2,5-diphenylisothiazol-3(2H)-one | 19983-35-8

• 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: 2,5-diphenylisothiazol-3(2H)-one
• 英文别名: 2,5-diphenyl-1,2-thiazol-3-one
• CAS: 19983-35-8
• 化学式: C₁₅H₁₁NOS
• 分子量: 253.324
• InChiKey: XCVACVOQHCBPPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-diphenylisothiazol-3(2H)-one 在 草酰氯 作用下， 生成 3-Chlor-2,5-diphenyl-isothiazolium-chlorid
  参考文献：
  名称：

  Faust,J., Zeitschrift fur Chemie, 1968, vol. 8, # 5, p. 170 - 171

  摘要：

  DOI：
• 作为产物：
  描述：

  phenylpropiolyl chloride 在 sodium hydroxide 、 碘 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 2,5-diphenylisothiazol-3(2H)-one
  参考文献：
  名称：

  2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction

  摘要：

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00053-3

文献信息

• A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles
  作者：Vikas Dwivedi、Manda Rajesh、Ravi Kumar、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1039/c7cc06081e

  日期：——

  A regio- and stereoselective thiocyanate addition to ynones is achieved using KSCN in AcOH at 70 °C. The reaction is extendable to ynals, ynesulfones, ynoic acids and ynoates. Adducts from ynones were readily transformed into thiazine-2-thione derivatives under slightly modified reaction conditions. In contrast, thiocyanated adducts from ynamides underwent an in situ decyanative amido cyclization towards

  使用KSCN在70°C的AcOH中，向炔酮中进行区域和立体选择性的硫氰酸酯加成反应。该反应可扩展至乙醛，乙炔砜，山药酸和山药。在稍微改变的反应条件下，来自炔酮的加合物很容易转化为噻嗪-2-硫酮衍生物。相反，来自酰胺的硫氰化加合物向异噻唑酮进行原位脱氰酰胺环化反应。这些事件均不需要任何过渡金属或催化剂，即可获得较高的合成价值。
• Copper‐Catalyzed Thioannulation of Propynamides with Sodium Sulfide for the Synthesis of Isothiazol‐3‐ones
  作者：Sui‐Qian Wang、Bo‐Lun Hu、Xing‐Guo Zhang

  DOI：10.1002/adsc.201801579

  日期：2019.3.15

  A method for the copper‐catalyzed thioannulation of propynamides with sodium sulfide was developed for the synthesis of isothiazol‐3‐ones. The reaction involves a nucleophilic addition and an intramolecular cross‐dehydrogenative coupling reaction. The thioannulation features the use of an inexpensive and odorless sulfur source and easily prepared propynamides with excellent functional group tolerance

  开发了一种用硫化钠铜催化的丙酰胺酰胺硫代环化反应的方法，用于合成异噻唑-3-酮。该反应涉及亲核加成和分子内交叉脱氢偶联反应。硫代环化的特点是使用廉价且无味的硫源，并易于制备具有出色的官能团耐受性的丙酰胺。
• 一种异噻唑-3-酮化合物的制备方法
  申请人：温州大学

  公开号：CN110066254B

  公开（公告）日：2021-03-19

  本发明公开了一种异噻唑‑3‑酮化合物及其制备方法，包括以下步骤：以2‑丙炔酰胺衍生物为底物，通过在底物中加入硫源、催化剂、氧化剂以及配体硫化钠作为硫源，整个反应在溶剂中进行，于80‑100℃氮气保护下搅拌反应10‑14小时；反应结束后，过滤反应液，并用饱和氯化钠溶液将滤液萃取两次，反萃一次，分离所得有机相用无水硫酸钠进行干燥后，再次进行过滤，并将滤液用旋转蒸发仪除去溶剂获得剩余物，通过硅胶柱对剩余物进行柱层分离，并经洗脱液进行淋洗，收集含有目标产物的流出液，合并流出液并经过真空浓缩除去溶剂获得目标产物。本发明具有原料简单易得，制备工艺新颖、简单、污染少、耗能低、产率高的优点。
• 2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction
  作者：Stephen W. Wright、Joseph J. Petraitis、Bruce Freimark、John V. Giannaras、Michael A. Pratta、Susan R. Sherk、Jean M. Williams、Ronald L. Magolda、Elizabeth C. Arner

  DOI：10.1016/0968-0896(96)00053-3

  日期：1996.6

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd
• Faust,J., Zeitschrift fur Chemie, 1968, vol. 8, # 5, p. 170 - 171
  作者：Faust,J.

  DOI：——

  日期：——