2-amino-3,5-bis(4-methoxyphenyl)pyridine | 468066-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-3,5-bis(4-methoxyphenyl)pyridine
• 英文别名: 3,5-Bis(4-methoxyphenyl)pyridin-2-amine
• CAS: 468066-71-9
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: XMDBFDVKBAGSGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-3,5-bis(4-methoxyphenyl)pyridine 在 亚硝酸特丁酯 、 potassium carbonate 、 copper(II) oxide 作用下， 以 乙醇 为溶剂， 反应 38.0h， 以50%的产率得到3,5-bis(4-methoxyphenyl)-1H-pyridin-2-one
  参考文献：
  名称：

  Total Synthesis of the Indolizidinium Alkaloid Ficuseptine

  摘要：

  The first total synthesis of ficuseptine [4,6-bis(4-methoxyphenyl)-1,2,3-trihydroindolizidinium chloride] (1), an alkaloid from Ficus septica, is described. The crucial steps in this five-step synthesis are a palladium-catalyzed bis(arylation) of a dibromopyridine under Suzuki conditions and a palladium-catalyzed alkynylation of an iodopyridine under Sonogashira conditions, as well as a novel Sandmeyer-type iodination of a 2-aminopyridine derivative. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200207)2002:14<2288::aid-ejoc2288>3.0.co;2-g
• 作为产物：
  描述：

  2-氨基-3,5-二溴吡啶 、 4-甲氧基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 65.0h， 以71%的产率得到2-amino-3,5-bis(4-methoxyphenyl)pyridine
  参考文献：
  名称：

  Total Synthesis of the Indolizidinium Alkaloid Ficuseptine

  摘要：

  The first total synthesis of ficuseptine [4,6-bis(4-methoxyphenyl)-1,2,3-trihydroindolizidinium chloride] (1), an alkaloid from Ficus septica, is described. The crucial steps in this five-step synthesis are a palladium-catalyzed bis(arylation) of a dibromopyridine under Suzuki conditions and a palladium-catalyzed alkynylation of an iodopyridine under Sonogashira conditions, as well as a novel Sandmeyer-type iodination of a 2-aminopyridine derivative. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200207)2002:14<2288::aid-ejoc2288>3.0.co;2-g

文献信息

• Total Synthesis of the Indolizidinium Alkaloid Ficuseptine
  作者：Franz Bracher、Jochen Daab

  DOI：10.1002/1099-0690(200207)2002:14<2288::aid-ejoc2288>3.0.co;2-g

  日期：2002.7

  The first total synthesis of ficuseptine [4,6-bis(4-methoxyphenyl)-1,2,3-trihydroindolizidinium chloride] (1), an alkaloid from Ficus septica, is described. The crucial steps in this five-step synthesis are a palladium-catalyzed bis(arylation) of a dibromopyridine under Suzuki conditions and a palladium-catalyzed alkynylation of an iodopyridine under Sonogashira conditions, as well as a novel Sandmeyer-type iodination of a 2-aminopyridine derivative. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.