2-phenyl-1-(trifluoromethyl)-1H-benzo[b]thiophen-1-ium trifluoromethanesulfonate | 1214756-34-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-phenyl-1-(trifluoromethyl)-1H-benzo[b]thiophen-1-ium trifluoromethanesulfonate
• 英文别名: 2-phenyl-1-trifluoromethyl-benzo[b]thiophenium triflate；1-(trifluoromethyl)-2-phenylbenzo[b]thiophen-1-ium trifluoromethanesulfonate；S-(trifluoromethyl)-2-phenylbenzo[b]thiophenium trifluoromethanesulfonate；2-phenyl-1-(trifluoromethyl)-1-benzothiophen-1-ium;trifluoromethanesulfonate
• CAS: 1214756-34-9
• 化学式: CF₃O₃S*C₁₅H₁₀F₃S
• 分子量: 428.376
• InChiKey: OJUBKPZTKXBYID-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 、 2-phenyl-1-(trifluoromethyl)-1H-benzo[b]thiophen-1-ium trifluoromethanesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以59%的产率得到
  参考文献：
  名称：

  有效获取扩展的Yagupolskii–Umemoto型试剂：三氟乙酸催化邻乙炔基芳基三氟甲基硫烷的分子内环化

  摘要：

  环中之王：S-（三氟甲基）苯并[b]噻吩盐1作为Yagupolskii–Umemoto型试剂的类似物，是通过新颖的三氟甲磺酸催化的邻乙炔基芳基三氟甲基硫烷2的分子内环化反应合成的。1 j对于亲电性特别有用β-酮酸酯和二氰基亚烷基的三氟甲基化。

  DOI：

  10.1002/anie.200905225
• 作为产物：
  描述：

  三氟甲磺酸 、 1-(2-phenylethynyl)-2-trifluoromethylsulfanyl-benzene 以 二氯甲烷 为溶剂， 生成 2-phenyl-1-(trifluoromethyl)-1H-benzo[b]thiophen-1-ium trifluoromethanesulfonate
  参考文献：
  名称：

  有效获取扩展的Yagupolskii–Umemoto型试剂：三氟乙酸催化邻乙炔基芳基三氟甲基硫烷的分子内环化

  摘要：

  环中之王：S-（三氟甲基）苯并[b]噻吩盐1作为Yagupolskii–Umemoto型试剂的类似物，是通过新颖的三氟甲磺酸催化的邻乙炔基芳基三氟甲基硫烷2的分子内环化反应合成的。1 j对于亲电性特别有用β-酮酸酯和二氰基亚烷基的三氟甲基化。

  DOI：

  10.1002/anie.200905225

文献信息

• Silver-Mediated Trifluoromethylthiolation–Iodination of Arynes
  作者：Yuwen Zeng、Jinbo Hu

  DOI：10.1021/acs.orglett.6b00142

  日期：2016.2.19

  A one-pot trifluoromethylthiolation–iodination of arynes with trifluoromethylthiosilver (AgSCF3) and 1-iodophenylacetylene is described. This protocol allows rapid construction of o-trifluoromethylthiolated arene building blocks in moderate yields. These products were found to be excellent precursors for Yagupolskii–Umemoto-type electrophilic trifluoromethylation reagents.

  描述了用三氟甲基硫代银（AgSCF 3）和1-碘苯基乙炔对芳烃进行的一锅三氟甲基硫基化碘化反应。该方案允许以中等收率快速构建邻-三氟甲基硫醇化的芳烃结构单元。发现这些产品是Yagupolskii–Umemoto型亲电子三氟甲基化试剂的出色前体。
• TRIFLUOROMETHYLTHIOPHENIUM DERIVATIVE SALT, METHOD FOR PRODUCING THE SAME, AND METHOD FOR PRODUCING TRIFLUOROMETHYL-CONTAINING COMPOUNDS USING THE SAME
  申请人：Shibata Norio

  公开号：US20120130090A1

  公开（公告）日：2012-05-24

  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 R 1 , R 2 , R 3 , and R 4 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, R 5 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.

  本发明提供一种三氟甲基噻吩盐衍生物，可用作制药和农药的合成中间体，以及其制备方法和使用该盐衍生物制备含三氟甲基化合物的方法。S-(三氟甲基)-苯并[b]噻吩盐衍生物由下列普通式（1）表示：其中，R1、R2、R3和R4各自独立地是氢原子、甲基基团、乙基基团、具有3至10个碳原子的线性、支链或环烷基基团、甲氧基基团、乙氧基基团、具有3至10个碳原子的线性、支链或环烷氧基基团、氟原子、氯原子、溴原子、硝基或氰基，R5是甲基基团、乙基基团、具有3至10个碳原子的线性、支链或环烷基基团、苯基或取代苯基，X-表示阴离子。使用制备S-(三氟甲基)-苯并[b]噻吩盐衍生物的方法以及使用S-(三氟甲基)-苯并[b]噻吩盐衍生物作为三氟甲基化试剂可以制备各种三氟甲基含量的化合物。
• Trifluoromethylthiophenium derivative salt, method for producing the same, and method for producing trifluoromethyl-containing compounds using the same
  申请人：Shibata Norio

  公开号：US08703969B2

  公开（公告）日：2014-04-22

  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.

  提供了一种三氟甲基噻吩衍生物盐，可用作制药和农药的合成中间体，以及其制备方法和使用该盐制备三氟甲基含量化合物的方法。S-（三氟甲基）-苯并[b]噻吩盐的通用式（1）如下：其中R1、R2、R3和R4分别独立地是氢原子、甲基基团、乙基基团、具有3至10个碳原子的线性、支链或环状烷基基团、甲氧基基团、乙氧基基团、具有3至10个碳原子的线性、支链或环状烷氧基基团、氟原子、氯原子、溴原子、硝基或氰基，R5是甲基基团、乙基基团、具有3至10个碳原子的线性、支链或环状烷基基团、苯基或取代苯基，X-代表阴离子。使用制备S-（三氟甲基）-苯并[b]噻吩盐的方法和将S-（三氟甲基）-苯并[b]噻吩盐用作三氟甲基化试剂，可制备各种三氟甲基含量化合物。
• 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。
• TRIFLUOROMETHYLTHIOPHENIUM DERIVATIVE SALTS, PROCESS FOR PRODUCTION THEREOF, AND PROCESS FOR PRODUCTION OF TRIFLUOROMETHYL-CONTAINING COMPOUNDS USING SAME
  申请人：Nagoya Institute of Technology

  公开号：EP2460802B1

  公开（公告）日：2014-09-03