2-(trifluoromethyl)phenyl 4-methylbenzenesulfonate | 1389834-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(trifluoromethyl)phenyl 4-methylbenzenesulfonate
• 英文别名: [2-(Trifluoromethyl)phenyl] 4-methylbenzenesulfonate
• CAS: 1389834-56-3
• 化学式: C₁₄H₁₁F₃O₃S
• 分子量: 316.301
• InChiKey: FDCBXEBDCWUXBN-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C
• 沸点：
  395.9±42.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(trifluoromethyl)phenyl 4-methylbenzenesulfonate 、 苯硼酸 在 1,1'-双(二苯基膦)二茂铁 、 (9-phenanthrenyl)Ni(II)(PPh₃)2Cl 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以70%的产率得到1-苯基-2-(三氟甲基)苯
  参考文献：
  名称：

  用于芳基甲苯磺酸盐与芳基硼酸的有效交叉偶联反应的镍预催化剂：dppf的重要作用

  摘要：

  检查了空气稳定且易于处理的镍预催化剂（9-菲基）Ni（II）（PPh 3）2 Cl的芳基甲苯磺酸盐与芳基硼酸的交叉偶联反应。在优化的反应条件下，催化系统可耐受各种活化，中性和失活的底物。已经研究了该交叉偶联反应对芳基甲苯磺酸酯和芳基硼酸的选择性。建议配体1,1'-双（二苯基膦基）二茂铁（dppf）通过在关键中间体和活性Ni（0）物种中强制实施顺式几何构型，在偶联中起关键作用。

  DOI：

  10.1016/j.tet.2014.04.059
• 作为产物：
  描述：

  邻三氟甲基苯酚 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以97%的产率得到2-(trifluoromethyl)phenyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates

  摘要：

  Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding the simplicity, reaction time and conditions, the range of substrates, yields, and environmental friendliness.

  DOI：

  10.1055/s-0034-1378867

文献信息

• PROCESS FOR PRODUCING AROMATIC AMINES
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20020035295A1

  公开（公告）日：2002-03-21

  The present invention provides an activator in arylamination using a palladium compound as a catalyst, which is superior to conventional phosphines in stability and performance. With the phosphine sulfide as an activator, an arylamination reaction achieves improved selectivity to produce a desired aromatic amine in an obviously increased yield as compared with a reaction using the corresponding phosphine compound. Moreover, the phosphine sulfide of the invention is impervious to oxidation and exists stably in air and therefore sufficiently withstands use on an industrial scale.

  本发明提供了一种在芳基化反应中使用钯化合物作为催化剂的活化剂，其在稳定性和性能方面优于传统的膦化合物。通过使用膦硫化物作为活化剂，芳基化反应实现了改善的选择性，以明显增加的产量生产所需的芳香胺，与使用相应的膦化合物的反应相比。此外，本发明的膦硫化物不受氧化影响，在空气中存在稳定，因此足以在工业规模上使用。
• Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel
  作者：Xiaolei Huang、Shenghan Teng、Yonggui Robin Chi、Wenqiang Xu、Maoping Pu、Yun‐Dong Wu、Jianrong Steve Zhou

  DOI：10.1002/anie.202011036

  日期：2021.2.8

  Nickel‐catalyzed intermolecular Heck reaction of cycloalkenes proceeds well with aryl triflates, mesylates and tosylates in excellent enantiomeric ratios. The asymmetric reductive Heck reaction also works with a 2‐cyclopentenone ketal, which is equivalent to conjugate arylation of the enone itself.

  镍催化的环烯烃的分子间Heck反应与芳基三氟甲磺酸酯，甲磺酸酯和甲苯磺酸酯的对映体比率极好。不对称的还原性Heck反应也适用于2-环戊烯酮缩酮，这相当于烯酮本身的共轭芳基化。
• Nickel‐Catalyzed C( <i>sp</i> ² )−C( <i>sp</i> ³ ) Kumada Cross‐Coupling of Aryl Tosylates with Alkyl Grignard Reagents
  作者：Aleksandra Piontek、Wioletta Ochędzan‐Siodłak、Elwira Bisz、Michal Szostak

  DOI：10.1002/adsc.201801586

  日期：2019.5.14

  Aryl tosylates are an attractive class of electrophiles for cross‐coupling reactions due to ease of synthesis, low price, and the employment of C−O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni‐catalyzed C(sp2)−C(sp3) Kumada cross‐coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross‐coupling

  由于易于合成，价格低廉和使用C-O亲电试剂，芳基甲苯磺酸盐是用于交叉偶联反应的一类亲电试剂，但是，芳基甲苯磺酸盐的反应性很低。在此，我们报告了Ni催化的C（sp 2）-C（sp 3）Kumada将芳基甲苯磺酸盐与伯烷基和仲烷基格氏试剂进行交叉偶联。该方法通过与具有β-氢的具有挑战性的烷基有机金属交叉偶联，从而提供有价值的烷基芳烃，这些金属容易发生β-氢化物消除和均相偶联。该反应由空气和湿气稳定的Ni（II）预催化剂催化。各种各样的电子可变的芳基甲苯磺酸盐，包括双甲苯磺酸盐，都经历了这种转变，许多例子都适合在温和的室温条件下使用。Ar-X交叉偶联与简便的Ar-OH活化/交叉偶联策略相结合，可以与具有挑战性的烷基有机金属进行正交交叉偶联。此外，我们证明了该方法可在TON达到2000的情况下运行，
• 2,2 (Diarlyl) Vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst
  申请人：——

  公开号：US20020058837A1

  公开（公告）日：2002-05-16

  A novel 2,2-(diaryl)vinylphosphine compound represented by the following general formula (1): 1 (wherein R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc.; R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 may be the same or different and each is an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc., provided that R 4 and R 5 taken together and/or R 6 and R 7 taken together may represent a fused benzene ring, a substituted fused benzene ring, a trimethylene group, etc.; and p, q, r, and s each is 0 to 5, provided that p+q and r+s each is in the range of from 0 to 5); a palladium-phosphine catalyst obtained by causing a palladium compound to act on the novel 2,2-(diaryl)vinylphosphine compound; and a process for obtaining an arylamine, a diaryl and an arylalkyne in the presence of the palladium-phosphine catalyst.

  一种由以下通用公式（1）表示的新型2,2-(二芳基)乙烯膦化合物：其中R1是氢原子、具有1至6个碳原子的烷基基团、具有5至7个碳原子的脂环基团等；R2、R3、R4、R5、R6和R7可能相同或不同，每个是具有1至6个碳原子的烷基基团、具有5至7个碳原子的脂环基团等，但要求R4和R5一起和/或R6和R7一起可能代表融合苯环、取代融合苯环、三亚甲基基团等；p、q、r和s每个为0至5，但要求p+q和r+s分别在0至5的范围内；通过使钯化合物作用于新型2,2-(二芳基)乙烯膦化合物而获得的钯-膦催化剂；以及在钯-膦催化剂存在下获得芳胺、二芳基和芳基炔的方法。
• NONAQUEOUS ELECTROLYTE SOLUTION, ELECTRICITY STORAGE DEVICE USING SAME, AND TRIFLUOROMETHYLBENZENE COMPOUND
  申请人：ABE Koji

  公开号：US20140038060A1

  公开（公告）日：2014-02-06

  The present invention is to provide a nonaqueous electrolytic solution capable of enhancing electrochemical characteristics in a broad temperature range, an energy storage device using the nonaqueous electrolytic solution, and a specific trifluoromethylbenzene compound. There are provided a nonaqueous electrolytic solution of an electrolyte salt dissolved in a nonaqueous solvent, which comprises at least one halogenoalkylbenzene compound represented by the following general formula (I), an energy storage device using the nonaqueous electrolytic solution, and a specific trifluoromethylbenzene compound. (In the formula, Y 1 represents an alkoxycarbonyl group having from 2 to 8 carbon atoms, an alkenyloxycarbonyl group having from 3 to 9 carbon atoms, an alkynyloxycarbonyl group having from 4 to 9 carbon atoms, an aryloxycarbonyl group having from 7 to 12 carbon atoms, an alkanesulfonyl group having from 1 to 6 carbon atoms, or an arylsulfonyl group having from 6 to 12 carbon atoms; R X represents a halogenoalkyl group having from 1 to 4 carbon atoms; n indicates an integer of from 1 to 5. However, when Y 1 is an alkoxycarbonyl group having from 2 to 12 carbon atoms or an aryloxycarbonyl group having from 6 to 12 carbon atoms, the number of carbon atom of R X is 1. In the substituent represented by Y 1 , at least one hydrogen atom may be substituted with a halogen atom.)

  本发明旨在提供一种非水电解质溶液，能够增强广泛温度范围内的电化学特性，使用非水电解质溶液的储能装置以及一种特定的三氟甲基苯化合物。提供了一种电解质盐在非水溶剂中溶解的非水电解质溶液，其中包括至少一种由下述通式（I）表示的卤代烷基苯化合物，使用非水电解质溶液的储能装置以及一种特定的三氟甲基苯化合物。（在公式中，Y1表示具有2至8个碳原子的烷氧羰基基团，具有3至9个碳原子的烯烃氧羰基基团，具有4至9个碳原子的炔烃氧羰基基团，具有7至12个碳原子的芳基氧羰基基团，具有1至6个碳原子的烷基磺酰基团或具有6至12个碳原子的芳基磺酰基团；RX表示具有1至4个碳原子的卤代烷基团；n表示1至5的整数。但是，当Y1是具有2至12个碳原子的烷氧羰基基团或具有6至12个碳原子的芳基氧羰基基团时，RX的碳原子数为1。在Y1所表示的取代基中，至少有一个氢原子可以被卤素原子取代。）