2,2-dimethylpropionic acid 2-thioxo-2H-pyridin-1-yl ester | 89025-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,2-dimethylpropionic acid 2-thioxo-2H-pyridin-1-yl ester
• 英文别名: 2(1H)-Pyridinethione, 1-(2,2-dimethyl-1-oxopropoxy)-；(2-sulfanylidenepyridin-1-yl) 2,2-dimethylpropanoate
• CAS: 89025-50-3
• 化学式: C₁₀H₁₃NO₂S
• 分子量: 211.285
• InChiKey: YZAFBRPJCHIDPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethylpropionic acid 2-thioxo-2H-pyridin-1-yl ester 在 四氯化碳 作用下， 以 氘代氯仿 为溶剂， 生成 氯代叔丁烷
  参考文献：
  名称：

  Quantum yields in the photochemically induced radical chemistry of acyl derivatives of thiohydroxamic acids

  摘要：

  Acyl derivatives of N-hydroxyquinazoline-4-thiones are a novel source of disciplined carbon radicals. Quantum yield determination reveals that photolysis of these compounds initiates radical chains, resulting in quantum yields up to PHI = 60. Comparative studies with acyl derivatives of N-hydroxy-2-thiopyridone show that the quinazoline derivatives are more light-sensitive than the thiopyridone compounds. The carbon radicals thus formed from the former can be trapped selectively, without the formation of rearranged products (i.e. without the competition of the radicophilic thiocarbonyl group of the starting material with the radical trap).

  DOI：

  10.1021/ja00018a034
• 作为产物：
  描述：

  三甲基乙酸 在 吡啶 、 草酰氯 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.5h， 生成 2,2-dimethylpropionic acid 2-thioxo-2H-pyridin-1-yl ester
  参考文献：
  名称：

  Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones.

  摘要：

  Irradiation of O-acyl derivatives 1 of N-hydroxy- 2-thiopyridone with visible light in the presence of phenyl vinyl sulphone or vinyl triphenylphosphonium bromide leads to the corresponding adducts 8 and 9 which can undergo a wide variety of further transformations.

  DOI：

  10.1016/s0040-4020(01)96163-0

文献信息

• Stereoselective radical reactions with chiral acrylamides and methacrylamides
  作者：Bernd Glese、Ursula Hoffmann、Martin Roth、Andreas Velt、Caroline Wyss、Margaretha Zehnder、Hendrik Zipse

  DOI：10.1016/s0040-4039(00)60437-9

  日期：1993.4

  Stereoselective radical reactions are observed with chiral methacrylamides 3 and 7. although the π-systems are twisted to a considerable extent.

  观察到手性甲基丙烯酰胺3和7的立体选择性自由基反应。尽管π系统在相当大的程度上扭曲了。
• Unified Synthesis of Quinone Sesquiterpenes Based on a Radical Decarboxylation and Quinone Addition Reaction
  作者：Taotao Ling、Erwan Poupon、Erik J. Rueden、Sun H. Kim、Emmanuel A. Theodorakis

  DOI：10.1021/ja027517q

  日期：2002.10.1

  several quinone sesquiterpenes is described herein. Essential to this strategy is a novel radical addition reaction that permits the attachment of a fully substituted bicyclic core 16 to a variably substituted quinone 10. The addition product 15 can be further functionalized, giving access to natural products with a high degree of oxygenation at the quinone unit. The quinone addition reaction is characterized

  本文描述了几种醌倍半萜的统一合成。该策略的关键是一种新的自由基加成反应，它允许将完全取代的双环核 16 连接到可变取代的醌 10。加成产物 15 可以进一步官能化，从而获得具有高度氧化的天然产物醌单位。醌加成反应的特点是优异的化学选择性，仅发生在共轭和未取代的双键上，区域选择性受到位于醌环上的杂原子的共振效应的强烈影响。这些特征已成功应用于阿瓦罗 (1)、阿瓦隆 (2)、甲氧阿瓦隆 (4、5)、伊马醌 (6) 和 smenospongidine (7) 的合成，从而证明了这种新方法的合成价值。
• New and improved methods for the radical decarboxylation of acids
  作者：Derek H. R. Barton、David Crich、William B. Motherwell

  DOI：10.1039/c39830000939

  日期：——

  Carboxylic acid esters derived from N-hydroxypyridine-2-thione undergo efficient radical chain decarboxylation to the corresponding nor-alkane on treatment with either tri-n-butylstannane or t-butylmercaptan; in the absence of these hydrogen atom donors a smooth decarboxylative rearrangement giving noralkyl 2-pyridyl sulphides is observed.

  在用三正丁基锡烷或叔丁基硫醇处理时，衍生自N-羟基吡啶-2-硫酮的羧酸酯进行有效的自由基链脱羧成相应的正构烷烃。在没有这些氢原子供体的情况下，观察到平滑的脱羧重排，给出了正烷基2-吡啶基硫化物。
• Radical addition to vinylphosphine oxides: 1,2-stereoinduction of phosphorus stercogcnic centre
  作者：Alberto Brandi、Stefano Cicchi、Andrea Goti、K. Michal Pietrusiewiez

  DOI：10.1016/s0040-4039(00)79740-1

  日期：1991.7

  AIBN havebeentrapped by diphenylvinylphosphine oxide 2 giving the addition products 6–8 in high yields. Free radical addition to 2 employing the Barton methodology gave lower yields. The use of chiral (racemic:) vinylphosphine oxides allowed a stereoselective radical addition with a diastercomeric ratio as high as 9:1 for mesitylmethylvinylphosphine oxide 1.

  在AIBN存在下，卤化物3-5与Bu 3 SnH的反应衍生出的碳偏静基团已被二苯基乙烯基氧化膦2截留，从而以高收率得到加成产物6-8。采用Barton方法向2中添加自由基的产率较低。使用手性（外消旋:) vinylphosphine氧化物的所允许的立体选择性基加以作为9 diastercomeric比率高达：1 mesitylmethylvinylphosphine氧化物1。
• The invention of radical reactions. Part XXXVIII. Homologation of car☐ylic acids with acrylamide and synthetic studies of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and its 4-epimer
  作者：Derek H.R. Barton、Wansheng Liu

  DOI：10.1016/s0040-4020(97)00543-7

  日期：1997.8

  Alkyl radicals generated from O-acyl derivatives of N-hydroxy-2-thiopyridone added onto acrylamide at room temperature to form crystalline 2-(2-pyridylsulfanyl)-car☐amides. Desulfurization of the latter by nickel boride at room temperature afforded primary amides in quantitative yield. 3-Deoxy-D-arabino-2-heptulosonic acid (DAH), its 4-epimer, and their derivatives were effectively synthesized from

  由N-羟基-2-硫代吡啶酮的O-酰基衍生物产生的烷基在室温下加到丙烯酰胺上，形成结晶的2-（2-吡啶基硫烷基）-car☐酰胺。在室温下通过硼化镍将后者脱硫，以定量收率得到伯酰胺。通过类似的自由基化学方法，从商业D-核糖内酯有效合成了3-Deoxy-D-阿拉伯糖-2-庚基磺酸（DAH），其4-表位及其衍生物。