1H-吡咯-2-羧胺 | 105533-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1H-吡咯-2-羧胺
• 中文别名: 2-甲脒-1H-吡咯
• 英文名称: 2-pyrrolecarboxamidine
• 英文别名: 1H-pyrrole-2-carboximidamide；1H-pyrrol-2-carboximidamide
• CAS: 105533-75-3
• 化学式: C₅H₇N₃
• 分子量: 109.131
• InChiKey: FSUPKDUNLKQBCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.7
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1H-吡咯-2-羧胺 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.1h， 生成 5-phenyl-2-<2-(1-propy-2-ynylpyrryl)>pyrimidine
  参考文献：
  名称：

  Intramolecular Diels-Alder reactions of pyrimidines and a computational study toward their structure and reactivity

  摘要：

  The syntheses of 2-[(prop-2-ynyloxy)carbonyl]pyrimidine (1), 5-[(prop-2-ynyloxy)carbonyl]pyrimidine (2), 5-phenyl-2-[2-(1-prop-2-ynylpyrryl)]pyrimidine (8),5-phenyl-2-[2-(1-prop-2-ynylpyrrolidinyl)]pyrimidine (9) and 2-[2-(prop-2-ynyloxy)phenyl]-4,6-R2-5-R1-pyrimidine (R1 = H, Cl, Ph; R2 = H, Me) (14a-d) are described. Upon heating, the compounds 1, 9, and 14 undergo an intramolecular Diels-Alder reaction and a subsequent retro Diels-Alder reaction to yield the annelated pyridines 15, 16, and 17, respectively. The compounds 2 and 8 did not react. The nonreactivity of the compounds 2 and 8 is ascribed to conjugation of the pyrimidine aromatic system with part of the dienophilic side chain, giving rise to conformations in which the diene and dienophile moieties cannot interact. For the compounds 1, 9, and 14 conjugation is absent, due to steric hindrance. To support this, semiempirical (MDNO-PM3) and molecular mechanics (MMX, CHEMX) calculations were performed. The HOMO-LUMO energy separation of the compounds did not consequently reflect the observed reactivity. However, the probability of the compounds to be in a reactive conformation appeared to correlate with the observed rate of reaction (9 > 14a > 1 >> 2, 8).

  DOI：

  10.1021/jo00037a011
• 作为产物：
  描述：

  吡咯-2-腈 生成 1H-吡咯-2-羧胺
  参考文献：
  名称：

  Brunfelsamidine: a novel convulsant from the medicinal plant

  摘要：

  DOI：

  10.1016/s0040-4039(00)98119-x

文献信息

• 一种2-吡咯基嘧啶衍生物的制备方法
  申请人：湖南华腾制药有限公司

  公开号：CN106810538A

  公开（公告）日：2017-06-09

  本发明公开了一种2‑吡咯基嘧啶衍生物6‑氯‑2‑吡咯基嘧啶‑4‑羧酸甲酯的制备方法，以草酸二乙酯为起始原料，经过缩合、关环、氯化、酯化得到目标产物，该化合物是重要的医药中间体。