Thiophene-2-carboxylic acid [2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-thioacetyl]-amide | 648407-87-8

• 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: Thiophene-2-carboxylic acid [2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-thioacetyl]-amide
• 英文别名: N-[2-cyano-2-(triphenyl-lambda5-phosphanylidene)ethanethioyl]thiophene-2-carboxamide；N-[2-cyano-2-(triphenyl-λ5-phosphanylidene)ethanethioyl]thiophene-2-carboxamide
• CAS: 648407-87-8
• 化学式: C₂₆H₁₉N₂OPS₂
• 分子量: 470.555
• InChiKey: COKFCUAZARTJGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Thiophene-2-carboxylic acid [2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-thioacetyl]-amide 在 sodium hydroxide 、 硫酸 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 生成 (4-Methylsulfanyl-6-piperidin-1-yl-2-thiophen-2-yl-pyrimidin-5-yl)-triphenyl-phosphonium; perchlorate
  参考文献：
  名称：

  Syntheses of Functionalized Pyrimidines from the Products of Addition of Triphenylphosphoranylideneacetonitrile to Acyl Isothiocyanates

  摘要：

  The products of addition of accessible phosphorus-containing ylide Ph3P-CHCN to acyl and alkoxycarbonyl isocyanates readily cyclize under the action of methanolic HCl. This reaction was used for preparing a broad range of new 5-phosphonium derivatives of di- and trifunctionalized pyrimidine bases. Among them, the corresponding tertiary phosphonium salts containing no labile hydrogen atoms are especially important. Under mild conditions, they undergo dephosphorylation in the presence of alkalis to give 4-mercapto, 4,6-dimercapto-, and 2,4,6-trimercaptopyrimidine derivatives which are difficult or impossible to prepare by traditional routes.

  DOI：

  10.1023/b:rugc.0000045875.40116.eb
• 作为产物：
  描述：

  thiophene-2-carbonyl isothiocyanate 、 (三苯基膦)乙腈 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到Thiophene-2-carboxylic acid [2-cyano-2-(triphenyl-λ⁵-phosphanylidene)-thioacetyl]-amide
  参考文献：
  名称：

  Syntheses of Functionalized Pyrimidines from the Products of Addition of Triphenylphosphoranylideneacetonitrile to Acyl Isothiocyanates

  摘要：

  The products of addition of accessible phosphorus-containing ylide Ph3P-CHCN to acyl and alkoxycarbonyl isocyanates readily cyclize under the action of methanolic HCl. This reaction was used for preparing a broad range of new 5-phosphonium derivatives of di- and trifunctionalized pyrimidine bases. Among them, the corresponding tertiary phosphonium salts containing no labile hydrogen atoms are especially important. Under mild conditions, they undergo dephosphorylation in the presence of alkalis to give 4-mercapto, 4,6-dimercapto-, and 2,4,6-trimercaptopyrimidine derivatives which are difficult or impossible to prepare by traditional routes.

  DOI：

  10.1023/b:rugc.0000045875.40116.eb

文献信息

• Syntheses of Functionalized Pyrimidines from the Products of Addition of Triphenylphosphoranylideneacetonitrile to Acyl Isothiocyanates
  作者：L. V. Muzychka、O. B. Smolii、B. S. Drach

  DOI：10.1023/b:rugc.0000045875.40116.eb

  日期：2004.7

  The products of addition of accessible phosphorus-containing ylide Ph3P-CHCN to acyl and alkoxycarbonyl isocyanates readily cyclize under the action of methanolic HCl. This reaction was used for preparing a broad range of new 5-phosphonium derivatives of di- and trifunctionalized pyrimidine bases. Among them, the corresponding tertiary phosphonium salts containing no labile hydrogen atoms are especially important. Under mild conditions, they undergo dephosphorylation in the presence of alkalis to give 4-mercapto, 4,6-dimercapto-, and 2,4,6-trimercaptopyrimidine derivatives which are difficult or impossible to prepare by traditional routes.