1,2-diphenyl-5-piperidino-pentan-3-one | 116601-76-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-diphenyl-5-piperidino-pentan-3-one
• 英文别名: 1,2-Diphenyl-5-piperidino-pentan-3-on；1,Phenyl-1-benzyl-4-piperidino-butanon-(2)
• CAS: 116601-76-4
• 化学式: C₂₂H₂₇NO
• 分子量: 321.462
• InChiKey: VLMQRQJVPBDMJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-diphenyl-5-piperidino-pentan-3-one 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 4-nitro-benzoic acid-(1-bibenzyl-α-yl-3-piperidino-propyl ester)
  参考文献：
  名称：

  Ghosh et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 319

  摘要：

  DOI：
• 作为产物：
  描述：

  1t,2-diphenyl-5-piperidino-pent-1-en-3-one; hydrochloride 在 palladium on activated charcoal 、 乙醇 作用下， 生成 1,2-diphenyl-5-piperidino-pentan-3-one
  参考文献：
  名称：

  Ghosh et al., Journal of the Indian Chemical Society, 1959, vol. 36, p. 319

  摘要：

  DOI：

文献信息

• Gamma-hydroxy quaternary ammonium compounds
  申请人：MERCK & CO INC

  公开号：US02665278A1

  公开（公告）日：1954-01-05

  The invention comprises compounds of the formula in which R is an alkyl (having up to 10 carbon atoms), cycloaliphatic, aralkyl or aryl radical, R1 is an alkyl (having up to 10 carbon atoms), aralkyl, allyl or cinnamyl radical, NA is a secondary amine residue and X is an anion. Such compounds are obtained by reacting a g -hydroxy-tertiary amine with a quaternizing agent of the formula R1X in which R1 has the meaning heretofore described and X is for example halide or methylsulphate. A quaternary ammonium bromide or iodide may be converted to the corresponding hydroxide by treatment in aqueous solution with silver oxide. The hydroxide may then be neutralized with another acid, e.g. phosphoric, to give a product with the corresponding radical at X. Anions derived from inorganic acids, carboxylic acids and sulphonic acids are preferred. In an example (1) 1-phenyl-1-isopropyl-4-dimethylamino-2-butanol is converted to 3-hydroxy-5-methyl - 4 - phenylhexyltrimethylammonium iodide. This product is converted to the corresponding quaternary ammonium hydroxide, portions of which are neutralized with phosphoric, acetic, sulphuric, p-toluenesulphonic and benzoic acids respectively. Similarly prepared are (2) 1-(3-hydroxy-5-methyl-4-phenylhexyl) - 1 - methylpiperidinium iodide; (3) 4 - cyclohexyl - 3 - hydroxy - 4 - phenylbutyl - trimethyl - ammonium iodide; (4) 3-hydroxy - 4,5 - diphenylamyltrimethyl - ammonium iodide; (5) 3 - hydroxy - 4 - phenylhexyltrimethylammonium iodide; (6) 1-methyl - 1 - (3 - hydroxy - 4,4 - diphenylbutyl)-piperidinium iodide; (7) 1 - (4,5 - diphenyl - 3-hydroxyamyl) - 1 - methyl - piperidinium iodide; (8) 1 - ethyl - 1 - (3 - hydroxy - 5-methyl - 4 - phenylhexyl) - piperidinium iodide; (9) 1 - benzyl - 1 - (3 - hydroxy - 5 - methyl - 4-phenylhexyl) - piperidinium bromide; (10) 3-hydroxy - 5 - methyl - 4 - phenylhexyltrimethylammonium methylsulphate; (11) 3 - hydroxy4 - phenylheptyltrimethylammonium methylsulphate; (12) 1 - (3 - hydroxy - 5 - methyl - 4-phenylhexyl) - 1 - cinnamylpiperidinium bromide; (13) 1 - (3 - hydroxy - 5 - methyl - 4-phenylhexyl) - 1 - allylpiperidinium bromide. 1 - Isopropyl - 1 - phenyl - 4 - (1 - piperidyl)-2-butanol used as starting material in example (2) is obtained by reduction with a platinum oxide catalyst of 1-isopropyl-1-phenyl-4-(1-piperidyl) - 2 - butanone hydrochloride (prepared by the Mannich reaction from 3-phenyl-4-methyl - 2 - pentanone, paraformaldehyde and piperidine hydrochloride). Specifications 693,128, 722,167 and 733,406 are referred to.

  该发明涉及公式的化合物，其中R是烷基（具有最多10个碳原子）、环烷基、芳基烷基或芳基基团，R1是烷基（具有最多10个碳原子）、芳基烷基、烯丙基或肉桂基团，NA是次级胺残基，X是阴离子。这些化合物是通过将g-羟基-三级胺与公式R1X的季铵化试剂反应得到的，其中R1具有前述的含义，X例如卤化物或甲基磺酸盐。季铵溴化物或碘化物可以通过在水溶液中用氧化银处理来转化为相应的氢氧化物。然后，氢氧化物可以用另一种酸，例如磷酸，中和以得到具有相应基团的产品。优选的阴离子来自无机酸、羧酸和磺酸。例如(1)1-苯基-1-异丙基-4-二甲氨基-2-丁醇被转化为3-羟基-5-甲基-4-苯基己基三甲基铵碘化物。该产品被转化为相应的季铵氢氧化物，其中的部分被分别用磷酸、乙酸、硫酸、对甲苯磺酸和苯甲酸中和。类似地制备了(2)1-(3-羟基-5-甲基-4-苯基己基)-1-甲基哌啶碘化物；(3)4-环己基-3-羟基-4-苯基丁基-三甲基铵碘化物；(4)3-羟基-4,5-二苯基戊基三甲基铵碘化物；(5)3-羟基-4-苯基己基三甲基铵碘化物；(6)1-甲基-1-(3-羟基-4,4-二苯基丁基)-哌啶碘化物；(7)1-(4,5-二苯基-3-羟基戊基)-1-甲基哌啶碘化物；(8)1-乙基-1-(3-羟基-5-甲基-4-苯基己基)-哌啶碘化物；(9)1-苄基-1-(3-羟基-5-甲基-4-苯基己基)-哌啶溴化物；(10)3-羟基-5-甲基-4-苯基己基三甲基铵甲基磺酸盐；(11)3-羟基4-苯基庚基三甲基铵甲基磺酸盐；(12)1-(3-羟基-5-甲基-4-苯基己基)-1-肉桂基哌啶溴化物；(13)1-(3-羟基-5-甲基-4-苯基己基)-1-烯丙基哌啶溴化物。在示例（2）中使用的1-异丙基-1-苯基-4-(1-哌啶基)-2-丁醇是通过用铂氧化物催化还原1-异丙基-1-苯基-4-(1-哌啶基)-2-丁酮盐酸盐（由3-苯基-4-甲基-2-戊酮、多聚甲醛和哌啶盐酸盐的曼尼希反应制备）得到的。参考规范693,128、722,167和733,406。
• Gamma-keto-tertiary amines and derivatives thereof
  申请人：MERCK &

  公开号：US02835676A1

  公开（公告）日：1958-05-20
• DE948969
  申请人：——

  公开号：——

  公开（公告）日：——
• Gamma-acyloxy-tertiary amines
  申请人：MERCK &

  公开号：US02680765A1

  公开（公告）日：1954-06-08