phenyl-propan-1-one
• 英文别名: 3-(3-methyl-piperidin-1-yl)-1-phenyl-propan-1-one；Phenyl-β-<3-pipecolino>-ethyl-keton；3-Methylpiperidino-ethylphenylketon；3-(3-Methylpiperidin-1-yl)-1-phenylpropan-1-one
• CAS: 6951-37-7
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: PWJRCBZVIFAULR-UHFFFAOYSA-N

物化性质

• 沸点：
  352.7±25.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-甲基哌啶-1-基)-1-苯基丙烷-1-酮 、 甲基碘化镁 生成 4-(3-methylpiperidin-1-yl)-2-phenylbutan-2-ol
  参考文献：
  名称：

  ANGIOLINI, L.;BIZZARRI, P. C.;SCAPINI, G.;TRAMONTINI, M., TETRAHEDRON, 1981, 37, N 11, 2137-2142

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基哌啶 在 盐酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 14.0h， 生成 3-(3-甲基哌啶-1-基)-1-苯基丙烷-1-酮
  参考文献：
  名称：

  Hypolipidemic effects of α, β, and γ-alkylaminophenone analogs in rodents

  摘要：

  A number of N-substituted beta-alkylaminophenone derivatives including two alpha- and two gamma-alkylaminophenone analogs were synthesized and investigated for hypolipidemic activity in mice at 8 mg/kg/day ip. Most of these analogs were found to be significantly more active than lovastatin and clofibrate. N-Phenylpiperazinopropiophenone 16 was one of the best derivatives, lowering serum cholesterol levels 41% and serum triglyceride levels 48% after 16 days of drug administration in CF1 mice. In Sprague-Dawley rats, N-phenylpiperazinopropiophenone at 8 mg/kg/day orally also demonstrated more potent hypolipidemic activity than clofibrate, gemfibrozil, and lovastatin at their therapeutic dosage. It significantly reduced tissue cholesterol and triglyceride levels in the aorta wall tissue and lowered the cholesterol and triglyceride levels in chylomicron, very low density lipid (VLDL) and low density lipid (LDL) fractions, while it significantly elevated the cholesterol levels in high density lipid (HDL) fraction. This compound also proved to be active in lowering both cholesterol and triglyceride levels in hyperlipidemic mice and rats induced with atherogenic diet. In vitro liver acetyl coenzyme A (CoA) synthetase, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase, acyl CoA cholesterol acyl transferase (ACAT), sn-glycerol-3-phosphate acyltransferase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase activities were significantly inhibited by N-phenylpiperazinopropiophenone from 25 to 100 mu M.

  DOI：

  10.1016/0223-5234(96)80365-5

文献信息

• Stereochemistry of aminocarbonyl compounds—X
  作者：L. Angiolini、P. Costa Bizzarri、G. Scapini、M. Tramontini

  DOI：10.1016/s0040-4020(01)97970-0

  日期：1981.1

  The stereoselectivity of the title reactions due to a hindering amino group in α-asymmetric aminoketones (1 and 2) and to an asymmetric center far away from the reaction center in β-(methylpiperidino)-ketones (11–14) has been studied. The aminoalcohols obtained (3–8 and 15–22) have been separated in most cases and the relative configurations attributed by NMR. Based on diastereomeric ratios, a N-coordinated

  标题反应由于立体选择性阻碍在α-不对称氨基酮（氨基1和2）和一个不对称中心远离反应中心在β-（甲基哌啶） -酮（11 - 14）进行了研究。获得（氨基醇3 - 8和15 - 22）已经在大多数情况下，用NMR归属的相对构型被分离。基于非对映体比率，已经提出了N配位的环状过渡态，并且至少对于β-氨基酮体系上的格氏反应是有效的。