(E)-1-(pyrazol-1-yl)-4,4,4-trifluoro-2-buten-1-one | 1423809-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1-(pyrazol-1-yl)-4,4,4-trifluoro-2-buten-1-one
• 英文别名: (E)-4,4,4-trifluoro-1-pyrazol-1-ylbut-2-en-1-one
• CAS: 1423809-74-8
• 化学式: C₇H₅F₃N₂O
• 分子量: 190.125
• InChiKey: INUGKGVSTLUSNB-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 (E)-1-(pyrazol-1-yl)-4,4,4-trifluoro-2-buten-1-one 在 Cinchona-alkaloid-thiourea 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以91%的产率得到4,4,4-trifluoro-3-(nitromethyl)-1-(1H-pyrazol-1-yl)butan-1-one
  参考文献：
  名称：

  Enantioselective Organocatalytic Michael Addition of Nitroalkanes and Other Nucleophiles to β-Trifluoromethylated Acrylamides

  摘要：

  An organocatalytic asymmetric Michael addition of nitroalkanes to trifluoromethylated acrylamides in good yields and with good to excellent diastereoselectivities and excellent enantioselectivities is described. The Michael adducts could be readily transformed into optically pure trifluoromethylated gamma-aminobutyric acid 7 in high yields without loss in enantioselectivities.

  DOI：

  10.1021/cs300806w
• 作为产物：
  描述：

  吡唑 、 4,4,4-三氟丁-2-烯酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 以52%的产率得到(E)-1-(pyrazol-1-yl)-4,4,4-trifluoro-2-buten-1-one
  参考文献：
  名称：

  Enantioselective Organocatalytic Michael Addition of Nitroalkanes and Other Nucleophiles to β-Trifluoromethylated Acrylamides

  摘要：

  An organocatalytic asymmetric Michael addition of nitroalkanes to trifluoromethylated acrylamides in good yields and with good to excellent diastereoselectivities and excellent enantioselectivities is described. The Michael adducts could be readily transformed into optically pure trifluoromethylated gamma-aminobutyric acid 7 in high yields without loss in enantioselectivities.

  DOI：

  10.1021/cs300806w

文献信息

• METHOD FOR ASYMMETRICALLY CATALYZED SYNTHESIS OF NITROPYRAZOLE AMIDE COMPOUND
  申请人：Zhejiang Jiuzhou Pharmaceutical Co., Ltd.

  公开号：EP3199525A1

  公开（公告）日：2017-08-02

  An asymmetrically catalyzed synthesis method of a γ-nitropyrazole amide compound is provided, wherein in the reaction that a nitroalkane and an α,β-unsaturated pyrazole amide are employed as raw materials, a complex formed by a chiral amine oxide with a rare earth metal compound is served as a catalyst, a 4 Å molecular sieve is served as an additive, after the reaction finished, to obtain a γ-nitropyrazole amide compound. The reaction has a yield more than 99% and an enantiomeric excess more than 99% ee. The catalytic system not only has the advantages of simple operation, mild reaction conditions, requiring no acid/base additives, convenient product purification, high yield and enatioselectivity, compliance with green atomic economy, and promising prospects for industrial application, but also allows the obtained γ-nitropyrazole amide compound to undergo some simple chemical conversions to produce some molecules having physiological activities.

  本发明提供了一种不对称催化合成γ-硝基吡唑酰胺化合物的方法，其中在以硝基烷烃和α,β-不饱和吡唑酰胺为原料的反应中，以手性氧化胺与稀土金属化合物形成的络合物为催化剂，以4埃分子筛为添加剂，反应结束后得到γ-硝基吡唑酰胺化合物。该反应的产率超过 99%，对映体过量率超过 99%ee。该催化体系不仅具有操作简单、反应条件温和、无需酸碱添加剂、产物纯化方便、收率和对映体选择性高、符合绿色原子经济、工业应用前景广阔等优点，而且可以使得到的γ-硝基吡唑酰胺化合物进行一些简单的化学转化，生成一些具有生理活性的分子。
• ASYMMETRICALLY CATALYZED SYNTHESIS METHOD OF NITROPYRAZOLE AMIDE COMPOUND
  申请人：Zhejiang Jiuzhou Pharmaceutical Co., Ltd.

  公开号：US20170291876A1

  公开（公告）日：2017-10-12

  A synthesis method of γ-nitropyrazole amide compound through asymmetrical catalyzing technique is provided, a nitroalkane and an α,β-unsaturated pyrazole amide are applied as the raw material, a complex formed by a chiral amine oxide with a rare earth metal compound is served as the catalyst, a 4 Å molecular sieve is served as an additive, the γ-nitropyrazole amide compound can be obtained with a yield more than 99% and enantiomeric excess more than 99% ee. The catalytic system not only has the advantages of simple operation, mild reaction conditions, requiring no acid/base additives, convenient product purification, high yield and enatioselectivity, compliance with green atomic economy, and promising prospects for industrial application, but also allows the obtained γ-nitropyrazole amide compound to undergo some simple chemical conversions to produce some molecules having physiological activities.