2,3-dihydro-6,8-bis(4-methoxyphenyl)-1H-indolizinium chloride | 132923-50-3

• 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: 2,3-dihydro-6,8-bis(4-methoxyphenyl)-1H-indolizinium chloride
• 英文别名: Ficuseptine；6,8-bis(4-methoxyphenyl)-2,3-dihydro-1H-indolizin-4-ium;chloride
• CAS: 132923-50-3
• 化学式: C₂₂H₂₂NO₂*Cl
• 分子量: 367.875
• InChiKey: UFYHQEGVTISHGS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  22.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-amino-3,5-bis(4-methoxyphenyl)pyridine 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 亚硝酸特丁酯 、 二碘甲烷 、 氢气 、 碘 、 甲基磺酰氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 40.0h， 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

文献信息

• Synthesis of Trisubstituted Pyridines<i>via</i>Chemoselective Suzuki-Miyaura Coupling of 3,5- and 4,6-Dibromo-2-tosyloxypyridines
  作者：Cho-Hee Park、Yong-Ju Kwon、In-Young Oh、Won-Suk Kim

  DOI：10.1002/adsc.201600950

  日期：2017.1.4

  diarylpyridine derivatives obtained was accomplished for the synthesis of novel and biologically relevant trisubstituted pyridines. The formal synthesis of ficuseptine, a bioactive alkaloid, has also been achieved via the palladium‐catalyzed cross‐coupling reaction of 3,5‐dibromo‐2‐tosyloxypyridine in 5 steps from 3,5‐dibromo‐2‐hydroxypyridine with 50% overall yield.

  已经研究了对3,5-和4,6-二溴-2-甲苯磺酰氧吡啶的化学选择性Suzuki-Miyaura反应，用于制备三取代的吡啶。优化的条件使得可以轻松获得3,5-和4,6-二芳基-2-甲苯磺酰氧吡啶，产率为8％至99％。进一步的功能化，如钯催化的胺化反应和所获得的二芳基吡啶衍生物中甲苯磺酸酯基团的无铜Sonogashira反应，可用于合成新型的和生物学上相关的三取代的吡啶。通过3,5-二溴-2-甲苯磺酰氧基吡啶在3,5-二溴-2-羟基吡啶的5个步骤中钯催化的交叉偶联反应也已完成了具有生物活性的生物碱生物碱的正式合成。屈服。
• Syntheses of Ficuseptine, Juliprosine, and Juliprosopine by Biomimetic Intramolecular Chichibabin Pyridine Syntheses
  作者：Barry B. Snider、Bobbianna J. Neubert

  DOI：10.1021/ol050931l

  日期：2005.6.1

  Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95 degrees C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25 degrees C if 1-pyrroline (5) is used instead of 6. This reaction has been used for a one-step synthesis of ficuseptine (1) and the first syntheses of juliprosine (2) and juliprosopine (17t), which is now assigned as the trans stereoisomer.