ethyl 1,3-diphenyl-5-trifluoromethyl-1H-pyrazole-4-carboxylate | 1092970-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1,3-diphenyl-5-trifluoromethyl-1H-pyrazole-4-carboxylate
• 英文别名: 3-phenyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester；Ethyl 1,3-diphenyl-5-(trifluoromethyl)pyrazole-4-carboxylate
• CAS: 1092970-81-4
• 化学式: C₁₉H₁₅F₃N₂O₂
• 分子量: 360.336
• InChiKey: SDYVHVNWZLQORC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 1,3-diphenyl-5-trifluoromethyl-Δ2-pyrazolin-4-carboxylate 在 2-碘酰基苯甲酸 作用下， 反应 0.17h， 生成 ethyl 1,3-diphenyl-5-trifluoromethyl-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  One-Pot Synthesis of Trifluoromethyl-Containing Pyrazoles via Sequential Yb(PFO)₃-Catalyzed Three-Component Reaction and IBX-Mediated Oxidation

  摘要：

  通过 Yb(PFO)3 催化芳香族肼、醛和三氟乙酰乙酸乙酯的三组分缩合，再通过 IBX 介导的吡唑啉氧化反应，合成了 14 种含三氟甲基的全取代吡唑。提出了一种可能的机理。

  DOI：

  10.1055/s-0028-1087348

文献信息

• The first chemoselective tandem acylation of the Blaise reaction intermediate: a novel method for the synthesis of α-acyl-β-enamino esters, key intermediate for pyrazoles
  作者：Yu Sung Chun、Ki Kon Lee、Young Ok Ko、Hyunik Shin、Sang-gi Lee

  DOI：10.1039/b813369g

  日期：——

  The Blaise reaction intermediate, a zinc bromide complex of β-enamino ester, could be activated in situ by addition of a stoichiometric or catalytic amount of n-BuLi to allow chemoselective tandem C2-acylation providing α-acyl-β-enamino esters, which are valuable intermediates for the syntheses of tri- and tetrasubstituted pyrazoles.

  布雷兹反应中间体是一种β-氨基酯的溴化锌复合物，可以通过添加计量或催化量的正丁基锂(n-BuLi)在原位激活，从而实现化学选择性的串联C2-酰基化，生成α-酰基-β-氨基酯，这些是合成三取代和四取代吡唑的重要中间体。
• Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides <i>via</i> a [[3 + 3] − 1] pathway
  作者：Bin Cheng、Bian Bao、Wei Xu、Yuntong Li、Hui Li、Xinping Zhang、Yun Li、Taimin Wang、Hongbin Zhai

  DOI：10.1039/d0ob00224k

  日期：——

  practical protocol for the synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides in excellent yields under mild conditions is described. The transformation proceeds via an unusual [[3 + 3] - 1] pathway, which involves a formal [3 + 3] cascade cyclization followed by a spontaneous ring-contraction/sulfur extrusion reaction from 4H-1,3,4-thiadiazine intermediates

  描述了一种新颖实用的方案，可在温和的条件下以极佳的收率由吡啶鎓1,4-两性离子硫醇盐和酰氯合成全取代的吡唑。转化是通过不寻常的[[3 + 3]-1]途径进行的，该途径涉及正式的[3 + 3]级联环化，然后由4H-1,3,4-噻二嗪中间体进行自发的环收缩/硫磺挤出反应。
• One-Pot Synthesis of Trifluoromethyl-Containing Pyrazoles via Sequential Yb(PFO)₃-Catalyzed Three-Component Reaction and IBX-Mediated Oxidation
  作者：Song Cao、Xuhong Qian、Li Shen、Jian Zhang、Jinlong Yu、Nianjin Liu、Jingjing Wu

  DOI：10.1055/s-0028-1087348

  日期：2008.12

  Fourteen trifluoromethyl-containing fully substituted pyrazoles were synthesized via Yb(PFO)3-catalyzed three-component condensations of aromatic hydrazines, aldehydes, and ethyl trifluoroacetoacetate, followed by IBX-mediated oxidation of pyrazolines. A possible mechanism is suggested.

  通过 Yb(PFO)3 催化芳香族肼、醛和三氟乙酰乙酸乙酯的三组分缩合，再通过 IBX 介导的吡唑啉氧化反应，合成了 14 种含三氟甲基的全取代吡唑。提出了一种可能的机理。