3-ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester | 168428-18-0

• 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-ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: 3-Aethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-carbonsaeure-aethylester；Ethyl 3-ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 3-ethyl-2,4-dioxo-1H-pyrimidine-5-carboxylate
• CAS: 168428-18-0
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: NOCBPBUSWKOOBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 生成 3-ethyl-1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  The Synthesis of 5-Carbethoxyuracils

  摘要：

  DOI：

  10.1021/ja01137a008
• 作为产物：
  描述：

  1-ethyl-6-amino-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester 在 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以50%的产率得到3-ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Syntheses with nitriles, XCV: Deamination of cytosine derivatives

  摘要：

  Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cyano-, and 5-alkoxycarbonyl-2-oxopyrimidine derivatives 3, 6, and 7. Reaction of 3 with isopentylnitrite gave a mixture of the deaminated and oxidized product 4 and the oxo derivative 5, which was acetalized during the separation step. Similar reaction with the alkoxycarbonyl derivatives 7 led to the formation of 1-alkyl-5-alkoxycarbonyl-pyrimidine-2,6-diones 8a-d.

  DOI：

  10.1007/bf00811761

文献信息

• TETRAZOLE DERIVATIVES AS TRPA1 INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20220002270A1

  公开（公告）日：2022-01-06

  The present disclosure provides certain tetrazole derivatives that are inhibitors of transient receptor potential ankyrin 1 (TRPA1), and are therefore useful for the treatment of diseases treatable by inhibition of TRPA1. Also provided are pharmaceutical compositions containing the same, and processes for preparing said compounds.

  本公开提供了一些噻唑醇衍生物，它们是暂时性受体电位蛋白1（TRPA1）的抑制剂，因此可用于治疗通过抑制TRPA1可治疗的疾病。还提供了含有这些衍生物的药物组合物，以及制备这些化合物的方法。
• The Synthesis of 5-Carbethoxyuracils
  作者：Calvert W. Whitehead

  DOI：10.1021/ja01137a008

  日期：1952.9
• Syntheses with nitriles, XCV: Deamination of cytosine derivatives
  作者：M. Deshmukh、M. Mittelbach、H. Junek

  DOI：10.1007/bf00811761

  日期：1995.1

  Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cyano-, and 5-alkoxycarbonyl-2-oxopyrimidine derivatives 3, 6, and 7. Reaction of 3 with isopentylnitrite gave a mixture of the deaminated and oxidized product 4 and the oxo derivative 5, which was acetalized during the separation step. Similar reaction with the alkoxycarbonyl derivatives 7 led to the formation of 1-alkyl-5-alkoxycarbonyl-pyrimidine-2,6-diones 8a-d.