1-methyl-2-((trifluoromethyl)sulfinyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-methyl-2-((trifluoromethyl)sulfinyl)-1H-pyrrole
• 英文别名: 2-[(trifluoromethyl)sulfinyl]-N-methyl-1H-pyrrole；1-methyl-2-(trifluoromethanesulfinyl)-1H-pyrrole；1-methyl-2-trifluoromethylsulfinylpyrrole；Trifluoromethyl(1-methyl-1H-pyrrole-2-yl) sulfoxide；1-methyl-2-(trifluoromethylsulfinyl)pyrrole
• 化学式: C₆H₆F₃NOS
• 分子量: 197.181
• InChiKey: QZWRKIYVFCDIOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基吡咯 、 Langlois reagent 在 三氯氧磷 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以60%的产率得到1-methyl-2-((trifluoromethyl)sulfinyl)-1H-pyrrole
  参考文献：
  名称：

  CF 3 S（O）+阳离子的新等价物。三氟甲烷亚磺酸盐和三氟甲烷亚磺酰胺的合成

  摘要：

  三氟甲烷亚磺酸钠（“三氟甲磺酸钠”）和磷酰氯（）在AcOEt中的溶液的行为相当于CF 3 S（O）+阳离子的当量。它可以在室温下原位分别由醇或胺制备三氟甲亚磺酸盐（CF 3 S（O）OR）或三氟甲亚磺酰胺（CF 3 S（O）NHR）。

  DOI：

  10.1016/s0040-4020(99)00364-6

文献信息

• Transition‐Metal‐Free Electrophilic Fluoroalkanesulfinylation of Electron‐Rich (Het)Arenes with Fluoroalkyl Heteroaryl Sulfones via C(Het)−S and S=O Bond Cleavage
  作者：Jun Wei、Kun Bao、Chengcheng Qi、Yao Liu、Chuanfa Ni、Rong Sheng、Jinbo Hu

  DOI：10.1002/adsc.201900959

  日期：2019.12.17

  A novel Ph2P(O)Cl‐mediated direct fluoroalkanesulfinylation of electron‐rich (het)arenes using fluoroalkyl heteroaryl sulfones as the RfSO source (Rf=C4F9, CF2Cl, CF2Br, and CF2COOEt) was developed. This is the first example where 2‐HetSO2Rf performs as the RfSO synthon in organic synthesis via both C(Het)−S and S=O bond cleavage.

  使用氟代烷基杂芳基砜作为R f SO源（R f = C 4 F 9，CF 2 Cl，CF 2 Br和CF ）的新型Ph 2 P（O）Cl介导的富电子（杂）芳烃的直接氟代烷烃亚磺酰化2 COOEt）的开发。这是第一个例子，其中2-HetSO 2 R f通过C（Het）-S和S = O键断裂在有机合成中充当R f SO合成子。
• Environment friendly reagents and process for halogenoalkylsulfinylation of organic compounds
  申请人：VIRBAC S.A.

  公开号：EP1331222A1

  公开（公告）日：2003-07-30

  The invention concerns compounds corresponding to formula (I) : wherein: Y represents a group chosen from : a C1-C20, linear, branched or cyclic alkane di-yl, or alkene di-yl, or alkyne di-yl radical, wherein said alkane, alkene or alkyne chain can be substituted by one or more groups chosen from : a phenyl ring or a halogen atom, and said alkane, alkene or alkyne chain can comprise a sulfur bridge or an oxygen bridge ; R represents an alkyl group, linear or branched, comprising one to four carbon atoms and substituted by one or more, identical or different, halogen atoms ; a process for their preparation and their use as halogenoalkylsulfinylating agents.

  该发明涉及与以下公式（I）对应的化合物：其中：Y代表从中选择的一组基团：C1-C20的直链、支链或环烷烃二基、烯烃二基或炔烃二基，其中所述的烷烃、烯烃或炔烃链可以被一个或多个从以下选择的基团取代：苯环或卤素原子，并且所述的烷烃、烯烃或炔烃链可以包含硫桥或氧桥；R代表一个含有一到四个碳原子的直链或支链烷基，并且被一个或多个相同或不同的卤素原子取代；一种用于它们的制备和作为卤代烷基磺酰化剂的使用方法。
• Interrupted reduction of CF 3 SO 2 Cl using tricyclohexylphosphine allows for electrophilic trifluoromethylsulfinylation
  作者：Hélène Chachignon、Dominique Cahard

  DOI：10.1016/j.jfluchem.2016.11.020

  日期：2017.6

  The monoreduction of trifluoromethanesulfonyl chloride by an appropriate phosphine, preferentially tricyclohexylphosphine, generates the reactive trifluoromethanesulfinyl chloride CF3SOCl as donor of CF3S(O)+ cation. The direct trifluoromethylsulfinylation of indoles, pyrroles, other azaarenes, amines, and phenols was successfully achieved in moderate to high yields.

  通过适当的膦（最好是三环己基膦）对三氟甲磺酰氯进行单还原可生成反应性三氟甲磺酰氯CF 3 SOCl，作为CF 3 S（O）+阳离子的供体。吲哚，吡咯，其他氮杂芳烃，胺和苯酚的直接三氟甲基亚磺酰化已成功实现中度至高产率。
• Synthesis and reactivity of a stable crystalline diastereomerically pure trifluoromethanesulfinic acid derivative: (S)-(−)-1-trifluoromethylsulfinyl-(R)-4-phenyloxazolidin-2-one
  作者：Vadim D. Romanenko、Claire Thoumazet、Vincent Lavallo、Fook S. Tham、Guy Bertrand

  DOI：10.1039/b303574c

  日期：——

  Efficient synthesis of the title compound, the first diastereomerically pure trifluoromethanesulfinic acid derivative (8), has been achieved by direct trifluoromethanesulfinylation of the lithiated (4R)-(−)-4-phenyloxazolidin-2-one; in contrast to the reaction between CF3S(O)Cl and (1R,2S,5R)-(−)-menthol which occurs with low stereoselectivity ( 98% de.

  通过锂化 (4R)-(-)-4-phenyloxazolidin-2-one 的直接三氟甲烷亚磺酰化，实现了标题化合物的高效合成，这是第一个非对映异构纯的三氟甲亚磺酸衍生物 (8)；与 CF3S(O)Cl 和 (1R,2S,5R)-(-)-薄荷醇之间的反应相反，该反应以低立体选择性 (98% de.
• [EN] ENVIRONMENT FRIENDLY REAGENTS AND PROCESS FOR TRIFLUOROMETHYLSULFINYLATION OF ORGANIC COMPOUNDS<br/>[FR] REACTIFS SANS DANGER POUR L'ENVIRONNEMENT ET PROCEDE DE TRIFLUOROMETHYLSULFINYLATION DE COMPOSES ORGANIQUES
  申请人：VIRBAC SA

  公开号：WO2003064384A2

  公开（公告）日：2003-08-07

  The invention relates to new trifluoromethylsulfinylimide reagents, corresponding to formula (I): wherein Y represents a group chosen from : a C1-C20, linear, branched or cyclic alkane di-yl, or alkene di-yl, or alkyne di-yl radical, wherein said alkane, alkene or alkyne chain can be substituted by one or more groups chosen from : a phenyl ring or a halogen atom, like for example F, Cl, Br, I, wherein said alkane, alkene or alkyne chain can comprise a sulfur bridge or an oxygen bridge ; a process for their preparation and their use as trifluoromethylsulfinylating agents.