O-octadecyl S-(trifluoromethyl)carbonodithioate

• 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)carbonodithioate
• 英文别名: O-octadecyl trifluoromethylsulfanylmethanethioate
• 化学式: C₂₀H₃₇F₃OS₂
• 分子量: 414.64
• InChiKey: CJRBPWPZSUQBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 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：
  66.6
• 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)carbonodithioate 在 氧气 、 臭氧 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 octadecyl N,N-dimethylcarbamate
  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 、 sodium hydride 作用下， 以 四氢呋喃 、 环己烷 、 mineral oil 为溶剂， 反应 22.83h， 生成 O-octadecyl S-(trifluoromethyl)carbonodithioate
  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

• A Convergent Synthesis of Enantiopure Open-Chain, Cyclic, and Fluorinated α-Amino Acids
  作者：Shi-Guang Li、Fernando Portela-Cubillo、Samir Z. Zard

  DOI：10.1021/acs.orglett.6b00656

  日期：2016.4.15

  A radical based synthesis of a broad variety of protected enantiopure α-amino acids, including fluorinated derivatives, is described. The radical addition furnishes naturally latent mercapto-α-amino acids ideally equipped for native chemical ligation.

  描述了自由基保护的多种受保护的对映纯α-氨基酸（包括氟化衍生物）的合成。自由基的加成提供了天然潜伏的巯基-α-氨基酸，非常适合天然化学连接。
• Radical Fragment Coupling Route to Geminal Bis(boronates)
  作者：Qi Huang、Samir Z. Zard

  DOI：10.1021/acs.orglett.8b02235

  日期：2018.9.7

  atom abstraction and delivers a vast array of highly functional geminal bis(boronates). The ability to assemble geminal bis(boronates) bearing polar functional groups not readily obtained through existing methods is particularly noteworthy. This approach also opens up access to geminal bis(boronyl) cyclopropanes and geminal bis(boronyl) tetrahydroquinolines.

  将二硫代碳酸酯自由基加成到1,1-双（硼基）-3-丁烯和相关的烯烃中，不会造成碎片或氢原子抽象的复杂情况，并且可提供大量高功能双键双（硼酸酯）。通过现有方法不易获得的带有双极性基团的双（硼酸酯）双宝石的组装能力特别值得注意。这种方法也为双子双（硼烷基）环丙烷和双（双硼烷基）四氢喹啉提供了可能。
• Radical Instability in Aid of Efficiency: A Powerful Route to Highly Functional MIDA Boronates
  作者：Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/jacs.5b03893

  日期：2015.6.3

  The inability of the sp(3) boron in MIDA boronates to stabilize an adjacent radical makes possible the efficient addition of a wide array Of xanthates to vinyl MIDA boronate, leading to highly functionalized and diverse aliphatic organoboron structures. The lack of radical Stabilization also allows the exchange Of the Xanthate in the adducts with a bromine. In one case, the bromine was substituted to generate a cyclopropyl MIDA derivative.
• Carbon Radical Attack on a Pyrimidine Nitrogen. An Unusual Entry into Polycyclic Aminopyrimidones
  作者：Ling Qin、Zhibo Liu、Samir Z. Zard

  DOI：10.1021/ol501104h

  日期：2014.6.6

  Unprecedented examples of a synthetically useful radical ring closure onto a pyrimidine nitrogen leading to novel, highly functionalized bi- and tricyclic pyrimidone structures are reported. An unexpected hydrogen atom translocation prior to the cyclization step was observed in some cases.