1-ethyl-5-(4,5,6-trichloropyrimidin-2-yl)-1-H-pyrrol-2-amine | 937180-24-0

• 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: 1-ethyl-5-(4,5,6-trichloropyrimidin-2-yl)-1-H-pyrrol-2-amine
• 英文别名: 1-Ethyl-5-(2,5,6-trichloropyrimidin-4-yl)pyrrol-2-amine；1-ethyl-5-(2,5,6-trichloropyrimidin-4-yl)pyrrol-2-amine
• CAS: 937180-24-0
• 化学式: C₁₀H₉Cl₃N₄
• 分子量: 291.567
• InChiKey: SJFMSNQSZYUFFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethyl-5-(4,5,6-trichloropyrimidin-2-yl)-1-H-pyrrol-2-amine 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 7-Ethyl-6-(2,5,6-trichloropyrimidin-4-yl)-2,4-bis(trifluoromethyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Mechanism of the inverse-electron demand Diels–Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid

  摘要：

  In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.012
• 作为产物：
  描述：

  2,4,5,6-四氯嘧啶 、 1-ethyl-2-ammoniopyrrole tetraphenylborate 以 四氢呋喃 、 三乙胺 为溶剂， 反应 3.75h， 以32%的产率得到1-ethyl-5-(4,5,6-trichloropyrimidin-2-yl)-1-H-pyrrol-2-amine
  参考文献：
  名称：

  The first example of tautomerism in 2-aminopyrroles: effect of structure and solvent

  摘要：

  Amino/imino tautomerism is observed in secondary 2-aminopyrroles when an electron-withdrawing group is on the amino group. The amino tautomer was favored in solvents that were hydrogen bond acceptors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.100

文献信息

• The first example of tautomerism in 2-aminopyrroles: effect of structure and solvent
  作者：Michael De Rosa、David Arnold、Bernie O’Hare

  DOI：10.1016/j.tetlet.2008.10.100

  日期：2009.1

  Amino/imino tautomerism is observed in secondary 2-aminopyrroles when an electron-withdrawing group is on the amino group. The amino tautomer was favored in solvents that were hydrogen bond acceptors. (C) 2008 Elsevier Ltd. All rights reserved.
• Mechanism of the inverse-electron demand Diels–Alder reaction of 2-aminopyrroles with 1,3,5-triazines: detection of an intermediate and effect of added base and acid
  作者：Michael De Rosa、David Arnold

  DOI：10.1016/j.tetlet.2007.03.012

  日期：2007.4

  In base, a 2-aminopyrrole reacted with a 1,3,5-triazine to give a zwitterion (Meisenheimer complex). Acid promoted its conversion to the pyrrolo[2,3-d]pyrimidine. A cascade mechanism with reversible steps is proposed to explain why both a base and an acid are needed for the cycloaddition to occur. (c) 2007 Elsevier Ltd. All rights reserved.