3-[3,5-bis(4-methoxyphenyl)pyridin-2-yl]-2-propyn-1-ol | 468066-76-4

• 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: 3-[3,5-bis(4-methoxyphenyl)pyridin-2-yl]-2-propyn-1-ol
• 英文别名: 3-[3,5-Bis(4-methoxyphenyl)pyridin-2-yl]prop-2-yn-1-ol
• CAS: 468066-76-4
• 化学式: C₂₂H₁₉NO₃
• 分子量: 345.398
• InChiKey: JOLCCFFIAIEVER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[3,5-bis(4-methoxyphenyl)pyridin-2-yl]-2-propyn-1-ol 在 palladium on activated charcoal 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3-dihydro-6,8-bis(4-methoxyphenyl)-1H-indolizinium chloride
  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-amino-3,5-bis(4-methoxyphenyl)pyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 亚硝酸特丁酯 、 二碘甲烷 、 碘 、 三乙胺 作用下， 反应 38.0h， 生成 3-[3,5-bis(4-methoxyphenyl)pyridin-2-yl]-2-propyn-1-ol
  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.