3-acetyloxymethyl-5-fluorouracil | 73042-04-3

• 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: 3-acetyloxymethyl-5-fluorouracil
• 英文别名: (5-fluoro-2,4-dioxo-1H-pyrimidin-3-yl)methyl acetate
• CAS: 73042-04-3
• 化学式: C₇H₇FN₂O₄
• 分子量: 202.142
• InChiKey: DUAAVZPXVWYBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-ethyloxycarbonyl-3-acetyloxymethyl-5-fluorouracil 在 叔丁胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到3-acetyloxymethyl-5-fluorouracil
  参考文献：
  名称：

  Synthesis of 3‐alkylcarbonyloxymethyl derivatives of 5‐fluorouracil

  摘要：

  Abstract3‐Alkylcarbonyloxymethyl derivatives of 5‐fluorouracil have been synthesized starting with 1‐ethyloxy‐carbonyl‐5‐fluorouracil. Alkylation of the starting material with alkylcarbonyloxymethyl iodides, generated from the corresponding chlorides by the Finkelstein reaction, in the presence of 1,8‐bis(dimethyl‐amino)naphthalene followed by deprotection with 1,1‐dimethylethylamine gave good yields (50‐60%) of the target derivatives after column chromatography. A 90% yield of 3‐acetyloxymethyl‐5‐fluorouracil was obtained when the corresponding commercially available bromide was used, instead of the in situ generated iodide, and the product could be isolated from the crude reaction by crystallization. An alternate path of sequential alkylation of 5‐fluorouracil with alkylcarbonyloxymethyl chlorides in the presence of tertiary amines, exhibiting different reactivities towards the chlorides, gave an excellent yield of 1‐acetyloxymethyl‐3‐propionyloxymethyl‐5‐fluorouracil in the one instance it was attempted, but subsequent deprotection of the 1‐position with methylamine gave only a 24% yield of 3‐propionyloxymethyl‐5‐fluorouracil.

  DOI：

  10.1002/jhet.5570390509

文献信息

• JPH03112929A
  申请人：——

  公开号：JPH03112929A

  公开（公告）日：1991-05-14
• JPS54122281A
  申请人：——

  公开号：JPS54122281A

  公开（公告）日：1979-09-21
• Synthesis of 3‐alkylcarbonyloxymethyl derivatives of 5‐fluorouracil
  作者：William J. Roberts、Kenneth B. Sloan

  DOI：10.1002/jhet.5570390509

  日期：2002.9

  Abstract3‐Alkylcarbonyloxymethyl derivatives of 5‐fluorouracil have been synthesized starting with 1‐ethyloxy‐carbonyl‐5‐fluorouracil. Alkylation of the starting material with alkylcarbonyloxymethyl iodides, generated from the corresponding chlorides by the Finkelstein reaction, in the presence of 1,8‐bis(dimethyl‐amino)naphthalene followed by deprotection with 1,1‐dimethylethylamine gave good yields (50‐60%) of the target derivatives after column chromatography. A 90% yield of 3‐acetyloxymethyl‐5‐fluorouracil was obtained when the corresponding commercially available bromide was used, instead of the in situ generated iodide, and the product could be isolated from the crude reaction by crystallization. An alternate path of sequential alkylation of 5‐fluorouracil with alkylcarbonyloxymethyl chlorides in the presence of tertiary amines, exhibiting different reactivities towards the chlorides, gave an excellent yield of 1‐acetyloxymethyl‐3‐propionyloxymethyl‐5‐fluorouracil in the one instance it was attempted, but subsequent deprotection of the 1‐position with methylamine gave only a 24% yield of 3‐propionyloxymethyl‐5‐fluorouracil.