ethyl 2-(p-chlorophenylthio)-2-fluoroacetate | 129600-91-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-(p-chlorophenylthio)-2-fluoroacetate
• 英文别名: Ethyl 2-(4-chlorophenyl)sulfanyl-2-fluoroacetate
• CAS: 129600-91-5
• 化学式: C₁₀H₁₀ClFO₂S
• 分子量: 248.706
• InChiKey: CUGXDLULFMMDQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(p-chlorophenylthio)-2-fluoroacetate 在 氢氟酸 、 iodine pentafluoride 、 三乙胺 作用下， 反应 24.0h， 以75%的产率得到ethyl 2-((4-chlorophenyl)thio)-2,2-difluoroacetate
  参考文献：
  名称：

  Fluorination of Sulfides Using IF₅–Et₃N–3HF

  摘要：

  利用新型氟化试剂 IF5-Et3N-3HF 实现了硫化物的单氟化和二氟化。该试剂适用于具有各种夺电子基团的底物，如酯、酰胺、酮、腈、砜或三氟甲基。由于 IF5 上使用了一个以上的氟原子，因此即使进行二氟化反应，也无需过量使用该试剂。

  DOI：

  10.1246/bcsj.75.1597
• 作为产物：
  描述：

  2-[(4-氯苯基)硫代]乙酸乙酯 在 4-碘苯甲醚 、 triethylamine tris(hydrogen fluoride) 作用下， 生成 ethyl 2-(p-chlorophenylthio)-2-fluoroacetate
  参考文献：
  名称：

  Electrochemistry of Hypervalent Compounds. 6. Selective α-Fluorination of Sulfides Using Electrogenerated Hypervalentp-Methoxyiodobenzene Difluoride¹

  摘要：

  AbstractAnodically generated hypervalent p‐methoxyiodobenezene difluoride reacted with α‐(ary]thio)‐ and α‐(benzylthio)acetates, and α‐(phenylthio)acetophenone to provide the corresponding fluorinated compounds. In ail cases, a fluorine atom was introduced exclusively α to the ester or benzoyl group.

  DOI：

  10.1002/jccs.199800022

文献信息

• Ethyl phenylsulfinyl fluoroacetate, a new and versatile reagent for the preparation of α-fluoro-α,β-unsaturated carboxylic acid esters
  作者：Thomas Allmendinger

  DOI：10.1016/s0040-4020(01)80956-x

  日期：1991.1

  The title compound 2 can be alkylated with a wide range of alkyl halides and Michael acceptors. Subsequent thermal elimination of phenyl sulfinic acid 3 leads to α-fluoro-α,β-unsaturated ethyl carboxylates 5 and 10, an important class of intermediates for fluorine containing biologically active compounds.

  标题化合物2可以用多种烷基卤化物和迈克尔受体烷基化。随后热消除苯基亚磺酸3会导致α-氟代-α，β-不饱和羧酸乙酯5和10，这是含氟生物活性化合物的重要中间体。
• Electrolytic Partial Fluorination of Organic Compounds. 17. Regiospecific Anodic Fluorination of Sulfides Bearing Electron-Withdrawing Substituents at the Position .alpha. to the Sulfur Atom
  作者：Toshio Fuchigami、Moriyasu Shimojo、Akinori Konno

  DOI：10.1021/jo00116a037

  日期：1995.6

  Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.
• PROCESSES FOR THE PRODUCTION OF FLUORINATED ORGANIC COMPOUNDS AND FLUORINATING AGENTS
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：EP1304316B1

  公开（公告）日：2011-08-10
• US7311890B2
  申请人：——

  公开号：US7311890B2

  公开（公告）日：2007-12-25
• Fluorination of Sulfides Using IF₅–Et₃N–3HF
  作者：Shinichi Ayuba、Norihiko Yoneda、Tsuyoshi Fukuhara、Shoji Hara

  DOI：10.1246/bcsj.75.1597

  日期：2002.7

  Mono- and difluorinations of sulfides were achieved using a novel fluorinating reagent, IF5–Et3N–3HF. The reagent is applicable for substrates having various electron-withdrawing groups, such as an ester, amide, ketone, nitrile, sulfone, or trifluoromethyl. Because more than one fluorine atom on IF5 is used, a large excess amount of the reagent is not necessary, even for the difluorination reaction.

  利用新型氟化试剂 IF5-Et3N-3HF 实现了硫化物的单氟化和二氟化。该试剂适用于具有各种夺电子基团的底物，如酯、酰胺、酮、腈、砜或三氟甲基。由于 IF5 上使用了一个以上的氟原子，因此即使进行二氟化反应，也无需过量使用该试剂。