1-diazo-3-<(2-benzoxazolyl)thio>-2-propanone | 91226-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 1-diazo-3-<(2-benzoxazolyl)thio>-2-propanone
• 英文别名: 1-diazo-3-(2-benzoxazolylmercapto)propanone；3-[(1,3-Benzoxazol-2-yl)sulfanyl]-1-diazonioprop-1-en-2-olate；1-(1,3-benzoxazol-2-ylsulfanyl)-3-diazopropan-2-one
• CAS: 91226-70-9
• 化学式: C₁₀H₇N₃O₂S
• 分子量: 233.25
• InChiKey: HVNGPNQUDQEGIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-diazo-3-<(2-benzoxazolyl)thio>-2-propanone 在 高氯酸 作用下， 以 乙腈 为溶剂， 以85%的产率得到5-oxo-5,6-dihydro-4H-1,3-thiazino<2,3-b>benzoxazolium perchlorate
  参考文献：
  名称：

  杂环的重氮羰基衍生物。5.2-杂芳基巯基烷基-重氮酮的分子内环化。缩合的1,3-噻嗪-5-酮的合成

  摘要：

  DOI：

  10.1007/bf00514302
• 作为产物：
  描述：

  1-bromo-3-diazopropan-2-one 、 2-巯基苯并恶唑 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以60%的产率得到1-diazo-3-<(2-benzoxazolyl)thio>-2-propanone
  参考文献：
  名称：

  Diazo carbonyl derivatives of heterocycles. 4. Diazoacetyl derivatives of mercaptobenzazoles and mercaptoquinolines

  摘要：

  DOI：

  10.1007/bf00514301

文献信息

• Cycloaddition reactions of pyridinium and related azomethine ylides
  作者：Albert Padwa、David J. Austin、Laura Precedo、Lin Zhi

  DOI：10.1021/jo00057a029

  日期：1993.2

  The Rh(H)-catalyzed reaction of alpha-diazoacetophenone in the presence of 2-(methylthio)pyridine and dimethyl acetylenedicarboxylate gave 3-benzoyl-1,2-dicarbomethoxy-3,5-dihydro-5-(methylthio)-indolizine. The formation of the cycloadduct proceeds via a pyridinium ylide formed by attack of the nitrogen lone pair on the electrophilic keto carbenoid. A related cyclization occurred using 1-diazo-3-[(2-pyridyl)thio]-2-propanone. The Rh(II)-catalyzed reaction of 1-(3'-diazoacetonyl)-2-pyridone with DMAD was also found to give cycloadducts derived from an azomethine ylide. The initial reaction involves generation of the expected carbonyl ylide dipole by intramolecular cyclization of the keto carbenoid onto the oxygen atom of the amide group. A subsequent proton exchange generates the thermodynamically more stable azomethine ylide which is trapped by DMAD. Azomethine ylide cycloadducts derived from keto carbenoid cyclization onto a thiobenzoxazole are also formed. When 1-diazo-3-[(2-benzoxazolyl)thio]-2-propanone was used, the initially formed cycloadduct underwent a subsequent 1,3-sigmatropic thio shift. An analogous cyclization occurred using 2-(4-diazo-3-oxobutyl)benzoxazole. In addition to undergoing dipolar cycloaddition, the highly stabilized dipole formed from this benzoxazole loses a proton to produce a cyclic ketene N,O-acetal. This compound reacts further with DMAD to eventually produce a novel phenolic lactam whose structure was established by an X-ray crystal structure analysis.
• Synthesis, solvolysis kinetics, and antileukemic activity of 1-diazo-3-(2′-thiohetaryl) alkan-2-ones
  作者：V. G. Kartsev、T. S. Pokidova、T. G. Denisova、L. S. Vasil'eva

  DOI：10.1007/bf00766680

  日期：1985.7
• Padwa Albert, Austin David J., Precedo Laura, Zhi Lin, J. Org. Chem., 58 (1993) N 5, S 1144-1150
  作者：Padwa Albert, Austin David J., Precedo Laura, Zhi Lin

  DOI：——

  日期：——
• KARTSEV, V. G.;POKIDOVA, T. S.;DOVGILEVICH, A. V., XIMIYA GETEROTSIKL. SOEDIN., 1984, N 5, 635-639
  作者：KARTSEV, V. G.、POKIDOVA, T. S.、DOVGILEVICH, A. V.

  DOI：——

  日期：——
• KARTSEV, V. G.;POKIDOVA, T. S.;DOVGILEVICH, A. V., XIMIYA GETEROTSIKL. SOEDIN., 1984, N 5, 632-634
  作者：KARTSEV, V. G.、POKIDOVA, T. S.、DOVGILEVICH, A. V.

  DOI：——

  日期：——