[(E)-2-(6-Amino-purin-9-yl)-vinyl]-phosphonic acid diethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: [(E)-2-(6-Amino-purin-9-yl)-vinyl]-phosphonic acid diethyl ester
• 英文别名: 9-(2-diethoxyphosphorylethenyl)purin-6-amine
• 化学式: C₁₁H₁₆N₅O₃P
• 分子量: 297.253
• InChiKey: OINJDTAKENWHHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(E)-2-(6-Amino-purin-9-yl)-vinyl]-phosphonic acid diethyl ester 在 18-冠醚-6 、 三甲基溴硅烷 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.0h， 生成 (R,S)-9-<1-(2-hydroxyethylthio)-2-phosphonylethyl> adenine
  参考文献：
  名称：

  Synthesis of the Nucleotide Analogue: (R,S)-9-[1-(2-Hydroxyethylthio)-2-phosphonylethyl] Adenine

  摘要：

  The acyclic nucleotide analogue (R,S)-9-[1-(2-hydroxyethylthio)-2-phosphonylethyl] adenine [HETPEA, 4] was prepared by coupling the adenine potassium salt with diethyl ethynylphosphonate followed by condensation of the product with 2-mercaptoethanol.

  DOI：

  10.1080/15257779408013280
• 作为产物：
  描述：

  diethyl ethynylphosphonate 、 腺嘌呤 在 potassium carbonate 作用下， 生成 [(E)-2-(6-Amino-purin-9-yl)-vinyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of Acycloalkenyl Derivatives of Pyrimidines and Purines

  摘要：

  Conjugate addition of an anionic nucleophile (nucleobase) to an active triple bond (alpha, beta unsaturated carboxylate or phosphonate) was used for preparing alpha-ethenyl carboxylate or phosphonate derivatives of purines and pyrimidines.

  DOI：

  10.1080/15257779508012380

文献信息

• Synthesis of the Nucleotide Analogue: (R,S)-9-[1-(2-Hydroxyethylthio)-2-phosphonylethyl] Adenine
  作者：H. B. Lazrek、H. Khaider、A. Rochdi、J. L. Barascut、J. L. Imbach

  DOI：10.1080/15257779408013280

  日期：1994.3

  The acyclic nucleotide analogue (R,S)-9-[1-(2-hydroxyethylthio)-2-phosphonylethyl] adenine [HETPEA, 4] was prepared by coupling the adenine potassium salt with diethyl ethynylphosphonate followed by condensation of the product with 2-mercaptoethanol.
• Synthesis of Acycloalkenyl Derivatives of Pyrimidines and Purines
  作者：H. B. Lazrek、N. Redwane、A. Rochdi、J. L. Barascut、J. -L. Imbach、E. De Clercq

  DOI：10.1080/15257779508012380

  日期：1995.5.1

  Conjugate addition of an anionic nucleophile (nucleobase) to an active triple bond (alpha, beta unsaturated carboxylate or phosphonate) was used for preparing alpha-ethenyl carboxylate or phosphonate derivatives of purines and pyrimidines.