3-(3,4-二苯基吡唑-1-基)丙腈 | 67455-52-1

• 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-(3,4-二苯基吡唑-1-基)丙腈
• 英文名称: 1-(2-cyanoethyl)-3,4-diphenylpyrazole
• 英文别名: 3-(3,4-diphenyl-pyrazol-1-yl)-propionitrile；1-(2-cyanoethyl)-diphenyl-1H-pyrazole；3-(3,4-Diphenyl-1H-pyrazol-1-yl)propanenitrile；3-(3,4-diphenylpyrazol-1-yl)propanenitrile
• CAS: 67455-52-1
• 化学式: C₁₈H₁₅N₃
• 分子量: 273.337
• InChiKey: PUXUEPFDKXBXMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3,4-二苯基吡唑-1-基)丙腈 在 aluminum nickel 盐酸 、 氨 作用下， 以 甲醇 、 乙醇 、 醋酸异丙酯 、 氢气 、 异丙醇 为溶剂， 生成 1-(3-aminopropyl)-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 以69的产率得到3-(3,4-二苯基吡唑-1-基)丙腈
  参考文献：
  名称：

  J. Med. Chem. 1985, 28, 256-260

  摘要：

  DOI：

文献信息

• 1H-pyrazole-1-alkanamides and preparation useful as antiarrhythmic agents
  申请人：STERLING DRUG INC.

  公开号：EP0299407A1

  公开（公告）日：1989-01-18

  N-[(disubstituted amino)alkyl]-3,4 (or 4,5)-diaryl-­1H-pyrazole-1-acetamides and pyrazole-1-propanamides, useful for treating cardiac arrhythmias in mammals, are prepared by reacting a lower-alkyl ester or pyrazole-1-acetic or propanoic acid with an appropriate diamine or by reacting a lower-alkyl ester of a pyrazole-1-acetic or propanoic acid with an ω-­aminoalkanol, followed by activation of the alcohol and displacement of an appropriate amine.

  N-[(二取代氨基)烷基]-3,4(或 4,5)-二芳基-1H-吡唑-1-乙酰胺和吡唑-1-丙酰胺，可用于治疗哺乳动物的心律失常、其制备方法是将吡唑-1-乙酸或丙酸的低级烷基酯与适当的二胺反应，或将吡唑-1-乙酸或丙酸的低级烷基酯与ω-氨基醇反应，然后使醇活化并置换适当的胺。
• Azole-1-alkanamides as antiarrhytmic agents and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0388690A1

  公开（公告）日：1990-09-26

  N-[(heterocycle)alkyl]3,4-(or 4,5)-diaryl-1H-­pyrazole-1-acetamides and pyrazole-1-propanamides or acid-addition salt thereof wherein R¹ is hydrogen or lower-alkyl; R² and R³ are independently hydrogen, hydroxy, lower-alkyl, lower-alkoxy, lower-alkylamino, lower-alkylamido, lower-alkylsulfonamido, nitro, amino, cyano, or halo; R⁴ is hydrogen or hydroxy; m is one or two; p is one, two, or three; and A is a five-or six membered heterocycle containing carbon, hydrogen and nitrogen and attached to (CH₂)p at a carbon, or A is a five-or six-membered heterocycle, substituted with a lower-alkyl group, containing carbon, hydrogen and nitrogen and attached to (CH₂)p at a carbon, useful for treating cardiac arrhythmias in mammals, are prepared by reacting a lower-alkyl ester of pyrazole-1-acetic or propanoic acid with an appropriate (heterocycle-alkyl) amine or by reacting a pyrazole-1-acetic or propanoic acid with an appropriate (heterocycle-alkyl)amine.

  N-[（杂环）烷基]3,4-（或 4,5）-二芳基-1H-吡唑-1-乙酰胺和吡唑-1-丙酰胺 或其酸加成盐 其中R¹是氢或低级烷基；R²和R³独立地是氢、羟基、低级烷基、低级烷氧基、低级烷基氨基、低级烷基酰胺、低级烷基磺酰胺、硝基、氨基、氰基或卤素；R⁴是氢或羟基；m是1或2；p是1、2或3；且 A 是含碳、氢和氮并在一个碳上与 (CH₂)p 连接的五或六元杂环，或 A 是被低级烷基取代的含碳、氢和氮并在一个碳上与 (CH₂)p 连接的五或六元杂环、通过将吡唑-1-乙酸或丙酸的低级烷基酯与适当的（杂环-烷基）胺反应，或通过将吡唑-1-乙酸或丙酸与适当的（杂环-烷基）胺反应，制备出有助于治疗哺乳动物心律失常的吡唑-1-乙酸或丙酸低级烷基酯。
• 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.
• BAILEY, D. M.;HANSEN, PH. E.;HLAVAC, A. G.;BAIZMAN, E. R.;PEARL, J.;DEFEL+, J. MED. CHEM., 1985, 28, N 2, 256-260
  作者：BAILEY, D. M.、HANSEN, PH. E.、HLAVAC, A. G.、BAIZMAN, E. R.、PEARL, J.、DEFEL+

  DOI：——

  日期：——
• US4182895A
  申请人：——

  公开号：US4182895A

  公开（公告）日：1980-01-08