toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester | 13652-13-6

• 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: toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester
• 英文别名: 2,2,2-trifluoro-1-phenylethyl 4-methylbenzenesulfonate；1-phenyl-2,2,2-trifluoroethyl tosylate；2,2,2-Trifluoro-1-phenylethyl tosylate；2,2,2-Trifluoaethyl-1-phenylaethyl-p-toluolsulfonat；1-Phenyl-2,2,2-trifluoraethan-1-tosylat；2,2,2-Trifluoro-1-phenylethyl p-toluenesulfonate；(2,2,2-trifluoro-1-phenylethyl) 4-methylbenzenesulfonate
• CAS: 13652-13-6
• 化学式: C₁₅H₁₃F₃O₃S
• 分子量: 330.328
• InChiKey: ZQSPVDCJGDZANF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium phosphate 、 lithium aluminium tetrahydride 、 lithium hexamethyldisilazane 、 三环己基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 正己烷 为溶剂， 反应 14.92h， 生成 (2-氟-1-苯基乙烯基)苯
  参考文献：
  名称：

  Monofluorovinyl Tosylate: A Useful Building Block for the Synthesis of Terminal Vinyl Monofluorides via Suzuki−Miyaura Coupling

  摘要：

  Monofluorovinyl tosylate was developed as a practical vinyl fluoride building block to couple with a variety of arylboronic acids in the presence of a palladium catalyst. The high stereoselectivity of 2-aryl-1-fluoroethene derivatives was achieved. This approach is also applicable to the synthesis of 2,2-diaryl-1-fluoroethenes in good yields.

  DOI：

  10.1021/ol102645g
• 作为产物：
  描述：

  2,2,2-三氟苯乙酮 在 sodium hydroxide 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 toluene-4-sulfonic acid 2,2,2-trifluoro-1-phenyl-ethyl ester
  参考文献：
  名称：

  Solvolysis of 1-aryl-2,2,2-trifluoroethyl sulfonates. Kinetic and stereochemical effects in the generation of highly electron-deficient carbocations

  摘要：

  DOI：

  10.1021/ja00346a039

文献信息

• Profiling Sulfonate Ester Stability: Identification of Complementary Protecting Groups for Sulfonates
  作者：Stephen C. Miller

  DOI：10.1021/jo1007338

  日期：2010.7.2

  molecules such as dyes. This modification is usually performed as a final step, since sulfonated molecules are poorly soluble in most organic solvents, which complicates their synthesis and purification. This work compares the intrinsic lability of different sulfonate esters, identifying new sulfonate protecting groups and mild, selective cleavage conditions.

  磺化因其赋予疏水性分子（如染料）水溶性的能力而备受推崇。这种修饰通常作为最后一步进行，因为磺化分子在大多数有机溶剂中的溶解性很差，这使得它们的合成和纯化变得复杂。这项工作比较了不同磺酸酯的固有不稳定性，确定了新的磺酸酯保护基团和温和的选择性裂解条件。
• Cross‐Electrophile Coupling between Aryl/Vinyl Triflates and Vinyl Tosylates for the Synthesis of <i>gem</i> ‐Difluoroalkenes via Ni/Pd Cooperative Catalysis
  作者：Baojian Xiong、Yue Li、Jinyu Zhang、Jiangjun Liu、Xuemei Zhang、Zhong Lian

  DOI：10.1002/adsc.202101388

  日期：2022.3

  A dual nickel-/palladium-catalyzed direct gem-difluorovinylation of readily available aryl/vinyl triflates with substituted gem-difluorovinyl tosylates is presented. This protocol affords various diaryldifluoroalkene, arylalkyldifluoroalkene and 1,1-difluoro-2-substituted-1,3-dienes under mild reaction conditions with excellent functional group compatibility, and provides a potential pathway to the

  提出了一种双镍-/钯催化的直接偕二氟乙烯基化方法，使容易获得的芳基/乙烯基三氟甲磺酸酯与取代的偕二氟乙烯基甲苯磺酸酯发生反应。该方案在温和的反应条件下提供了各种二芳基二氟烯烃、芳烷基二氟烯烃和 1,1-二氟-2-取代-1,3-二烯，具有优异的官能团相容性，为复杂生物活性分子的后期功能化提供了潜在途径。
• Synthesis of α-(trifluoromethyl)phenylacetonitrile. Anomalous reactions of α-tosyloxy-α-(trifluoromethyl)phenylacetonitrile with sodium borohydride
  作者：Gábor Németh、László Poszácz、Dániel Bózsing、Gyula Simig

  DOI：10.1016/0022-1139(96)03433-1

  日期：1996.5

  The hitherto unknown α-(trifluoromethyl)phenylacetonitrile has been synthesized by reduction of the cyanohydrin of α,α,α-trifluoroacetophenone. Sodium borohydride reduction of the corresponding cyanohydrin tosylate resulted in reductive decyanation in dimethyl sulphoxide and in reduction of the nitrile group in t-butanol.

  迄今未知的α-（三氟甲基）苯基乙腈是通过还原α，α，α-三氟苯乙酮的氰醇合成的。相应的氰醇甲苯磺酸盐的硼氢化钠还原导致二甲基亚砜中的还原性脱氰作用和叔丁醇中的腈基还原。
• Proton-transfer reactions. II. Effects of internal return on reactivity difference between alkoxide-promoted eliminations in tert-butyl alcohol and ethyl alcohol
  作者：H. F. Koch、W. Tumas、R. Knoll

  DOI：10.1021/ja00408a024

  日期：1981.9
• Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A., Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 317 - 324
  作者：Dneprovskii, A. S.、Eliseenkov, E. V.、Mil'tsov, S. A.

  DOI：——

  日期：——