ethyl (E)-2-cyano-3-(N'-methylureido)-2-propenoate | 5327-29-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 英文名称: ethyl (E)-2-cyano-3-(N'-methylureido)-2-propenoate
• 英文别名: 2-cyano-3-(N'-methyl-ureido)-acrylic acid ethyl ester；2-Cyan-3-(N'-methyl-ureido)-acrylsaeure-aethylester；ethyl (E)-2-cyano-3-(methylcarbamoylamino)prop-2-enoate
• CAS: 5327-29-7
• 化学式: C₈H₁₁N₃O₃
• 分子量: 197.194
• InChiKey: HJQUOJIOGWDIDS-AATRIKPKSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  302.7±42.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-cyano-3-(N'-methylureido)-2-propenoate 在 乙醇 、 sodium ethanolate 作用下， 生成 5-ethoxycarbonyl-3-methylcytosine
  参考文献：
  名称：

  Brown, Journal of Applied Chemistry, 1955, vol. 5, p. 358,362

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-cyano-3-(dimethylamino)acrylate 、 N-甲基脲 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以50%的产率得到ethyl (E)-2-cyano-3-(N'-methylureido)-2-propenoate
  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

• Cyclization Dichotomy of Esters of 3-Ureido-2-cyano-2-propenoic and 3-Ureido-2-acyl-2-propenoic Acids
  作者：Miroslav Ledvina、Jiří Farkaš

  DOI：10.1135/cccc19941841

  日期：——

  The preparation of E and Z isomers of 3-ureido-2-cyano-2-propenoates Ia - Id and their base-catalyzed isomerization and cyclization to 5-carboxycytosine derivatives IIa - IIf and 5-cyanouracil derivatives IIIa and IIIb is described. Also described is the preparation of 3-ureido-2-acyl-2-propenoates Va - Vd and their base-catalyzed cyclization to 5-carboxy-2(1H)-pyrimidone derivatives VIa - VIc and 5-acyluracils VIIa - VIIc.

  描述了3-脲基-2-氰基-2-丙烯酸酯的Ia - Id的E和Z异构体的制备，以及它们的碱催化异构化和环化到5-羧基胞嘧啶衍生物IIa - IIf和5-氰基尿嘧啶衍生物IIIa和IIIb。还描述了3-脲基-2-酰基-2-丙烯酸酯Va - Vd的制备及其碱催化环化到5-羧基-2(1H)-嘧啶酮衍生物VIa - VIc和5-酰基尿嘧啶VIIa - VIIc。
• Process for production of pyrimidines
  申请人：LILLY CO ELI

  公开号：US02774760A1

  公开（公告）日：1956-12-18
• Deshmukh M., Mittelbach M., Junek H., Monatsh. Chem, 126 (1995) N 1, S 91-97
  作者：Deshmukh M., Mittelbach M., Junek H.

  DOI：——

  日期：——
• Brown, Journal of Applied Chemistry, 1955, vol. 5, p. 358,362
  作者：Brown

  DOI：——

  日期：——
• 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.