scalaridine A | 1421751-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: scalaridine A
• 英文别名: 3-[5-(5-hydroxy-1H-indol-3-yl)pyridin-3-yl]-1H-indol-5-ol
• CAS: 1421751-01-0
• 化学式: C₂₁H₁₅N₃O₂
• 分子量: 341.369
• InChiKey: LIZCHFXYCGUVKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.93
• 氢给体数：
  4.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3,5-二溴吡啶 在 potassium phosphate 、 copper(l) iodide 、 三溴化硼 、 N,N-二乙基乙二胺 、 sodium iodide 、 copper dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 scalaridine A
  参考文献：
  名称：

  铜催化的见解：铃木-宫浦的芳基/吲哚基硼酸酯交叉偶联中原位形成的纳米Cu 2 O

  摘要：

  已经研究了无配体铜催化3,5-二碘吡啶与芳基和吲哚硼酸酯的Suzuki-Miyaura偶联，收率良好。原位生成的纳米铜的2从氯化亚铜ø 2在反应条件下已经发现首次。通过5-碘嘧啶，碘吡啶，碘苯和二碘苯的芳基化进一步证明了反应的一般性，并产生了良好至中等的收率。此外，双吲哚生物碱Scalaridine A已成功地以60％的总收率合成。

  DOI：

  10.1021/acs.orglett.7b01669

文献信息

• Short syntheses of the indole alkaloids alocasin A, scalaridine A, and hyrtinadine A-B
  作者：Nurul H. Ansari、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2016.05.057

  日期：2016.7

  Expedient syntheses of the indole alkaloids alocasin A, scalaridine A, and hyrtinadine A-B are presented. All four natural products contain one or two 5-hydroxyindolyl units. Three palladium catalyzed reactions, an alkyne hydrostannylation, a Kosugi-Migita-Stille cross coupling and a reductive N-heterocyclization are the key steps in the syntheses.

  提出了吲哚生物碱alocasin A，scalaridine A和hyrtinadine AB的简便合成方法。所有四种天然产物均包含一个或两个5-羟基吲哚基单元。合成过程中的关键步骤是三个钯催化的反应，炔烃的氢化锡烷基化反应，Kosugi-Migita-Stille交叉偶联反应和还原性N-杂环化反应。
• Concise Syntheses of Marine (Bis)indole Alkaloids Meridianin C, D, F, and G and Scalaridine A via One-Pot Masuda Borylation-Suzuki Coupling Sequence
  作者：Marco Kruppa、Gereon A. Sommer、Thomas J. J. Müller

  DOI：10.3390/molecules27072233

  日期：——

  with (di)azine halides in a sequentially Pd-catalyzed one-pot fashion, i.e., by Masuda borylation–Suzuki coupling (MBSC) sequence. This methodology was successfully applied to the concise syntheses of marine indole alkaloids meridianin C, D, F, and G, as well as to the bisindole alkaloid scalaridine A, which were obtained in moderate to excellent yield.

  N-保护的3-碘吲哚与(二) 吖嗪卤化物以顺序Pd 催化的一锅方式反应，即通过Masuda 硼化-铃木偶联(MBSC) 序列。该方法成功地应用于海洋吲哚生物碱经络素C、D、F和G的简合成，以及双吲哚生物碱scalaridine A的简合成，获得了中等至优异的收率。
• Synthesis of scalaridine A
  作者：Se Hun Kim、Jonathan Sperry

  DOI：10.1016/j.tetlet.2015.09.033

  日期：2015.10

  A synthesis of the pyridine-linked bisindole alkaloid scalaridine A is described. An iridium catalyzed, directed C-H borylation of N-Boc-5-methoxyindole gave the corresponding 3-borylindole, which underwent a one-pot, double Suzuki-Miyaura cross-coupling reaction with 3,5-dibromopyridine to install the entire heteroaromatic framework of the natural product. Removal of the protecting groups gave a synthetic sample of scalaridine A, which was spectroscopically identical to that described in the isolation report. (C) 2015 Elsevier Ltd. All rights reserved.
• Insight into Copper Catalysis: In Situ Formed Nano Cu₂O in Suzuki–Miyaura Cross-Coupling of Aryl/Indolyl Boronates
  作者：Ganapathy Ranjani、Rajagopal Nagarajan

  DOI：10.1021/acs.orglett.7b01669

  日期：2017.8.4

  aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine

  已经研究了无配体铜催化3,5-二碘吡啶与芳基和吲哚硼酸酯的Suzuki-Miyaura偶联，收率良好。原位生成的纳米铜的2从氯化亚铜ø 2在反应条件下已经发现首次。通过5-碘嘧啶，碘吡啶，碘苯和二碘苯的芳基化进一步证明了反应的一般性，并产生了良好至中等的收率。此外，双吲哚生物碱Scalaridine A已成功地以60％的总收率合成。