ethyl [1-(tert-butoxycarbonylamino)-2,2,2-trifluoro-ethyl]sulfanylmethanethioate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: ethyl [1-(tert-butoxycarbonylamino)-2,2,2-trifluoro-ethyl]sulfanylmethanethioate
• 英文别名: dithiocarbonic acid (1-tert-butoxycarbonylamino-2,2,2-trifluoroethyl) ester ethyl ester；O-ethyl [2,2,2-trifluoro-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]sulfanylmethanethioate
• 化学式: C₁₀H₁₆F₃NO₃S₂
• 分子量: 319.369
• InChiKey: WZODWVBLACDICB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl [1-(tert-butoxycarbonylamino)-2,2,2-trifluoro-ethyl]sulfanylmethanethioate 、 吲哚-3-甲酸甲酯 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 以41%的产率得到methyl 2-(1-((tert-butoxycarbonyl)amino)-2,2,2-trifluoroethyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  Introduction of Trifluoroethylamine as Amide Isostere by C–H Functionalization of Heteroarenes

  摘要：

  A direct and efficient introduction of a trifluoroethylamine motif into various heteroaromatic structures, using a readily available xanthate S[1-(N-acetylamino)-2,2,2-trifluoroethy1]-O-ethyl dithiocarbonate (5), is reported. Medicinally relevant trifluoroethylaminated heteroarenes containing a wide range of functional groups were successfully synthesized under mild conditions. This amide isostere could be introduced into both electron-rich and-poor heteroarenes to give the desired products in one step. The beneficial effect of camphorsulfonic acid (CSA) was also demonstrated with electron-deficient heteroarenes.

  DOI：

  10.1021/acs.orglett.7b01880
• 作为产物：
  描述：

  氨基甲酸叔丁酯 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 乙醇 、 正庚烷 为溶剂， 反应 3.0h， 生成 ethyl [1-(tert-butoxycarbonylamino)-2,2,2-trifluoro-ethyl]sulfanylmethanethioate
  参考文献：
  名称：

  α-氨基三氟甲基黄原酸盐：一类新型 RAFT/MADIX 试剂

  摘要：

  长期以来，黄原酸盐一直被描述为苯乙烯聚合的不良 RAFT/MADIX 试剂。通过测定黄原酸盐的链转移常数，该工作证明了一系列新的α-酰胺基三氟甲基黄原酸盐的离去基团具有有益的俘获取代基效应，其中三氟乙酰基的效果最好。使用 SEC 峰分辨率方法，以 Cex = 2.7（增加 3-4 倍）定量确定先前观察到的 O-三氟乙基与 O-乙基对应物的 Z 基团活化。这项研究进一步证实了三氟甲基取代基的有利掺入可以在自由基链转移过程中激活黄原酸盐，并有助于确定迄今为止报道的用于苯乙烯 RAFT/MADIX 聚合的最具反应性的黄原酸盐。

  DOI：

  10.3390/molecules29102174

文献信息

• Novel compounds comprising a thiocarbonyl-sulfanyl group, which can be used for the radical synthesis of-alpha-perfluoroalkylamines
  申请人：Zard Samir

  公开号：US20060122404A1

  公开（公告）日：2006-06-08

  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).

  该发明涉及具有通式（I）的化合物，其制备方法及在有机自由基合成中的用途。该发明还涉及具有通式（II）的化合物，其制备方法以及制备具有通式（VIII）的化合物的方法。
• 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
• US7820831B2
  申请人：——

  公开号：US7820831B2

  公开（公告）日：2010-10-26
• Introduction of Trifluoroethylamine as Amide Isostere by C–H Functionalization of Heteroarenes
  作者：Marie-Gabrielle Braun、Georgette Castanedo、Ling Qin、Patrick Salvo、Samir Z. Zard

  DOI：10.1021/acs.orglett.7b01880

  日期：2017.8.4

  A direct and efficient introduction of a trifluoroethylamine motif into various heteroaromatic structures, using a readily available xanthate S[1-(N-acetylamino)-2,2,2-trifluoroethy1]-O-ethyl dithiocarbonate (5), is reported. Medicinally relevant trifluoroethylaminated heteroarenes containing a wide range of functional groups were successfully synthesized under mild conditions. This amide isostere could be introduced into both electron-rich and-poor heteroarenes to give the desired products in one step. The beneficial effect of camphorsulfonic acid (CSA) was also demonstrated with electron-deficient heteroarenes.