β-(3,5-Dimethylpyrazol-1-yl)-propiophenon | 93045-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-(3,5-Dimethylpyrazol-1-yl)-propiophenon
• 英文别名: 3-(3,5-dimethyl-1H-1-pyrazolyl)propiophenone；3-(3,5-dimethyl-pyrazol-1-yl)-1-phenyl-propan-1-one；3-(3,5-Dimethylpyrazol-1-yl)-1-phenylpropan-1-one
• CAS: 93045-21-7
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: OFUXETNGNSRQHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 β-(3,5-Dimethylpyrazol-1-yl)-propiophenon 反应 10.0h， 以98%的产率得到(E)-3-dimethylamino-2-(3,5-dimethyl-1H-1-pyrazolylmethyl)-1-phenyl-2-propen-1-one
  参考文献：
  名称：

  Highly regioselective synthesis of novel 1,4'-bipyrazoles

  摘要：

  Novel 1,4'-bipyrazoles were synthesized via highly regioselective cyclocondensation reactions of b-dimethylaminoenones with hydrazine monohydrate, tert-butylhydrazine hydrochloride, phenylhydrazine hydrochloride or carboxymethylhydrazine. X-ray diffraction technique was used in the elucidation of the regiochemistry of the beta-dimethylaminoenaminones and of the 1,4'-bipyrazoles. 1,4'-Bipyrazolylisoxazoles were also reported.

  DOI：

  10.1590/s0103-50532010000200008
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 3-溴苯丙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以75%的产率得到β-(3,5-Dimethylpyrazol-1-yl)-propiophenon
  参考文献：
  名称：

  Highly regioselective synthesis of novel 1,4'-bipyrazoles

  摘要：

  Novel 1,4'-bipyrazoles were synthesized via highly regioselective cyclocondensation reactions of b-dimethylaminoenones with hydrazine monohydrate, tert-butylhydrazine hydrochloride, phenylhydrazine hydrochloride or carboxymethylhydrazine. X-ray diffraction technique was used in the elucidation of the regiochemistry of the beta-dimethylaminoenaminones and of the 1,4'-bipyrazoles. 1,4'-Bipyrazolylisoxazoles were also reported.

  DOI：

  10.1590/s0103-50532010000200008

文献信息

• Ag2CO3 catalyzed aza-michael addition of pyrazoles to α, β-unsaturated carbonyl compounds: A new access to N-alkylated pyrazole derivatives
  作者：Xue Zhang、Dong-xue Qiu、Wen-ting Qiu、He-ran Wang、Zu-wei Zhao、Hai-feng Yu、Guang-bo Che

  DOI：10.1016/j.tet.2023.133305

  日期：2023.3

  catalyzed aza-Michael addition of pyrazoles to α, β-unsaturated carbonyl compounds is developed. In the present of 5 mol% of Ag2CO3, the reaction smoothly occurs in DCE at 120 °C to afford a series of N-alkylated pyrazoles in good to excellent yields. It is noteworthy that N1-alkylated pyrazoles are obtained with high regioselectivity (N1/N2 up to above 25:1) when asymmetrically substituted pyrazoles reacted

  开发了一种有效的 Ag 2 CO 3催化吡唑氮杂迈克尔加成 α, β-不饱和羰基化合物。在 5 mol% 的 Ag 2 CO 3存在下，反应在 DCE 中在 120 °C 下顺利发生，以良好至优异的产率提供一系列N-烷基化吡唑。值得注意的是，当不对称取代的吡唑与α，β-不饱和羰基化合物反应时， N 1 -烷基化的吡唑具有高区域选择性（N 1 /N 2高达25:1以上）。该方法还可以扩展到克级。
• Highly regioselective synthesis of novel 1,4'-bipyrazoles
  作者：Marcos A. P. Martins、Gabriela F. Fiss、Clarissa P. Frizzo、Fernanda A. Rosa、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1590/s0103-50532010000200008

  日期：——

  Novel 1,4'-bipyrazoles were synthesized via highly regioselective cyclocondensation reactions of b-dimethylaminoenones with hydrazine monohydrate, tert-butylhydrazine hydrochloride, phenylhydrazine hydrochloride or carboxymethylhydrazine. X-ray diffraction technique was used in the elucidation of the regiochemistry of the beta-dimethylaminoenaminones and of the 1,4'-bipyrazoles. 1,4'-Bipyrazolylisoxazoles were also reported.