(E)-1-(3,5-dimethyl-1H-pyrazol-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(3,5-dimethyl-1H-pyrazol-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one
• 英文别名: 1-[3-(4-chlorophenyl)acryloyl]-3,5-dimethyl-1H-pyrazole；(E)-3-(4-chlorophenyl)-1-(3,5-dimethylpyrazol-1-yl)prop-2-en-1-one
• 化学式: C₁₄H₁₃ClN₂O
• 分子量: 260.723
• InChiKey: WQPIPWXDZCGVSB-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,5-dimethyl-1H-pyrazol-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one 、 2,3-二甲基-1,3-丁二烯 在 C₃₈H₃₈N₄RhS₂⁽¹⁺⁾*F₆P^(1-) 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  分子间[2+2]光环加成的直接可见光激发不对称路易斯酸催化

  摘要：

  报道了一种反应设计，其中底物结合的手性路易斯酸配合物吸收可见光并产生激发态，该激发态以高度立体控制的方式直接与共底物反应。具体来说，手性铑配合物催化可见光激活的分子间 [2+2] 环加成，提供各种环丁烷，其 ee 高达 >99%，dr 高达 >20:1 值得注意的是能够产生邻位全-碳四元立体中心，包括分子间形式的螺中心。

  DOI：

  10.1021/jacs.7b04363
• 作为产物：
  描述：

  3,5-二甲基吡唑 、 对氯肉桂酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以45 %的产率得到(E)-1-(3,5-dimethyl-1H-pyrazol-1-yl)-3-(4-chlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  磺酰氯对 α,β-不饱和羰基的光催化对映选择性氢磺酰化

  摘要：

  利用易于获得的磺酰氯，并通过可见光照射与手性镍催化相结合，建立了 α,β-不饱和羰基的有效对映选择性氢磺酰化。该方案能够生产各种具有显着对映选择性的 α-手性砜。

  DOI：

  10.1002/anie.202312780

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：US10464899B2

  公开（公告）日：2019-11-05

  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.

  提供了一种通过不对称催化技术合成γ-硝基吡唑酰胺化合物的方法，以硝基烷烃和α,β-不饱和吡唑酰胺为原料，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，可获得收率大于99%、对映体过量率大于99%ee的γ-硝基吡唑酰胺化合物。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.