Difluor-S-phenyl-thioglykolsaeure-methylester | 22340-44-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Difluor-S-phenyl-thioglykolsaeure-methylester
• 英文别名: Methyl 2,2-difluoro-2-phenylsulfanylacetate
• CAS: 22340-44-9
• 化学式: C₉H₈F₂O₂S
• 分子量: 218.224
• InChiKey: ZFDXMOTVBCYYRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Difluor-S-phenyl-thioglykolsaeure-methylester 在 chromium(VI) oxide 、 盐酸 、 溶剂黄146 作用下， 生成 phenylsulfonyldifluoroacetic acid
  参考文献：
  名称：

  Yagupol'skii,L.M.; Korin'ko,V.A., Journal of general chemistry of the USSR, 1969, vol. 39, p. 186 - 189

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 二氟(苯基硫基)乙酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 生成 Difluor-S-phenyl-thioglykolsaeure-methylester
  参考文献：
  名称：

  Yagupol'skii,L.M.; Korin'ko,V.A., Journal of general chemistry of the USSR, 1969, vol. 39, p. 186 - 189

  摘要：

  DOI：

文献信息

• Placing CF ₂ in the Center: Major Physicochemical Changes Upon a Minor Structural Alteration in Gem‐Difunctional Compounds
  作者：Sigal Saphier、Shahaf Katalan、Guy Yacov、Anat Berliner、Orit Redy‐Keisar、Gil Fridkin、Lee Ghindes‐Azaria、Ishay Columbus、Alexander Pevzner、Eyal Drug、Hagit Prihed、Eytan Gershonov、Yoav Eichen、Shlomi Elias、Galit Parvari、Yossi Zafrani

  DOI：10.1002/chem.202202939

  日期：2023.2

  A large increase in lipophilicity is observed for CH2/CF2 replacement in the center of di-functional compounds. The increase, in the range of 0.6–1.4 units is for most cases, far above expected values. The effect is nearly additive, thus one can switch from a hydrophilic compound to a lipophilic one using a limited number of H/F exchanges. In this paper, the effect and its origins are explored.

  在双官能化合物的中心观察到 CH 2 /CF 2取代的亲脂性大幅增加。在大多数情况下，增加 0.6–1.4 个单位，远高于预期值。这种效果几乎是叠加的，因此可以使用有限次数的 H/F 交换从亲水性化合物转换为亲脂性化合物。在本文中，探讨了影响及其起源。
• Adsorption effects on the selective electrofluorination of α-(phenylthio)acetamides and α-(phenylthio)acetates in Et3N·3HF/CH3CN
  作者：V. Suryanarayanan、S. Chellammal、M. Noel

  DOI：10.1016/s0022-1139(98)00279-6

  日期：1999.1

  Cyclic voltammetric behaviour of alpha-(phenylthio)acetamides and alpha-(phenylthio)acetates were compared in CH3CN/tetrabutylammonium perchlorate (TBAP) and CH3CN/Et3N . 3HF to assess the influence of fluoride ion on the oxidative pathway. These studies support the Pummerer mechanistic pathway involving an initial attack at sulfur in selective electrofluorination (SEF). A linear correlation between the peak current values in cyclic voltammetry and overall synthetic yield in preparative electrolysis was obtained suggesting the importance of weak blocking or a reactive adsorption effect on the overall synthetic processes. Other factors influencing the adsorption and insulation of electrode surfaces during the SEF are also discussed. (C) 1999 Elsevier Science S.A. All rights reserved.