3,4-bis(trifluoromethyl)-pyrazole | 19968-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-bis(trifluoromethyl)-pyrazole
• 英文别名: 3,4-bis(trifluoromethyl)pyrazole；3,4-bis-trifluoromethyl-1(2)H-pyrazole；3,4-Bis-(trifluormethyl)-pyrazol；3,4-Bis(trifluoromethyl)-1H-pyrazole；4,5-bis(trifluoromethyl)-1H-pyrazole
• CAS: 19968-19-5
• 化学式: C₅H₂F₆N₂
• 分子量: 204.075
• InChiKey: OERNNUCUUZXPBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙氧基-2-亚甲基三氟乙酰乙酸乙酯 在 盐酸 、 sulfur tetrafluoride 、 氢氟酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 30.0h， 生成 3,4-bis(trifluoromethyl)-pyrazole
  参考文献：
  名称：

  “Reported, but Still Unknown.” A Closer Look into 3,4-Bis- and 3,4,5-Tris(trifluoromethyl)pyrazoles

  摘要：

  Straightforward practical synthetic approaches to 3,4-bis- and 3,4,5-tris(trifluoromethyl)pyrazoles have been developed. The key step of the both syntheses is a transformation of the carboxylic group in a pyrazole core into the trifluoromethyl group by sulfur tetrafluoride. The elaborated synthetic protocols allow gram-scale preparation of the target products. The obtained compounds are comprehensively characterized by means of crystallographic analysis, determination of pK(a) values and fluorescence measurements.

  DOI：

  10.1021/jo202305c

文献信息

• [3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles
  作者：Yuriy N. Маrkitanov、Vadim М. Тimoshenko、Sergiy S. Мykhaylychenko、Eduard B. Rusanov、Alexandr I. Khyzhan、Yuriy G. Shermolovich

  DOI：10.1007/s10593-021-03029-8

  日期：2021.11

  1,3-Dipolar cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing a sulfonyl, sulfamide, or sulfoximine substituent in position 1 with diazomethane proceed with the formation of 3-substituted 4-(trifluoromethyl)-4,5-dihydro-1H-pyrazoles and 3-(trifluoromethyl)-1H-pyrazole, whereas reactions with ethyl diazoacetate and 2,2,2-trifluorodiazoethane lead to the formation of isomeric 5(3)-substituted

  在 1 位含有磺酰基、磺酰胺或亚砜亚胺取代基的 3,3,3-三氟丙烯衍生物与重氮甲烷发生 1,3-偶极环加成反应，形成 3-取代的 4-（三氟甲基）-4,5-二氢- 1 H-吡唑和 3-(三氟甲基)-1 H-吡唑，而与重氮乙酸乙酯和 2,2,2-三氟重氮乙烷的反应导致形成异构的 5(3)-取代的 4-三氟甲基-3,4(4 ,5)-二氢-2(1) H-吡唑和 4-取代的 5-(三氟甲基)-4,5-二氢-1 H吡唑，其稳定性取决于杂原子取代基的性质。3,3,3-三氟丙烯的 1-磺酰基-和 1-氨磺酰基取代衍生物与C的环加成反应-carbethoxy- N-苯基腈亚胺产生4-取代的1-苯基-5-(三氟甲基)-4,5-二氢-1H-吡唑-3-羧酸乙酯和1-苯基-4-(三氟甲基)-1乙酯H-吡唑-3-羧酸盐。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.1, 5.2.1.2, page 75 - 81
  作者：

  DOI：——

  日期：——
• 1,3-Dipolar cycloaddition reactions of a diphosphabarrelene
  作者：Yoshiro Kobayashi、Itsumaro Kumadaki、Akio Ohsawa、Hiroshi Hamana

  DOI：10.1016/s0040-4039(01)92777-7

  日期：1977.1
• Studies on organic fluorine compounds. 29. Cycloaddition reactions of hexakis(trifluoromethyl)-1,4-diphosphabarrelene
  作者：Yoshiro Kobayashi、Hiroshi Hamana、Shomi Fujino、Akio Ohsawa、Itsumaro Kumadaki

  DOI：10.1021/jo00394a038

  日期：1979.12
• “Reported, but Still Unknown.” A Closer Look into 3,4-Bis- and 3,4,5-Tris(trifluoromethyl)pyrazoles
  作者：Igor I. Gerus、Roman X. Mironetz、Ivan S. Kondratov、Andrei V. Bezdudny、Yurii V. Dmytriv、Oleg V. Shishkin、Viktoriia S. Starova、Olga A. Zaporozhets、Andrey A. Tolmachev、Pavel K. Mykhailiuk

  DOI：10.1021/jo202305c

  日期：2012.1.6

  Straightforward practical synthetic approaches to 3,4-bis- and 3,4,5-tris(trifluoromethyl)pyrazoles have been developed. The key step of the both syntheses is a transformation of the carboxylic group in a pyrazole core into the trifluoromethyl group by sulfur tetrafluoride. The elaborated synthetic protocols allow gram-scale preparation of the target products. The obtained compounds are comprehensively characterized by means of crystallographic analysis, determination of pK(a) values and fluorescence measurements.