dimethyl 4-chloro-2-[(ethoxymethanethioyl)sulfanyl]-5,5,5-trifluoropentane-1-phosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl 4-chloro-2-[(ethoxymethanethioyl)sulfanyl]-5,5,5-trifluoropentane-1-phosphonate
• 英文别名: [4-chloro-2-ethoxythiocarbonylsulphanyl-5,5,5-trifluoro-pentyl]-dimethyl phosphonate；2-(Ethoxycarbonothioylthio)-4-chloro-5,5,5-trifluoropentylphosphonic acid dimethyl ester；O-ethyl (4-chloro-1-dimethoxyphosphoryl-5,5,5-trifluoropentan-2-yl)sulfanylmethanethioate
• 化学式: C₁₀H₁₇ClF₃O₄PS₂
• 分子量: 388.797
• InChiKey: LJLSICSZDNFKAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl 4-chloro-2-[(ethoxymethanethioyl)sulfanyl]-5,5,5-trifluoropentane-1-phosphonate 在 偶氮二异丁腈 、 次磷酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以93%的产率得到dimethyl (4-chloro-5,5,5-trifluoropentyl)phosphonate
  参考文献：
  名称：

  A convergent, modular access to α-chloro-trifluoromethyl derivatives and to 1,1-difluoroalkenes

  摘要：

  An efficient protocol for the preparation of S-(1-chloro-2,2,2-trifluoroethyl)-O-ethyl xanthate is reported. This reagent serves as a versatile precursor of highly functionalized gem-difluoroalkenes through various inter- and intramolecular radical reactions and subsequent reduction with activated magnesium metal. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.021
• 作为产物：
  描述：

  S-(1-hydroxy-2,2,2-trifluoro-ethyl)-O-ethyl dithiocarbonate 在 过氧化双月桂酰 、 五氯化磷 作用下， 以 乙酸乙酯 、 正戊烷 为溶剂， 反应 2.5h， 生成 dimethyl 4-chloro-2-[(ethoxymethanethioyl)sulfanyl]-5,5,5-trifluoropentane-1-phosphonate
  参考文献：
  名称：

  A convergent, modular access to α-chloro-trifluoromethyl derivatives and to 1,1-difluoroalkenes

  摘要：

  An efficient protocol for the preparation of S-(1-chloro-2,2,2-trifluoroethyl)-O-ethyl xanthate is reported. This reagent serves as a versatile precursor of highly functionalized gem-difluoroalkenes through various inter- and intramolecular radical reactions and subsequent reduction with activated magnesium metal. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.021

文献信息

• A XANTHATE-TRANSFER APPROACH TO a-TRIFLUOROMETHYLAMINES
  作者：Gagosz, Fabien、Zard, Samir Z.、Laurich, Daniel、Fürstner, Alois

  DOI：10.15227/orgsyn.084.0032

  日期：——
• A direct approach to α-hydroxy and α-chloro trifluoromethyl derivatives
  作者：Lucie Tournier、Samir Z. Zard

  DOI：10.1016/j.tetlet.2004.11.086

  日期：2005.1

  S-1-Acyloxy-2,2,2-trifluoroethyl and S-1-chloro-2,2,2-trifluoroethyl dithiocarbonates add efficiently to various functionalised olefins to give the corresponding adducts via a radical chain reaction initiated by a small amount of lauroyl peroxide. (C) 2004 Elsevier Ltd. All rights reserved.
• NOUVEAUX COMPOSES COMPRENANT UN GROUPEMENT THIOCARBONYLSULFANYLE UTILES POUR LA SYNTHESE DE COMPOSES ALPHA-PERFLUOROALKYLAMINES PAR VOIE RADICALAIRE
  申请人：Centre National de la Recherche Scientifique

  公开号：EP1539688B1

  公开（公告）日：2016-08-10
• NOVEL COMPOUNDS COMPRISING A THIOCARBONYL-SULFANYL GROUP WHICH CAN BE USED FOR THE RADICAL SYNTHESIS OF ALPHA-PERFLUOROALKYLAMINE COMPOUNDS
  申请人：Zard Samir

  公开号：US20080306281A1

  公开（公告）日：2008-12-11

  The invention relates to compounds having the general formula (I), the method of preparation thereof and the use thereof in organic radical synthesis. The invention also relates to compounds having the formula (II), the method of preparation thereof and a method for preparing compounds having the formula (VIII).
• US7423161B2
  申请人：——

  公开号：US7423161B2

  公开（公告）日：2008-09-09