[(E)-2-(5-Hydroxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-vinyl]-phosphonic acid diethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: [(E)-2-(5-Hydroxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-vinyl]-phosphonic acid diethyl ester
• 英文别名: 1-[(E)-2-diethoxyphosphorylvinyl]-5-(hydroxymethyl)pyrimidine-2,4-dione；1-[(E)-2-diethoxyphosphorylethenyl]-5-(hydroxymethyl)pyrimidine-2,4-dione
• 化学式: C₁₁H₁₇N₂O₆P
• 分子量: 304.24
• InChiKey: VGYAWRHEKFFPGY-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(E)-2-(5-Hydroxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-vinyl]-phosphonic acid diethyl ester 在 三甲基溴硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到[(E)-2-[5-(hydroxymethyl)-2,4-dioxo-pyrimidin-1-yl]vinyl]phosphonic acid
  参考文献：
  名称：

  Synthesis of (Z) and (E) α-alkenyl phosphonic acid derivatives of purines and pyrimidines

  摘要：

  (Z) and (E)-2-(purin-9-yl/pyrimidin-1-yl)ethylen-1-ylphosphonic acid 10-18 were synthetized by Michael addition of heterocyclic base with the diethylethynylphosphonate and deprotection of the acyclic nucleoside phosphonate with bromotrimethylsilane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00107-0
• 作为产物：
  描述：

  5-羟甲基脲嘧啶 、 diethyl ethynylphosphonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51%的产率得到[(E)-2-(5-Hydroxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-vinyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of (Z) and (E) α-alkenyl phosphonic acid derivatives of purines and pyrimidines

  摘要：

  (Z) and (E)-2-(purin-9-yl/pyrimidin-1-yl)ethylen-1-ylphosphonic acid 10-18 were synthetized by Michael addition of heterocyclic base with the diethylethynylphosphonate and deprotection of the acyclic nucleoside phosphonate with bromotrimethylsilane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00107-0

文献信息

• Synthesis of (Z) and (E) α-alkenyl phosphonic acid derivatives of purines and pyrimidines
  作者：H.B. Lazrek、A. Rochdi、H. Khaider、J.-L. Barascut、J.-L. Imbach、J. Balzarini、M. Witvrouw、C. Pannecouque、E. De Clercq

  DOI：10.1016/s0040-4020(98)00107-0

  日期：1998.4

  (Z) and (E)-2-(purin-9-yl/pyrimidin-1-yl)ethylen-1-ylphosphonic acid 10-18 were synthetized by Michael addition of heterocyclic base with the diethylethynylphosphonate and deprotection of the acyclic nucleoside phosphonate with bromotrimethylsilane. (C) 1998 Elsevier Science Ltd. All rights reserved.