dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester
• 英文别名: dithiocarbonic acid S-[2-(2,4-difluorophenyl)-2-oxo-ethyl] ester O-ethyl ester；O-ethyl [2-(2,4-difluorophenyl)-2-oxoethyl]sulfanylmethanethioate
• 化学式: C₁₁H₁₀F₂O₂S₂
• 分子量: 276.328
• InChiKey: NCZKJZQWIREAMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 4-(3-(2,4-difluorophenyl)-3-oxopropyl)-4-methyl-1,3-dithian-2-one
  参考文献：
  名称：

  Modular Routes to 1,3-Dithian-2-ones and 1,2-Dithiolanes

  摘要：

  DOI：

  10.1021/acs.orglett.2c02214
• 作为产物：
  描述：

  2-氯-2',4'-二氟苯乙酮 、 potassium ethyl xanthogenate 以 丙酮 为溶剂， 以93%的产率得到dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester
  参考文献：
  名称：

  A divergent approach to highly substituted benzothiepinones and to 2,3-dihydrothieno[2,3-b]thiopyran-4-ones

  摘要：

  The radical addition-transfer of S-(2-fluoro-phenacyl)xanthates can be used to construct rapidly benzothiepinones, including libraries of complex aza-bridged derivatives, and highly functionalized 2,3-dihydrothieno[2,3-b]thiopyran-4-ones. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.006
• 作为试剂：
  描述：

  1-cyclopropyl-2-methyl-2-phenylpropan-1-one 在 过氧化双月桂酰 、 叔丁基锂 、 dithiocarbonic acid S-[2-(2,4-difluoro-phenyl)-2-oxo-ethyl] ester O-ethyl ester 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 3.17h， 生成 2,3-二甲基-2,3-二苯基丁烷
  参考文献：
  名称：

  从自由基断裂中极性效应的显着表现到高度官能化酮的收敛合成

  摘要：

  报道了一种新的自由基加成/CC 键断裂过程。衍生自 2-甲基-2-苯基丙醛的乙烯基甲醇与由黄原酸酯产生的自由基反应生成相应的酮。自由基裂解反应在温和的条件下进行，收率良好至高，并且存在未保护的甲醇。使用这种方法可以很容易地获得高度官能化的 1,5-二酮和吡啶。

  DOI：

  10.1021/ja400831w

文献信息

• A radical exchange process: synthesis of bicyclo[1.1.1]pentane derivatives of xanthates
  作者：Saroj Kumar Rout、Gilles Marghem、Junjie Lan、Tom Leyssens、Olivier Riant

  DOI：10.1039/c9cc07610g

  日期：——

  Bicyclo[1.1.1]pentane (BCP) replacement as a bioisostere in drug molecules has an influence on their permeability, aqueous solubility and in vitro metabolic stability. Thus, the chemical installation of the BCP unit into a chemical entity remains a significant challenge from a synthetic point of view. Here, we have presented a new approach for the installation of the BCP unit on the xanthate moiety

  双环[1.1.1]戊烷（BCP）替代物作为药物分子中的生物等排物，对其渗透性，水溶性和体外代谢稳定性都有影响。因此，从合成的角度来看，将BCP单元化学安装到化学实体中仍然是一项重大挑战。在这里，我们提出了一种通过自由基交换过程在黄药部分上安装BCP单元的新方法。
• A flexible strategy for the divergent modification of pleuromutilin
  作者：Eric Bacqué、François Pautrat、Samir Z. Zard

  DOI：10.1039/b206568a

  日期：——

  The complex antibacterial natural product, pleuromutilin, can be directly modified by the radical addition reaction of various xanthates to the unactivated terminal olefin present on C-12.

  复杂的抗菌天然产物普鲁莫缇林，可以通过不同黄硫酸盐与C-12上未活化的末端烯烃的自由基加成反应直接修饰。
• Allylic Alcohols as Radical Allylating Agents. An Overall Olefination of Aldehydes and Ketones
  作者：Nicolas Charrier、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ja802899m

  日期：2008.7.1

  2-Fluoroyridynl derivatives of allylic alcohols react with xanthates in the presence of lauroyl peroxide to give alkenes, often with high stereoselectivity. If the allylic alcohols are themselves derived from aldehydes or ketones, the overall process becomes a synthetic equivalent of the classical Witting and related olefination reactions.
• A Convergent Radical-Based Route to Biaryls
  作者：Béatrice Quiclet-Sire、Guillaume Revol、Samir Z. Zard

  DOI：10.1021/ol9010294

  日期：2009.7.2

  A route to biaryl-3-carboxylate esters involving a radical 1,2-aryl migration has been developed. This strategy hinges on the radical addition of xanthate 2 to olefin 1 causing a 1,2-aryl shift leading to alpha,beta-unsaturated ester 5, which is then converted into biaryl 10 by treatment with DBU under microwave heating.
• Flexible Routes to Thiophenes
  作者：Hélène Jullien、Béatrice Quiclet-Sire、Thomas Tétart、Samir Z. Zard

  DOI：10.1021/ol403310f

  日期：2014.1.3

  Three convergent routes to thiophenes are described, hinging on the radical addition of alpha-xanthyl ketones to ethyl vinyl sulfide or to vinyl pivalate. The latter route ultimately proved to be the most versatile and efficient (61-94%).