5-ethoxycarbonyl-3-methylcytosine | 90091-17-1

• 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-ethoxycarbonyl-3-methylcytosine
• 英文别名: 5-Ethoxycarbonyl-3-methylcytosin；6-amino-1-methyl-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid ethyl ester；6-Amino-1-methyl-2-oxo-1,2-dihydro-pyrimidin-5-carbonsaeure-aethylester；Ethyl 4-imino-3-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-amino-1-methyl-2-oxopyrimidine-5-carboxylate
• CAS: 90091-17-1
• 化学式: C₈H₁₁N₃O₃
• 分子量: 197.194
• InChiKey: RWPVDYXWCGXMAV-UHFFFAOYSA-N

物化性质

• 熔点：
  230 °C
• 沸点：
  321.7±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-ethoxycarbonyl-3-methylcytosine 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46%的产率得到3-methyl-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
• 作为产物：
  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：

文献信息

• [EN] PROCESS FOR PREPARING 5-(FLUORO-4-IMINO-3-METHYL)-1-TOSYL-3,4 DIHYDROPYRIMIDINE -(1H)-ONE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-(FLUORO-4-IMINO-3-MÉTHYL)-1-TOSYL-3,4-DIHYDROPYRIMIDINE-(1H)-ONE
  申请人：ADAMA MAKHTESHIM LTD

  公开号：WO2021059160A1

  公开（公告）日：2021-04-01

  The present invention provides a process for preparing a compound having the formula (I): wherein R is alkyl or alkylaryl; each of X1, X2, X3, X4 and X5 is, independently, H, alkyl, alkenyl, alkynyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, amino, alkylamino, dialkylamino, alkoxycarbonyl, alkyl carbonyl, hydroxyalkyl, ester, acid, halogen, -SH, -OH, -NH2, -NO2, -CN or CF3; Y is O or S; and and Z is a halogen.

  本发明提供了一种制备具有以下化学式（I）的化合物的方法：其中R是烷基或烷基芳基；X1、X2、X3、X4和X5中的每一个独立地是H、烷基、烯基、炔基、烷氧基、卤代烷基、卤代烷氧基、烷基硫基、卤代烷基硫基、氨基、烷基氨基、二烷基氨基、烷氧羰基、烷基羰基、羟基烷基、酯、酸、卤素、-SH、-OH、-NH2、-NO2、-CN或CF3；Y是O或S；Z是卤素。
• 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。
• Reactions of Orthoesters with Ureas. II
  作者：Calvert W. Whitehead、John J. Traverso

  DOI：10.1021/ja01627a029

  日期：1955.11
• 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：——