2-amino-5-cyano-6-phenyl-4-thioxo-4H-pyran-3-ylphosphonic acid diethyl ester | 205595-43-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-amino-5-cyano-6-phenyl-4-thioxo-4H-pyran-3-ylphosphonic acid diethyl ester
• 英文别名: 6-Amino-5-diethoxyphosphoryl-2-phenyl-4-sulfanylidenepyran-3-carbonitrile
• CAS: 205595-43-3
• 化学式: C₁₆H₁₇N₂O₄PS
• 分子量: 364.362
• InChiKey: FKUILCSDAMVOND-UHFFFAOYSA-N

物化性质

• 沸点：
  442.7±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-amino-5-cyano-6-phenyl-4-thioxo-4H-pyran-3-ylphosphonic acid diethyl ester 在 ammonium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 2-amino-5-cyano-6-phenyl-4-methylsulfanylpyridin-3-ylphosphonic acid diethyl ester
  参考文献：
  名称：

  Pyrylium Salts of g-Thiapyrones --- A Simple Step to Phosphono-phosphino Substituted Pyridines and Pyridinium Salts

  摘要：

  The phosphono-phoshino substituted gamma-thiapyrones (1/2) are converted to pyrylium salts (3/4) with trimethyloxonium tetrafluoroborate (5) under mild conditions. Reactions of the pyrylium salts (3/4) with ammonia and primary amines (10) lead to phosphono-phosphino pyridines (6/7) and pyridinium salts (8/9).

  DOI：

  10.3987/com-98-8105
• 作为产物：
  描述：

  苯甲酰乙腈 、 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以71%的产率得到2-amino-5-cyano-6-phenyl-4-thioxo-4H-pyran-3-ylphosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis and Chemical Reactions of New Phosphono-phosphino Substituted g-Thiapyrones

  摘要：

  1,3-Dithietane-2,4-diylidenebis(cyanomethylphosphonates) and -phenylphosphinates (1/2) react with various substituted acetonitriles (3) to give phosphono-phosphino substituted gamma-thiapyrones (4/5). The constitution of one reaction product is confirmed by an X-ray crystal structure analysis (4.2 c). The gamma-thiapyrones are converted to boc-protected gamma-thiapyrones (6/7) and to gamma-pyrones (8/9) via oxidation.

  DOI：

  10.3987/com-97-s(n)9

文献信息

• Peptide Coupling Reactions with Phosphono-Phosphino Substituted γ-Thiapyrones — First Step to Unusual Peptides
  作者：Richard Neidlein、Dirk Uwe Hahn

  DOI：10.3987/com-98-s(h)108

  日期：——
• Synthesis and Chemical Reactions of New Phosphono-phosphino Substituted g-Thiapyrones
  作者：Richard Neidlein、Dirk Uwe Hahn、Walter Kramer、Claus Krieger

  DOI：10.3987/com-97-s(n)9

  日期：——

  1,3-Dithietane-2,4-diylidenebis(cyanomethylphosphonates) and -phenylphosphinates (1/2) react with various substituted acetonitriles (3) to give phosphono-phosphino substituted gamma-thiapyrones (4/5). The constitution of one reaction product is confirmed by an X-ray crystal structure analysis (4.2 c). The gamma-thiapyrones are converted to boc-protected gamma-thiapyrones (6/7) and to gamma-pyrones (8/9) via oxidation.
• Pyrylium Salts of g-Thiapyrones --- A Simple Step to Phosphono-phosphino Substituted Pyridines and Pyridinium Salts
  作者：Richard Neidlein、Dirk Uwe Hahn

  DOI：10.3987/com-98-8105

  日期：——

  The phosphono-phoshino substituted gamma-thiapyrones (1/2) are converted to pyrylium salts (3/4) with trimethyloxonium tetrafluoroborate (5) under mild conditions. Reactions of the pyrylium salts (3/4) with ammonia and primary amines (10) lead to phosphono-phosphino pyridines (6/7) and pyridinium salts (8/9).