dithiocarbonic acid S-[3-cyano-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-propyl] ester O-ethyl ester | 1042038-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: dithiocarbonic acid S-[3-cyano-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-propyl] ester O-ethyl ester
• 英文别名: S-3-cyano-1-(1,3-dioxoisoindolin-2-yl)-3-methylbutyl-O-ethyl carbonodithioate；O-ethyl [3-cyano-1-(1,3-dioxoisoindol-2-yl)-3-methylbutyl]sulfanylmethanethioate
• CAS: 1042038-96-9
• 化学式: C₁₇H₁₈N₂O₃S₂
• 分子量: 362.474
• InChiKey: UECNHXKQJZTNNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碳酸亚乙烯酯 、 dithiocarbonic acid S-[3-cyano-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-propyl] ester O-ethyl ester 在 过氧化双月桂酰 作用下， 以 乙酸乙酯 为溶剂， 以59%的产率得到S-{5-[3-Cyano-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-propyl]-2-oxo-[1,3]dioxolan-4-yl}-O-ethyl dithiocarbonate
  参考文献：
  名称：

  A convergent, modular access to complex amines

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.05.107
• 作为产物：
  描述：

  N-乙烯基邻苯亚胺 、 S-2-cyano-2-propyl O-ethyl xanthate 在 过氧化双月桂酰 作用下， 以 乙酸乙酯 为溶剂， 以74%的产率得到dithiocarbonic acid S-[3-cyano-1-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-propyl] ester O-ethyl ester
  参考文献：
  名称：

  Radical Aminomethylation of Unactivated Alkenes

  摘要：

  S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

  DOI：

  10.1021/ol801162m

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。
• From a Remarkable Manifestation of Polar Effects in a Radical Fragmentation to the Convergent Synthesis of Highly Functionalized Ketones
  作者：Laurent Debien、Samir Z. Zard

  DOI：10.1021/ja400831w

  日期：2013.3.13

  A new radical addition/C-C bond fragmentation process is reported. Vinyl carbinols derived from 2-methyl-2-phenylpropanal react with radicals generated from xanthates to give the corresponding ketones. The radical cleavage reaction proceeds under mild conditions, in good to high yield, and in the presence of the unprotected carbinol. Highly functionalized 1,5-diketones and pyridines are readily available

  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。