2-ethyl pyrimidinylhydrazocarboxylate

• 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: 2-ethyl pyrimidinylhydrazocarboxylate
• 英文别名: ethyl N-(pyrimidin-2-ylamino)carbamate
• 化学式: C₇H₁₀N₄O₂
• 分子量: 182.182
• InChiKey: APWQDIJJHLGGHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethyl pyrimidinylhydrazocarboxylate 在 lead(IV) acetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到2-ethyl pyrimidinyldiazenecarboxylate
  参考文献：
  名称：

  Toward Enediyne Mimics:  Methanolysis of Azoesters and a Bisazoester

  摘要：

  Enediyne anticancer antibiotics have attracted tremendous interest in the past decade. The inherent difficulty in synthesizing these structurally complex natural products with the strained enediyne moiety has motivated a search for simpler molecules that mimic enediyne chemistry. The ultimate objective is to identify molecules that produce 1,4-benzenoid diradicals, which are known to induce DNA cleavage in the natural products. Toward this goal, several aromatic azoesters have been synthesized, and EPR reveals the presence of radical intermediates in their methanolysis. A 1,4-bisazoester has also been synthesized, and its methanolysis products have been studied by reversed-phase HPLC. The formation of 1,2-dicyanobenzene from the 1,4-bisazoester is consistent with the existence of a 1,4-diradical intermediate.

  DOI：

  10.1021/jo990750v
• 作为产物：
  描述：

  2-肼基嘧啶 、 氯甲酸乙酯 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以82%的产率得到2-ethyl pyrimidinylhydrazocarboxylate
  参考文献：
  名称：

  Toward Enediyne Mimics:  Methanolysis of Azoesters and a Bisazoester

  摘要：

  Enediyne anticancer antibiotics have attracted tremendous interest in the past decade. The inherent difficulty in synthesizing these structurally complex natural products with the strained enediyne moiety has motivated a search for simpler molecules that mimic enediyne chemistry. The ultimate objective is to identify molecules that produce 1,4-benzenoid diradicals, which are known to induce DNA cleavage in the natural products. Toward this goal, several aromatic azoesters have been synthesized, and EPR reveals the presence of radical intermediates in their methanolysis. A 1,4-bisazoester has also been synthesized, and its methanolysis products have been studied by reversed-phase HPLC. The formation of 1,2-dicyanobenzene from the 1,4-bisazoester is consistent with the existence of a 1,4-diradical intermediate.

  DOI：

  10.1021/jo990750v

文献信息

• Toward Enediyne Mimics:  Methanolysis of Azoesters and a Bisazoester
  作者：Veeraraghavan Srinivasan、David J. Jebaratnam、David E. Budil

  DOI：10.1021/jo990750v

  日期：1999.7.1

  Enediyne anticancer antibiotics have attracted tremendous interest in the past decade. The inherent difficulty in synthesizing these structurally complex natural products with the strained enediyne moiety has motivated a search for simpler molecules that mimic enediyne chemistry. The ultimate objective is to identify molecules that produce 1,4-benzenoid diradicals, which are known to induce DNA cleavage in the natural products. Toward this goal, several aromatic azoesters have been synthesized, and EPR reveals the presence of radical intermediates in their methanolysis. A 1,4-bisazoester has also been synthesized, and its methanolysis products have been studied by reversed-phase HPLC. The formation of 1,2-dicyanobenzene from the 1,4-bisazoester is consistent with the existence of a 1,4-diradical intermediate.