dithiocarbonic acid S-(1-dimethoxymethyl-2-oxo-propyl) ester O-ethyl ester | 1164111-60-7

• 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: dithiocarbonic acid S-(1-dimethoxymethyl-2-oxo-propyl) ester O-ethyl ester
• 英文别名: O-ethyl (1,1-dimethoxy-3-oxobutan-2-yl)sulfanylmethanethioate
• CAS: 1164111-60-7
• 化学式: C₉H₁₆O₄S₂
• 分子量: 252.356
• InChiKey: PXDSQTRPSANQEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid S-(1-dimethoxymethyl-2-oxo-propyl) ester O-ethyl ester 、 3-(4-chloro-phenyl)-2-methanesulfonyl-pent-4-enoic acid ethyl ester 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 7.25h， 以44%的产率得到(E)-6-dimethoxymethyl-4-(4-chloro-phenyl)-7-oxo-oct-2-enoic acid ethyl ester
  参考文献：
  名称：

  A Convergent Radical-Based Route to Biaryls

  摘要：

  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.

  DOI：

  10.1021/ol9010294

文献信息

• Tri- and Tetrasubstituted Functionalized Vinyl Sulfides by Radical Allylation
  作者：Laurent Debien、Marie-Gabrielle Braun、Béatrice Quiclet-Sire、Samir Z. Zard

  DOI：10.1021/ol403103u

  日期：2013.12.20

  2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition–elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates

  衍生自苯基乙烯基硫化物的2-氟吡啶基-6-氧基-前体与黄原酸酯生成的自由基通过加成-消除过程反应，从而以高收率提供了相应的乙烯基硫化物。这种会聚方法操作简单，可直接合成难以获得的四取代乙烯基硫化物。乙烯基硫化物在与N-酰基阳离子发生高度立体选择性的反应中，被用作更坚固的烯醇醚替代物，从而导致含氮多环结构。
• A convergent, modular access to complex amines
  作者：Béatrice Quiclet-Sire、Guillaume Revol、Samir Z. Zard

  DOI：10.1016/j.tet.2010.05.107

  日期：2010.8

  Various xanthates can be added to N-vinyl phthalimide with little formation of oligomers, if the xanthate is used in excess and the medium slightly diluted. The adduct xanthates thus obtained can in turn undergo radical additions to numerous olefins, providing a convergent and modular access to densely functionalized amines. (C) 2010 Elsevier Ltd. All rights reserved.
• Modular Approach to Substituted Boc-Protected 4-(Aminomethyl)pyrroles
  作者：Songzhe Han、Samir Z. Zard

  DOI：10.1021/ol500544u

  日期：2014.4.4

  The radical addition of various alpha-xanthyl ketones to Boc-protected azetine gives adducts which, when treated with ammonia or primary amines, furnish 2,4-disubstituted, 2,3,4-trisubstituted, and polycyclic pyrroles having a protected aminomethyl group at position 4. An unusual ring-opening was observed in the case of a cyclobutanone precursor.