3,4-二苯基-1H-吡唑-1-丙胺 | 94483-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3,4-二苯基-1H-吡唑-1-丙胺
• 英文名称: 3,4-diphenyl-1H-pyrazole-1-propanamine
• 英文别名: 3-(3,4-diphenyl-pyrazol-1-yl)-propylamine；1-(3-aminopropyl)-3,4-diphenyl-1H-pyrazole；3-(3,4-diphenylpyrazol-1-yl)propan-1-amine
• CAS: 94483-87-1
• 化学式: C₁₈H₁₉N₃
• 分子量: 277.369
• InChiKey: MFIVXFCMSOGNCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3,4-二苯基-1H-吡唑-1-丙胺 在 聚合甲醛 作用下， 以 乙醇 为溶剂， 生成 1-[3-(N,N-dimethylamino)propyl]-3,4-diphenyl-1H-pyrazole dihydrochloride
  参考文献：
  名称：

  1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles

  摘要：

  1-氨基-低碳基-3,4-二苯基-1H-吡唑烷，可用作抗抑郁剂和镇痛剂，通过以下方法制备：将一种.omega.[1-(3,4-二苯基-1H-吡唑基)]-低碳酰胺与碱金属铝氢化物还原；在氨、甲基胺、二甲胺或二乙胺存在下，在1-(氰基-低碳基)-3,4-二苯基-1H-吡唑烷的催化剂作用下氢化还原；将1-(对甲苯磺酰氧基-低碳基)-3,4-二苯基-1H-吡唑烷与低碳基胺反应；在酸受体存在下，将3,4-二苯基吡唑与卤代低碳基胺反应；或将1-(3-氨丙基)-3,4-二苯基-1H-吡唑烷与甲醛还原烷基化。

  公开号：

  US04182895A1
• 作为产物：
  描述：

  丙烯腈 、 3,4-二苯基-1H-吡唑 在 镍 氢氧化钾 、 氨 、 氢气 作用下， 生成 3,4-二苯基-1H-吡唑-1-丙胺
  参考文献：
  名称：

  3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants

  摘要：

  A small series of compounds is described in which a narrow SAR has identified N,N-dimethyl-3,4-diphenyl-1H-pyrazole-1-propanamine, 3, as a potential antidepressant with reduced side effects. The isomeric N,N-dimethyl-4,5-diphenyl-1H-pyrazole-1-propanamine was completely inactive in the primary antidepressant screens. Compounds were synthesized by Michael addition of acrylonitrile to diphenylpyrazole followed by reductive alkylation of the resultant diphenylpyrazolepropionitriles. Compound 3 was equipotent with imipramine in standard antidepressant assays in animals but showed no significant anticholinergic action and did not antagonize the antihypertensive effects of clonidine and guanethidine.

  DOI：

  10.1021/jm00380a020

文献信息

• US4182895A
  申请人：——

  公开号：US4182895A

  公开（公告）日：1980-01-08
• 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants
  作者：Denis M. Bailey、Philip E. Hansen、Allan G. Hlavac、Eugene R. Baizman、Jack Pearl、Albert F. DeFelice、Martin E. Feigenson

  DOI：10.1021/jm00380a020

  日期：1985.2

  A small series of compounds is described in which a narrow SAR has identified N,N-dimethyl-3,4-diphenyl-1H-pyrazole-1-propanamine, 3, as a potential antidepressant with reduced side effects. The isomeric N,N-dimethyl-4,5-diphenyl-1H-pyrazole-1-propanamine was completely inactive in the primary antidepressant screens. Compounds were synthesized by Michael addition of acrylonitrile to diphenylpyrazole followed by reductive alkylation of the resultant diphenylpyrazolepropionitriles. Compound 3 was equipotent with imipramine in standard antidepressant assays in animals but showed no significant anticholinergic action and did not antagonize the antihypertensive effects of clonidine and guanethidine.
• 1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles
  申请人：Sterling Drug Inc.

  公开号：US04182895A1

  公开（公告）日：1980-01-08

  1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles, useful as anti-depressants and analgesics, are prepared by reduction with an alkali metal aluminum hydride of an .omega.[1-(3,4-diphenyl-1H-pyrazolyl)]-lower alkanamide; reduction with hydrogen in the presence of ammonia, methylamine, dimethylamine or diethylamine over a catalyst of a 1-(cyano-lower-alkyl)-3,4-diphenyl-1-H-pyrazole; reaction of a 1-(tosyloxy-lower-alkyl)-3,4-diphenyl-1H-pyrazole with a lower-alkylamine; reaction of 3,4-diphenylpyrazole with a halo-lower-alkylamine in the presence of an acid acceptor; or reductive alkylation with formaldehyde of a 1-(3-aminopropyl)-3,4-diphenyl-1H-pyrazole.

  1-氨基-低碳基-3,4-二苯基-1H-吡唑烷，可用作抗抑郁剂和镇痛剂，通过以下方法制备：将一种.omega.[1-(3,4-二苯基-1H-吡唑基)]-低碳酰胺与碱金属铝氢化物还原；在氨、甲基胺、二甲胺或二乙胺存在下，在1-(氰基-低碳基)-3,4-二苯基-1H-吡唑烷的催化剂作用下氢化还原；将1-(对甲苯磺酰氧基-低碳基)-3,4-二苯基-1H-吡唑烷与低碳基胺反应；在酸受体存在下，将3,4-二苯基吡唑与卤代低碳基胺反应；或将1-(3-氨丙基)-3,4-二苯基-1H-吡唑烷与甲醛还原烷基化。