5-(chloromethyl)-1,3-dimethyluracil | 32079-06-4

• 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: 5-(chloromethyl)-1,3-dimethyluracil
• 英文别名: 1,3-dimethyl-5-chloromethyluracil；5-chloromethyl-1,3-dimethyluracil；5-chloromethyl-1,3-dimethyl-1H-pyrimidine-2,4-dione；1,3-Dimethyl-5-chlormethyluracil；5-Chlormethyl-1,3-dimethyluracil；5-(chloromethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione；5-(chloromethyl)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 32079-06-4
• 化学式: C₇H₉ClN₂O₂
• mdl: MFCD09025346
• 分子量: 188.614
• InChiKey: WFKQKJIPEIXIGO-UHFFFAOYSA-N

物化性质

• 沸点：
  259.9±42.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(chloromethyl)-1,3-dimethyluracil 在 silver perchlorate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Reduction of 5-uracilylmethylenepyridinium salts by thiols. A model of the reduction step of the thymidylate synthase reaction

  摘要：

  Reaction of 1-(5-uracilylmethylene)pyridinium salts with thiols leads to the formation of the corresponding thymine derivatives. This transformation of a uracil derivative to the corresponding thymine is explained on the basis of the formation of an exocyclicmethylene intermediate, analogous to that proposed in the thymidylate synthase reaction, followed by its reduction by additional thiol, presumably involving a radical mechanism.

  DOI：

  10.1016/s0040-4020(01)87105-2
• 作为产物：
  描述：

  聚合甲醛 、 1,3-二甲基脲嘧啶 在 HCl 作用下， 以 盐酸 为溶剂， 反应 2.0h， 以87%的产率得到5-(chloromethyl)-1,3-dimethyluracil
  参考文献：
  名称：

  Reduction of 5-uracilylmethylenepyridinium salts by thiols. A model of the reduction step of the thymidylate synthase reaction

  摘要：

  Reaction of 1-(5-uracilylmethylene)pyridinium salts with thiols leads to the formation of the corresponding thymine derivatives. This transformation of a uracil derivative to the corresponding thymine is explained on the basis of the formation of an exocyclicmethylene intermediate, analogous to that proposed in the thymidylate synthase reaction, followed by its reduction by additional thiol, presumably involving a radical mechanism.

  DOI：

  10.1016/s0040-4020(01)87105-2

文献信息

• Elimination reactions of .alpha.-substituted thymines derived from tautomeric heterocyclic thiols and selenols
  作者：James R. Bartels-Keith、J. Barry Mahoney、Anthony J. Puttick

  DOI：10.1021/jo00207a015

  日期：1985.4
• Wagner, Roman; Dvorak, Dalimil; Holy, Antonin, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S118 - S119
  作者：Wagner, Roman、Dvorak, Dalimil、Holy, Antonin

  DOI：——

  日期：——
• YAGIHARA, MORIO;IKEGAWA, AKIHIKO
  作者：YAGIHARA, MORIO、IKEGAWA, AKIHIKO

  DOI：——

  日期：——
• US4690885A
  申请人：——

  公开号：US4690885A

  公开（公告）日：1987-09-01
• Reduction of 5-uracilylmethylenepyridinium salts by thiols. A model of the reduction step of the thymidylate synthase reaction
  作者：Erwin Vega、Geertruida A. Rood、Eduard R. de Waard、Upendra K. Pandit

  DOI：10.1016/s0040-4020(01)87105-2

  日期：1991.1

  Reaction of 1-(5-uracilylmethylene)pyridinium salts with thiols leads to the formation of the corresponding thymine derivatives. This transformation of a uracil derivative to the corresponding thymine is explained on the basis of the formation of an exocyclicmethylene intermediate, analogous to that proposed in the thymidylate synthase reaction, followed by its reduction by additional thiol, presumably involving a radical mechanism.