3-(trifluoromethyl)benzo[b]thiophene | 120568-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-(trifluoromethyl)benzo[b]thiophene
• 英文别名: 3-(trifluoromethyl)-1-benzothiophene
• CAS: 120568-05-0
• 化学式: C₉H₅F₃S
• 分子量: 202.2
• InChiKey: ABOQNJDBQHUXNW-UHFFFAOYSA-N

物化性质

• 沸点：
  232.3±35.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2,2,2-四氟苯乙酮 在 lithium hydroxide 、 diazabicycloundecane 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 水 、 乙腈 为溶剂， 反应 19.0h， 生成 3-(trifluoromethyl)benzo[b]thiophene
  参考文献：
  名称：

  Synthesis of substituted 3-trifluoromethylbenzo[b]thiophenes

  摘要：

  A straightforward method for the synthesis of 5/6-substituted 3-trifluoromethylbenzo[b]thiophenes and their precursor o-fluorinated trifluoro acetophenones is reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01811-2

文献信息

• Cathodic C–H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex
  作者：Wolfgang Jud、Snjezana Maljuric、C. Oliver Kappe、David Cantillo

  DOI：10.1021/acs.orglett.9b02948

  日期：2019.10.4

  While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex

  尽管已经报道了一些涉及通过阳极氧化电化学生成CF3自由基的三氟甲基化反应，但替代性的阴极，还原自由基的生成仍然难以捉摸。在此，报道了芳烃和杂芳烃的第一次阴极三氟甲基化。该方法基于电化学还原由廉价的三氟氯甲烷和三乙胺就地生成的不稳定的三氟三乙铵络合物，该络合物产生 自由基，这些自由基被芳烃捕获在阴极表面上。
• Trifluoromethylation of aromatic compounds with bis(trifluoroacetyl) peroxide
  作者：Hideo Sawada、Masaharu Nakayama、Masato Yoshida、Tatsuro Yoshida、Nobumasa Kamigata

  DOI：10.1016/s0022-1139(00)82927-9

  日期：1990.3

  Bis(trifluoroacety) peroxide was found to be thermally stable, and trifluoromenthylation of aromatic compounds was studied using this peroxide. Thrifluoromethylation of electron-rich benzenes, furan, thiophene, or their benzo derivatives proceeded with the peroxide in moderate to high yields.

  发现双（三氟乙氧基）过氧化物是热稳定的，并且使用该过氧化物研究了芳族化合物的三氟乙酰化。富电子的苯，呋喃，噻吩或其苯并衍生物的三氟甲基化与过氧化物一起以中等至高收率进行。
• Photochemical Trifluoromethylation of Some Aromatic and Heteroaromatic Compounds with Trifluoromethyl Bromide
  作者：Takeo Akiyama、Kohji Kato、Masatsugu Kajitani、Yoshio Sakaguchi、Junko Nakamura、Hisaharu Hayashi、Akira Sugimori

  DOI：10.1246/bcsj.61.3531

  日期：1988.10

  The photochemical introduction of trifluoromethyl group with CF3Br in aromatic and heteroaromatic rings was investigated for 9 compounds. Naphthalene, anthracene, anisole, N,N-dimethylaniline, ferrocene, benzo[b]thiophene, isoquinoline, and N-methylpyrrole gave trifluoromethylated products in 6.5–100% yields. In one step from uracil, a pharmacologically important 5-trifluoromethyluracil can be synthesized

  研究了 9 种化合物在芳环和杂芳环中三氟甲基与 CF3Br 的光化学引入。萘、蒽、苯甲醚、N,N-二甲基苯胺、二茂铁、苯并[b]噻吩、异喹啉和 N-甲基吡咯以 6.5-100% 的产率得到三氟甲基化产物。在尿嘧啶的一个步骤中，一种药理学上重要的 5-三氟甲基尿嘧啶可以通过这种方法以 11% 的产率合成。根据对萘-CF3Br-CH3CN 系统进行的机理研究，发现反应是通过电子从萘的激发单线态转移到 CF3Br 进行的。
• An improved synthesis of substituted benzo[b]thiophenes using microwave irradiation
  作者：Daniel Allen、Owen Callaghan、Frederic L. Cordier、David R. Dobson、John R. Harris、Terry M. Hotten、W. Martin Owton、Richard E. Rathmell、Virginia A. Wood

  DOI：10.1016/j.tetlet.2004.11.005

  日期：2004.12

  An easy and high-yielding method for the synthesis of substituted benzo[b]thiophenes using microwave irradiation is described.

  描述了一种利用微波辐射合成取代的苯并[ b ]噻吩的简便且高产的方法。
• TRIFLUOROMETHYLTHIOPHENIUM DERIVATIVE SALTS, PROCESS FOR PRODUCITON THEREOF, AND PROCESS FOR PRODUCTION OF TRIFLUOROMETHYL-CONTAINING COMPOUNDS USING SAME
  申请人：Nagoya Institute of Technology

  公开号：EP2460802A1

  公开（公告）日：2012-06-06

  A trifluoromethylthiophenium derivative salt useful as synthetic intermediates for pharmaceuticals and agrochemicals, a method for producing the same, and a method for producing trifluoromethyl-containing compounds using the same are provided. An S-(trifluoromethyl)-benzo[b]thiophenium derivative salt is represented by the following general formula (1): wherein R1, R2, R3, and R4 are each independently a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkyloxy group having 3 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, or a cyano group, R5 is a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, or a substituted phenyl group, and X- represents an anion. Various trifluoromethyl-containing compounds are produced using a method for producing the S-(trifluoromethyl)-benzo[b]thiophenium derivative salt, and using the S-(trifluoromethyl)-benzo[b]thiophenium derivative salt as a trifluoromethylating agent.

  本发明提供了一种可用作医药和农用化学品合成中间体的三氟甲基噻吩衍生物盐、生产该衍生物盐的方法以及使用该衍生物盐生产含三氟甲基化合物的方法。一种 S-(三氟甲基)-苯并[b]噻吩衍生物盐由以下通式(1)表示： 其中 R1、R2、R3 和 R4 各自独立地为氢原子、甲基、乙基、具有 3 至 10 个碳原子的直链、支链或环状烷基、甲氧基、乙氧基、具有 3 至 10 个碳原子的直链、支链或环状烷氧基、氟原子、氯原子、溴原子、硝基或氰基，R5 是甲基、乙基、具有 3 至 10 个碳原子的直链、支链或环状烷基、苯基或取代苯基，X- 代表阴离子。使用生产 S-(三氟甲基)-苯并[b]噻吩衍生物盐的方法，并使用 S-(三氟甲基)-苯并[b]噻吩衍生物盐作为三氟甲基化剂，可生产出各种含三氟甲基的化合物。