5-(2-噻吩基)-3-(三氟甲基)-1H-吡唑 | 26974-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(2-噻吩基)-3-(三氟甲基)-1H-吡唑
• 英文名称: 5-(thiophen-2-yl)-3-(trifluoromethyl)-1H-pyrazole
• 英文别名: 3-thiophen-2-yl-5-(trifluoromethyl)-1H-pyrazole
• CAS: 26974-16-3
• 化学式: C₈H₅F₃N₂S
• mdl: MFCD00459838
• 分子量: 218.202
• InChiKey: RAQSZNBGFKBCNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(2-噻吩基)-3-(三氟甲基)-1H-吡唑 在 氨 、 水 作用下， 反应 24.0h， 以80%的产率得到5-(thien-2-yl)-1H-pyrazole-3-carbonitrile
  参考文献：
  名称：

  Synthesis of 3-Cyanopyrazoles from 3-Trifluoromethyl-pyrazoles via Direct Ammonolysis Reaction

  摘要：

  A simple and green method to prepare 3-cyanopyrazoles in aqueous ammonia from easy-obtained 3-trifluoromethyl-pyrazoles was explored. Most substrates got acceptable yields. The hydrogen position of Nl-H on cyanopyrazoles was assigned by X-ray crystal structure analysis.

  DOI：

  10.3987/com-11-12399
• 作为产物：
  描述：

  2-乙酰基噻吩 在 sodium methylate 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 38.0h， 生成 5-(2-噻吩基)-3-(三氟甲基)-1H-吡唑
  参考文献：
  名称：

  Novel potent and selective calcium-release-activated calcium (CRAC) channel inhibitors. Part 2: Synthesis and inhibitory activity of aryl-3-trifluoromethylpyrazoles

  摘要：

  To identify potent and selective calcium-release-activated calcium (CRAG) channel inhibitors, we examined the structure-activity relationships of the pyrazole and thiophene moieties in compound 4. Compound 25b was found to exhibit highly potent and selective inhibitory activity for CRAC channels and further modifications of the pyrazole and benzoyl moieties of compound 25b produced compound 29. These compounds were potent inhibitors of IL-2 production in vitro and also acted as inhibitors in pharmacological models of diseases resulting from T-lymphocyte activation, after oral administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.039

文献信息

• Silver-Mediated Cycloaddition of Alkynes with CF₃CHN₂: Highly Regioselective Synthesis of 3-Trifluoromethylpyrazoles
  作者：Feng Li、Jing Nie、Long Sun、Yan Zheng、Jun-An Ma

  DOI：10.1002/anie.201301870

  日期：2013.6.10

  Silver screen: The title reaction provides a convenient and efficient method for the construction of 5‐substituted 3‐trifluoromethylpyrazoles under mild reaction conditions. By using this protocol, the marketed drug Celecoxib (antiarthritic) could be easily synthesized (see scheme; DMF=N,N‐dimethylformamide).

  银屏：标题反应为在温和的反应条件下构建5取代的3-三氟甲基吡唑提供了一种方便而有效的方法。通过使用该协议，可以轻松合成市售药物塞来昔布（抗关节炎药）（参见方案； DMF = N，N-二甲基甲酰胺）。
• Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene
  作者：Chuanle Zhu、Hao Zeng、Chi Liu、Yingying Cai、Xiaojie Fang、Huanfeng Jiang

  DOI：10.1021/acs.orglett.9b04228

  日期：2020.2.7

  is reported that occurs by the three-component coupling of environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP), aldehydes, and sulfonyl hydrazides. This highly regioselective three-component reaction is metal-free, catalyst-free, and operationally simple and features mild conditions, a broad substrate scope, high yields, and valuable functional group

  据报道，通过环境友好的大吨位工业原料2-溴-3,3,3-三氟丙烯（BTP），醛和磺酰肼的三组分偶联，可以实现3-三氟甲基吡唑合成的通用和实用策略。这种高度区域选择性的三组分反应不含金属，不含催化剂，操作简单，具有条件温和，底物范围广，收率高和有价值的官能团耐受性。值得注意的是，反应可以在100 mmol的规模上进行，并顺利提供了塞来昔布，马伐昔布，SC-560和AS-136A合成的关键中间体。初步机理研究表明，此转化过程涉及1,3-氢原子转移过程。
• Cycloaddition of Trifluoroacetaldehyde <i>N</i>-Triftosylhydrazone (TFHZ-Tfs) with Alkynes for Synthesizing 3-Trifluoromethylpyrazoles
  作者：Hongwei Wang、Yongquan Ning、Yue Sun、Paramasivam Sivaguru、Xihe Bi

  DOI：10.1021/acs.orglett.0c00395

  日期：2020.3.6

  (TFHZ-Tfs) and alkynes is reported. This protocol provides an operationally simple and general method for the synthesis of diverse 3-trifluoromethylpyrazoles in good to excellent yields with broad substrate scope, including aryl, heteroaryl, and alkyl terminal alkynes, and electron-deficient internal alkynes. The synthetic potential of this method was further demonstrated by the synthesis of an antiarthritic

  据报道，三氟乙醛N-三氟yl（TFHZ-Tfs）与炔烃之间无过渡金属的[3 + 2]环加成反应。该协议提供了一种操作简单且通用的方法，可以以良好的产率和优异的产率合成各种3-三氟甲基吡唑，具有广泛的底物范围，包括芳基，杂芳基和烷基末端炔烃，以及电子缺陷型内部炔烃。通过抗克药物塞来昔布的合成（以克为单位），进一步证明了该方法的合成潜力。
• Trivalent Rare Earth Complexes of the Unsymmetrical 3‐(2′‐Thienyl)‐5‐(trifluoromethyl)pyrazolate Ligand
  作者：Glen B. Deacon、Peter C. Junk、Aron Urbatsch

  DOI：10.1002/ejic.201100487

  日期：2011.8

  Trivalent rare earth complexes of the unsymmetrical 3-(2'-thienyl)-5-(trifluoromethyl)pyrazolate (ttfpz) ligand, namely [RE(ttfpz)(3)(thf)(3)]center dot nsolv, where thf = tetrahydrofuran [RE = La, solv = PhMe, n = 0.5 (1); RE = Sm, n = 0 (2); RE = Tb, solv = thf, n = 1 (3)], [RE(ttfpz)(3)(thf)(2)] [RE = Y (4), Ho (5), Lu (6), Sc (7)] and [RE(ttfpz)(3)(dme)(2)]center dot nsolv, where dme = 1,2-dimethoxyethane

  不对称 3-(2'-噻吩基)-5-(三氟甲基)吡唑 (ttfpz) 配体的三价稀土配合物，即 [RE(ttfpz)(3)(thf)(3)] 中心点 nsolv，其中 thf =四氢呋喃 [RE = La, solv = PhMe, n = 0.5 (1); RE = Sm, n = 0 (2); RE = Tb, solv = thf, n = 1 (3)], [RE(ttfpz)(3)(thf)(2)] [RE = Y (4), Ho (5), Lu (6), Sc (7)] 和 [RE(ttfpz)(3)(dme)(2)] 中心点 nsolv，其中 dme = 1,2-二甲氧基乙烷 [RE = La, n = 0 (8a); RE = La，solv = Et2O，n = 0.5 (8b)；RE = Eu，solv = dme，n = 1 (9)]，主要通过游离金属 Hg(C6F5)(2)
• Pharmaceutical compound comprising a pyrazole derivative and methods of using the same for the treatment of calcium release-activated calcium channel associated diseases
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06348480B1

  公开（公告）日：2002-02-19

  The present invention is directed to drugs, in particular, pyrazole derivatives represented by the following general formula (I) which have a calcium release-activated calcium channel inhibitory effect and medicinal compositions, in particular, calcium release-activated calcium channel inhibitors containing the above compounds as the active ingredient, wherein each substituent is defined in the specification. The present invention also relates to a pharmaceutical composition containiing an effective amount of the compound of formula (I) and a pharmaceutically effective carrier. The present invention further relates to methods of treatment of diseases associated with calcium release-activated calcium channels, diseases associated with IL-2 production, and methods of treatment of allergic, inflammatory or auto-immune diseases.

  本发明涉及药物，特别是由以下一般式（I）表示的吡唑衍生物，其具有钙释放激活的钙通道抑制作用和药用组合物，特别是含有上述化合物作为活性成分的钙释放激活的钙通道抑制剂，其中每个取代基在规范中定义。本发明还涉及含有一定量的式（I）化合物和药效载体的药用组合物。本发明还涉及与钙释放激活的钙通道相关的疾病、与IL-2产生相关的疾病以及过敏、炎症或自身免疫疾病的治疗方法。