5-cyanomethyl-1,3-dimethyluracil | 79309-19-6

• 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-cyanomethyl-1,3-dimethyluracil
• 英文别名: 2-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acetonitrile；2-(1,3-Dimethyl-2,4-dioxopyrimidin-5-yl)acetonitrile
• CAS: 79309-19-6
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: WFTOUMKZNYJQMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 生成 5-cyanomethyl-1,3-dimethyluracil
  参考文献：
  名称：

  ITAHARA, TOSHIO;IDE, NAOKO, MED., BIOCHEM. AND CHEM. ASPECTS FREE RADICALS: PROC. 4TH BIENN. GEN. MEE+

  摘要：

  DOI：

文献信息

• Free Radical Alkylation of 1,3-Dimethyluracils and Caffeine with Benzoyl Peroxide
  作者：Toshio Itahara、Naoko Ide

  DOI：10.1246/bcsj.65.2045

  日期：1992.8

  3-dimethyluracils, although a steric effect of the methyl group at 6-position complicated the reaction. On the other hand, a similar treatment of 1,3-dimethylthymine led to alkylation of the methyl group at 5-position. The reaction of caffeine gave 8-alkylcaffeines and alkyl acetates were used as favorable solvents with respect to synthesis of 8-alkylcaffeines.

  1,3-二甲基尿嘧啶和 1,3,6-三甲基尿嘧啶与过氧化苯甲酰在环己烷、乙酸乙酯和乙腈中反应得到相应的 5-烷基-1,3-二甲基尿嘧啶，尽管甲基在 6-位置使反应复杂化。另一方面，1,3-二甲基胸腺嘧啶的类似处理导致5-位甲基的烷基化。咖啡因反应得到 8-烷基咖啡因，乙酸烷基酯用作合成 8-烷基咖啡因的有利溶剂。
• Xanthate-based microwave-assisted C H radical functionalization of caffeine, 1,3-dimethyluracil, and imidazo[1,2-a]pyridines
  作者：Víctor M. Pérez、Daniela Fregoso-López、Luis D. Miranda

  DOI：10.1016/j.tetlet.2017.02.050

  日期：2017.3

  Xanthate-based radical chemistry was used for the regioselective direct alkylation of caffeine, uracil, and imidazo[1,2-a]pyridine systems, using dilauroyl peroxide as initiator and oxidant, under microwave irradiation. Under these conditions, several electrophilic radicals (located alpha to a carbonyl function such as esters, amides, ketones, malonates and cyano groups) were added to the title heterocyclic

  基于黄药的自由基化学用于微波辐射下咖啡因，尿嘧啶和咪唑并[1,2-a]吡啶体系的区域选择性直接烷基化，使用过氧化二月桂酰作为引发剂和氧化剂。在这些条件下，将几个亲电基团（位于羰基官能团的α位，例如酯，酰胺，酮，丙二酸酯和氰基）添加到标题杂环系统中。该方法允许通过芳族取代中的C H官能化由容易获得的起始材料进行sp 2 -sp 3 C C键的分子间区域选择性构建。
• Novel C–C bond formation at the 5-position of uracils. Facile synthesis of 5-methoxycarbonylmethyluridine and 5-carbamoylmethyluridine, minor component nucleosides derived from transfer ribonuclease
  作者：Kosaku Hirota、Morio Suematsu、Yoshitaka Kuwabara、Tetsuji Asao、Shigeo Senda

  DOI：10.1039/c39810000623

  日期：——

  5-Hydroxyuracil derivatives were treated with stable Wittig reagents to give the corresponding 5-alkyluracil derivatives such as 5-methoxycarbonylmethyl-uridine and 5-carbamoylmethyluridine.

  用稳定的Wittig试剂处理5-羟基尿嘧啶衍生物，得到相应的5-烷基尿嘧啶衍生物，例如5-甲氧基羰基甲基尿苷和5-氨基甲酰基甲基尿苷。
• Itahara, Toshio; Ide, Naoko, Chemistry Letters, 1989, p. 977 - 980
  作者：Itahara, Toshio、Ide, Naoko

  DOI：——

  日期：——
• ITAHARA, TOSHIO;IDE, NAOKO, MED., BIOCHEM. AND CHEM. ASPECTS FREE RADICALS: PROC. 4TH BIENN. GEN. MEE+
  作者：ITAHARA, TOSHIO、IDE, NAOKO

  DOI：——

  日期：——