Diphenyl-acetic acid 2-thioxo-2H-pyridin-1-yl ester | 114050-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Diphenyl-acetic acid 2-thioxo-2H-pyridin-1-yl ester
• 英文别名: (2-Sulfanylidenepyridin-1-yl) 2,2-diphenylacetate
• CAS: 114050-26-9
• 化学式: C₁₉H₁₅NO₂S
• 分子量: 321.4
• InChiKey: XERVLOPXWIMZOR-UHFFFAOYSA-N

物化性质

• 沸点：
  465.1±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  Diphenyl-acetic acid 2-thioxo-2H-pyridin-1-yl ester 以 环己烷 为溶剂， 生成 diphenylmethyl radical
  参考文献：
  名称：

  Exploratory studies of the photochemistry of N-hydroxypyridine-2-thione esters. Generation of excited radicals by laser flash photolysis and in a conventional fluorescence spectrometer

  摘要：

  DOI：

  10.1021/jo00306a025
• 作为产物：
  描述：

  二苯基乙酰氯 、 thallium(I) N-hydroxypyridine-2-thione 以 乙醚 为溶剂， 反应 0.5h， 生成 Diphenyl-acetic acid 2-thioxo-2H-pyridin-1-yl ester
  参考文献：
  名称：

  Photochemistry of N-Hydroxypyridine-2-thione Derivatives: Involvement of the 2-Pyridylthiyl Radical in the Radical Chain Reaction Mechanism

  摘要：

  The primary and subsequent photochemistry of four N-hydroxypyridine-2-thione esters has been investigated by laser flash photolysis (lambda(exc) = 355 nm). A simple, high-yield synthetic method is given for their preparation with high purity. UV irradiation of these ester compounds was shown to lead specifically to the formation of benzyl, diphenylmethyl, tert-butyl, and benzoyloxyl radicals in addition to the 2-pyridylthiyl radical. in all cases, the initial photoinduced nitrogen-oxygen bond cleavage was found to occur in high quantum yield (Phi(N-O) approximate to 0.5) The radical species generated by this process (2-pyridylthiyl radical and carbon-centered or oxygen-centered radicals) were characterized and their reactivity toward several radical scavengers has been studied. An efficient delayed depletion of the N-hydroxypyridine-2-thione esters was also observed, leading to overall bleaching quantum yields, (Phi(B1), close to unity. We have demonstrated that the delayed consumption of ground-state ester was due to the reaction of the 2-pyridylthiyl radical with its precursor, occurring with a rate constant, k(r), of 3-4 x 10(9) M(-1) s(-1). This reaction, hitherto never proposed, leads to the formation of 2,2'-dipyridyl disulfide and further release of propagating radicals.

  DOI：

  10.1021/ja00143a013

文献信息

• The invention of radical reactions
  作者：Derek H.R. Barton、Dominique Bridon、Isabel Fernandaz-Picot、Samir Z. Zard

  DOI：10.1016/s0040-4020(01)86878-2

  日期：1987.1

  Esters (mixed anhydrides) derived from aliphatic or alicyclic carboxylic acids (RCO2H) and thiohydroxamic acids or undergo a thermally or photochemically induced radical chain reaction to give sulphides with loss of carbon dioxide. On irradiation at low-temperature however, the chain reaction is essentially supressed. Under these conditions moderate to good yields of dimers R-R are obtained from primary

  衍生自脂肪族或脂环族羧酸（RCO 2 H）和硫代异羟肟酸的酯（混合酸酐），或经过热或光化学诱导的自由基链反应，生成硫化物，并减少二氧化碳的损失。然而，在低温下照射时，链反应基本上被抑制。在这些条件下，从伯酸获得中等至良好产率的二聚体RR。讨论了这些观察结果的机理和综合意义。
• Barton, Derek H.R.; Bridon, Dominique; Zard, Samir Z., Heterocycles, 1987, vol. 25, p. 449 - 462
  作者：Barton, Derek H.R.、Bridon, Dominique、Zard, Samir Z.

  DOI：——

  日期：——
• BOHNE, C.;BOCH, R.;SCAIANO, J. C., J. ORG. CHEM., 55,(1990) N9, C. 5414-5418
  作者：BOHNE, C.、BOCH, R.、SCAIANO, J. C.

  DOI：——

  日期：——
• BARTON, DEREK H. R.;BRIDON, DOMINIQUE;FERNANDEZ-PICOT, ISABEL;ZARD, SAMIR+, TETRAHEDRON, 43,(1987) N 12, 2733-2740
  作者：BARTON, DEREK H. R.、BRIDON, DOMINIQUE、FERNANDEZ-PICOT, ISABEL、ZARD, SAMIR+

  DOI：——

  日期：——