O-octadecyl S-(trifluoromethyl)carbonothioate

• 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: O-octadecyl S-(trifluoromethyl)carbonothioate
• 英文别名: O-octadecyl-S-trifluorothiol carbonate；Octadecyl trifluoromethylsulfanylformate；octadecyl trifluoromethylsulfanylformate
• 化学式: C₂₀H₃₇F₃O₂S
• 分子量: 398.574
• InChiKey: RLKRQGAFNSCYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-octadecyl S-(trifluoromethyl)carbonothioate 、 2-溴-1-间甲苯-乙酮 在 四氢吡咯 、 potassium fluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以86%的产率得到1-(m-tolyl)-2-((trifluoromethyl)thio)ethanone
  参考文献：
  名称：

  A Convenient Metal-Free Reagent for the Generation and Capture of Trifluoromethanethiol

  摘要：

  0-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium 0-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with alpha-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

  DOI：

  10.1021/ol403038f
• 作为产物：
  描述：

  硬脂醇 在 咪唑 、 氧气 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 环己烷 、 丙酮 、 mineral oil 为溶剂， 反应 24.83h， 生成 O-octadecyl S-(trifluoromethyl)carbonothioate
  参考文献：
  名称：

  A Convenient Metal-Free Reagent for the Generation and Capture of Trifluoromethanethiol

  摘要：

  0-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium 0-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with alpha-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

  DOI：

  10.1021/ol403038f

文献信息

• Tertiary Amine-Catalyzed Difluoromethylthiolation of Morita-Baylis-Hillman Carbonates of Isatins with Zard's Trifluoromethylthiolation Reagent
  作者：Xing Fan、Haibin Yang、Min Shi

  DOI：10.1002/adsc.201600954

  日期：2017.1.4

  tertiary amine‐catalyzed [3+2] annulation between Morita–Baylis–Hillman (MBH) carbonates derived from isatins with thiocarbonyl fluoride (F2C=S) in situ generated from Zard's reagent proceeds smoothly under mild conditions, affording difluoromethylthiolated spirocyclic oxindoles in good to excellent yields. Moreover, the asymmetric variant could be realized with a modified Cinchona alkaloid, giving the

  在本文中，我们报道了一种新的叔胺催化的[3 + 2]环化反应，该反应是由Isards衍生的Morita–Baylis–Hillman（MBH）碳酸酯与异硫氰酸羰基氟化物（F 2 C = S）从Zard试剂原位生成的在温和的条件下，以良好或优异的收率得到二氟甲基硫醇化的螺环羟吲哚。此外，可以用修饰的金鸡纳生物碱实现不对称变体，从而以良好的对映体选择性以及良好的产率获得所需的环状加合物。
• Regio- and Stereocontrolled Nucleophilic Trifluoromethylthiolation of Morita–Baylis–Hillman Carbonates
  作者：Dominique Cahard、Xiaoyang Dai

  DOI：10.1055/s-0034-1379162

  日期：——

  Reactions of Morita-Baylis-Hillman carbonates with metal-free sources of trifluoromethylthio anion have been studied. The combination of CF3SiMe3/S-8/KF/DMF gave the primary allylic SCF3 products through apparent S(N)2' reaction whereas the use of Zard's reagent, CF3SCO2C18H37, allowed us to intercept the fleeting secondary allylic SCF3 product.
• A Convenient Metal-Free Reagent for the Generation and Capture of Trifluoromethanethiol
  作者：Shi-Guang Li、Samir Z. Zard

  DOI：10.1021/ol403038f

  日期：2013.11.15

  0-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium 0-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with alpha-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.