ethyl 2-[(5,6-dicyano-3,3-dimethyl-3,4-dihydropyrazin-2-yl)amino]acetate | 1200592-26-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-[(5,6-dicyano-3,3-dimethyl-3,4-dihydropyrazin-2-yl)amino]acetate
• 英文别名: Ethyl 2-[(5,6-dicyano-3,3-dimethyl-1,4-dihydropyrazin-2-ylidene)amino]acetate；ethyl 2-[(5,6-dicyano-3,3-dimethyl-1,4-dihydropyrazin-2-ylidene)amino]acetate
• CAS: 1200592-26-2
• 化学式: C₁₂H₁₅N₅O₂
• 分子量: 261.283
• InChiKey: AIQBBJILQWGFQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  双乙烯酮 、 异氰基乙酸乙酯 、 二氨基马来腈 以 乙腈 为溶剂， 反应 24.0h， 以85%的产率得到ethyl 2-[(5,6-dicyano-3,3-dimethyl-3,4-dihydropyrazin-2-yl)amino]acetate
  参考文献：
  名称：

  Novel Syntheses of Tetrahydrobenzodiazepines and Dihydropyrazines via Isocyanide-Based Multicomponent Reactions of Diamines

  摘要：

  In this work, two novel isocyanide-based multicomponent reactions of 1,2-diamine compounds with diketene have been developed as efficient strategies for the synthesis of 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-2-carboxamides with regiochemical control and 1,6-dihydropyrazine-2,3-dicarbonitriles in good to excellent yields at ambient temperature.

  DOI：

  10.1021/cc900125a

文献信息

• Isocyanide-Based Three-Component Synthesis of Highly Substituted 1,6-Dihydro-6,6-dimethylpyrazine-2,3-dicarbonitrile, 3,4-Dihydrobenzo[g]quinoxalin-2-amine, and 3,4-Dihydro-3,3-dimethyl-quinoxalin-2-amine Derivatives
  作者：Ahmad Shaabani、Fatemeh Hajishaabanha、Hamid Mofakham、Mojtaba Mahyari、Bagher Lali

  DOI：10.1002/hlca.201100270

  日期：2012.2

  isocyanide‐based multicomponent reaction between alkyl or aryl isocyanides 1, 2,3‐diaminomaleonitrile (2), naphthalene‐2,3‐diamines (6) or benzene‐1,2‐diamine (9), and 3‐oxopentanedioic acid (3) or Meldrum's acid (4) or ketones 7 was developed for the ecologic synthesis, at room temperature under mild conditions, of 1,6‐dihydropyrazine‐2,3‐dicarbonitriles 5a–5f in H2O without using any catalyst, and of 3,4‐

  烷基或芳基之间的新颖的和有效的基于胩-多组分反应异腈1，2,3-二氨基（2），萘-2,3-二胺（6）或苯-1,2-二胺（9）和3-在室温和温和条件下，开发了氧合戊二酸（3）或Meldrum的酸（4）或酮7用于生态合成在H 2 O中不带H 2 O的1,6-二氢吡嗪-2,3-二碳腈5a - 5f。使用任何催化剂，以及3,4-二氢苯并[ g ]喹喔啉-2-胺和3,4-二氢-3,3-二甲基喹喔啉-2-胺衍生物在EtOH中催化量的对甲苯磺酸（TsOH）存在下，产率分别为8a – 8g和10a – 10e（方案1）。
• Novel Syntheses of Tetrahydrobenzodiazepines and Dihydropyrazines via Isocyanide-Based Multicomponent Reactions of Diamines
  作者：Ahmad Shaabani、Ali Maleki、Fatemeh Hajishaabanha、Hamid Mofakham、Mozhdeh Seyyedhamzeh、Mojtaba Mahyari、Seik Weng Ng

  DOI：10.1021/cc900125a

  日期：2010.1.11

  In this work, two novel isocyanide-based multicomponent reactions of 1,2-diamine compounds with diketene have been developed as efficient strategies for the synthesis of 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-2-carboxamides with regiochemical control and 1,6-dihydropyrazine-2,3-dicarbonitriles in good to excellent yields at ambient temperature.