dithiocarbonic acid S-(2,5-dioxo-pyrrolidin-1-ylmethyl) ester O-ethyl ester | 1042038-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dithiocarbonic acid S-(2,5-dioxo-pyrrolidin-1-ylmethyl) ester O-ethyl ester
• 英文别名: O-ethyl (2,5-dioxopyrrolidin-1-yl)methylsulfanylmethanethioate
• CAS: 1042038-98-1
• 化学式: C₈H₁₁NO₃S₂
• 分子量: 233.312
• InChiKey: WSSLMBXMNDFBEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dithiocarbonic acid S-(2,5-dioxo-pyrrolidin-1-ylmethyl) ester O-ethyl ester 、 N-(1-allylcyclopentyl)-4,6-dichloropyrimidin-2-amine 在 过氧化双月桂酰 作用下， 以 乙酸乙酯 为溶剂， 以67%的产率得到S-(1-(1-((4,6-dichloropyrimidin-2-yl)amino)cyclopentyl)-4-(2,5-dioxopyrrolidin-1-yl)butan-2-yl)-O-ethyl carbonodithioate
  参考文献：
  名称：

  Carbon Radical Attack on a Pyrimidine Nitrogen. An Unusual Entry into Polycyclic Aminopyrimidones

  摘要：

  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.

  DOI：

  10.1021/ol501104h
• 作为产物：
  描述：

  1-(2-bromomethyl)pyrrolidine-2,5-dione 、 potassium ethyl xanthogenate 以 丙酮 为溶剂， 以91%的产率得到dithiocarbonic acid S-(2,5-dioxo-pyrrolidin-1-ylmethyl) 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

• Xanthate-mediated intermolecular alkylation of pyrazines
  作者：Qi Huang、Ling Qin、Samir Z. Zard

  DOI：10.1016/j.tet.2018.08.040

  日期：2018.10

  An expedient approach for the intermolecular C-H functionalization of pyrazines and other heteroarenes by the radical chemistry of xanthates is reported. Incorporation of a multitude of functional alkyl groups onto these heteroarenes proceeds in good yield and good to excellent regioselectivity, leading to highly functionalized heteroaromatics.

  报道了通过黄药的自由基化学对吡嗪和其他杂芳烃进行分子间CH官能化的简便方法。在这些杂芳烃上并入大量官能烷基的产率高并且区域选择性好至极好，从而导致高度官能化的杂芳族化合物。
• 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。
• Degenerative xanthate transfer to olefins under visible-light photocatalysis
  作者：Atsushi Kaga、Xiangyang Wu、Joel Yi Jie Lim、Hirohito Hayashi、Yunpeng Lu、Edwin K L Yeow、Shunsuke Chiba

  DOI：10.3762/bjoc.14.283

  日期：——

  The degenerative transfer of xanthates to olefins is enabled by the iridium-based photocatalyst [IrdF(CF3)ppy}2(dtbbpy)](PF6) under blue LED light irradiation. Detailed mechanistic investigations through kinetics and photophysical studies revealed that the process operates under a radical chain mechanism, which is initiated through triplet-sensitization of xanthates by the long-lived triplet state

  在蓝色LED光照射下，铱基光催化剂[Ir dF（CF3）ppy} 2（dtbbpy）]（PF6）能够使黄原酸酯退化转化为烯烃。通过动力学和光物理研究进行的详细机械研究表明，该过程在自由基链机制下运行，该机制是通过铱基光催化剂的长寿命三重态通过对黄药的三重敏化而引发的。
• Radical <i>ipso</i>-Substitution of a Carbon–Fluorine Bond Leading to Fluoro-7-azaindolines and Fluoro-7-azaindoles
  作者：Zhibo Liu、Ling Qin、Samir Z. Zard

  DOI：10.1021/ol500985f

  日期：2014.5.16

  Rare examples of a synthetically useful radical ipso-substitution of a carbon–fluorine bond are reported, leading to highly functionalized 5,6-difluoro-7-azaindolines. An unexpected hydrogen atom translocation and fragmentation with loss of molecular nitrogen and formation of a nitrile were observed in the case of an N-benzyl-tetrazole derivative.

  报道了碳-氟键在合成上有用的自由基ipso取代的罕见例子，导致高度官能化的5,6-二氟-7-氮杂二氢吲哚。在N-苄基-四唑衍生物的情况下，观察到了意外的氢原子易位和断裂，并损失了分子氮并形成了腈。
• 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.