p-Nitrophenyl 4-Chloro-2-butynoate | 93524-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: p-Nitrophenyl 4-Chloro-2-butynoate
• 英文别名: p-nitrophenyl chlorotetrolate；4-Nitrophenyl 4-chlorobut-2-ynoate；(4-nitrophenyl) 4-chlorobut-2-ynoate
• CAS: 93524-35-7
• 化学式: C₁₀H₆ClNO₄
• 分子量: 239.615
• InChiKey: OMGGEQGYSPEISB-UHFFFAOYSA-N

物化性质

• 沸点：
  383.2±42.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-Nitrophenyl 4-Chloro-2-butynoate 、 胞苷 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以50%的产率得到1-β-D-Ribofuranosyl-2,6-dihydro-4-(chloromethyl)-2,6-dioxopyrimido<1,2-c>pyrimidine
  参考文献：
  名称：

  Reaction of nucleic acid bases with .alpha.-acetylenic esters. 5. Synthesis and properties of adenosine and cytidine derivatives

  摘要：

  Alpha-Acetylenic esters are able to react under mild experimental conditions with the base moiety of adenosine and cytidine, while guanosine is unreactive. A double reaction of the triple bond and the ester group of the reagent with the NH2 group and the adjacent ring nitrogen of the base yields derivatives in which an additional pyrimidone ring is fused to the original base. These derivatives can exist in two isomeric forms. In alkaline solution, or by prolonged heating in water, the medium pyrimidine ring of adenosine derivatives opens by loss of carbon 5. If the derivatization is performed with chlorotetrolic (4-chloro-2-butynoic) acid esters, the modified nucleobases contain a chloromethyl side chain. Tests of the alkylating abilities of the latter in the two isomeric adenosine derivatives show that the chlorine can be easily substituted by a thiol in the presence of alkali; a partial Dimroth rearrangement of one of the reaction products is observed. The reaction with amines is accompanied by ring opening. Nucleic acids containing these alkylating base derivatives can be cross-linked to other macromolecules such as solid supports or contact proteins.

  DOI：

  10.1021/jo00031a045
• 作为产物：
  描述：

  对硝基苯酚 、 氯甲基丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到p-Nitrophenyl 4-Chloro-2-butynoate
  参考文献：
  名称：

  Reaction of nucleic acid bases with .alpha.-acetylenic esters. 5. Synthesis and properties of adenosine and cytidine derivatives

  摘要：

  Alpha-Acetylenic esters are able to react under mild experimental conditions with the base moiety of adenosine and cytidine, while guanosine is unreactive. A double reaction of the triple bond and the ester group of the reagent with the NH2 group and the adjacent ring nitrogen of the base yields derivatives in which an additional pyrimidone ring is fused to the original base. These derivatives can exist in two isomeric forms. In alkaline solution, or by prolonged heating in water, the medium pyrimidine ring of adenosine derivatives opens by loss of carbon 5. If the derivatization is performed with chlorotetrolic (4-chloro-2-butynoic) acid esters, the modified nucleobases contain a chloromethyl side chain. Tests of the alkylating abilities of the latter in the two isomeric adenosine derivatives show that the chlorine can be easily substituted by a thiol in the presence of alkali; a partial Dimroth rearrangement of one of the reaction products is observed. The reaction with amines is accompanied by ring opening. Nucleic acids containing these alkylating base derivatives can be cross-linked to other macromolecules such as solid supports or contact proteins.

  DOI：

  10.1021/jo00031a045

文献信息

• Reaction of nucleobases with α-acetylenic esters, potentially useful for chemical modification of nucleic acids
  作者：M. Olomucki、J.Y. Le Gall、S. Colinart、F. Durant、B. Norberg、G. Evrard

  DOI：10.1016/s0040-4039(01)91050-0

  日期：1984.1
• Reaction of nucleic acid bases with .alpha.-acetylenic esters. 5. Synthesis and properties of adenosine and cytidine derivatives
  作者：Pierre Roques、Jean Yves Le Gall、Liliane Lacombe、Martin Olomucki

  DOI：10.1021/jo00031a045

  日期：1992.2

  Alpha-Acetylenic esters are able to react under mild experimental conditions with the base moiety of adenosine and cytidine, while guanosine is unreactive. A double reaction of the triple bond and the ester group of the reagent with the NH2 group and the adjacent ring nitrogen of the base yields derivatives in which an additional pyrimidone ring is fused to the original base. These derivatives can exist in two isomeric forms. In alkaline solution, or by prolonged heating in water, the medium pyrimidine ring of adenosine derivatives opens by loss of carbon 5. If the derivatization is performed with chlorotetrolic (4-chloro-2-butynoic) acid esters, the modified nucleobases contain a chloromethyl side chain. Tests of the alkylating abilities of the latter in the two isomeric adenosine derivatives show that the chlorine can be easily substituted by a thiol in the presence of alkali; a partial Dimroth rearrangement of one of the reaction products is observed. The reaction with amines is accompanied by ring opening. Nucleic acids containing these alkylating base derivatives can be cross-linked to other macromolecules such as solid supports or contact proteins.