1-(2-((4-methoxyphenyl)ethynyl)phenyl)-3-methyl-1H-indole | 1311312-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-((4-methoxyphenyl)ethynyl)phenyl)-3-methyl-1H-indole
• 英文别名: 1-[2-[2-(4-Methoxyphenyl)ethynyl]phenyl]-3-methylindole
• CAS: 1311312-58-9
• 化学式: C₂₄H₁₉NO
• 分子量: 337.421
• InChiKey: FTMUHZCKDRIMLW-UHFFFAOYSA-N

物化性质

• 沸点：
  464.3±45.0 °C(predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-((4-methoxyphenyl)ethynyl)phenyl)-3-methyl-1H-indole 在 sodium tetrahydroborate 、 copper(l) iodide 、 碘 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.67h， 生成 6-(4-methoxyphenyl)-7-methylindolo[1,2-a]quinoline
  参考文献：
  名称：

  Synthesis of 5-Iodopyrrolo[1,2-a]quinolines and Indolo[1,2-a]quinolines via Iodine-Mediated Electrophilic and Regioselective 6-endo-dig Ring Closure

  摘要：

  The endo-cyclic ring closure of 1-(2-(substituted ethynyl)pheny1)-1H-pyrroles 3a-t and 1-(2-(substituted ethynyl)phenyl)-H-indole 4a-o mediated by Lewis acid (I-2) under mild conditions afforded substituted 5-iodopyrrolo[1,2-a]quinolines 5a-t and 5-iodoindolo[1,2-a]quinolines 6a-o in good to excellent yields. The reaction shows selective C-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized product. Iodo derivatives of pyrrolo- and indoloquinolines allow functional group diversification on the quinoline nucleus, which proves to be highly advantageous for structural and biological activity assessments.

  DOI：

  10.1021/jo200638k
• 作为产物：
  描述：

  1,2-二碘苯 在 T406石油添加剂 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium phosphate 、 copper(l) iodide 、 三乙胺 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 16.0h， 生成 1-(2-((4-methoxyphenyl)ethynyl)phenyl)-3-methyl-1H-indole
  参考文献：
  名称：

  3-烷基-1-(2-(炔基)苯基)吲哚的级联氧化三氟甲基硫醇化和环化

  摘要：

  研究了过硫酸盐促进的自由基级联三氟甲基硫醇化和 3-烷基-1-(2-(炔基)苯基) 吲哚与 AgSCF 3的环化。该方案通过形成_ _ _ _ _ C-SCF 3键和 C-C 键和苄基碳氧化一步完成。该反应可以容纳范围广泛的官能团。单晶X射线衍射数据证实了产品的化学结构。在反应体系中进行放大实验和自由基抑制实验。一些选定的 5-((三氟甲基)硫代) 吲哚[1,2- a ] 喹啉-7-甲醛的光物理性质通过紫外-可见和荧光光谱进行了研究。

  DOI：

  10.1021/acs.joc.2c03045

文献信息

• Metal-free sulfonyl radical-initiated cascade cyclization to access sulfonated indolo[1,2-<i>a</i>]quinolines
  作者：Kai Sun、Xiao-Lan Chen、Yin-Li Zhang、Kai Li、Xian-Qiang Huang、Yu-Yu Peng、Ling-Bo Qu、Bing Yu

  DOI：10.1039/c9cc06924k

  日期：——

  A metal-free cascade reaction was developed for the synthesis of indolo[1,2-a]quinoline derivatives from arylsulfonyl hydrazides and 1-(2-(arylethynyl)phenyl)indoles in the presence of TBAI/TBHP. Impressively, these products exhibit excellent fluorescence properties, which is promising for cell imaging.

  开发了一种无金属级联反应，用于在TBAI / TBHP存在下由芳基磺酰基酰肼和1-（2-（芳基乙炔基）苯基）吲哚合成吲哚并[1,2- a ]喹啉衍生物。令人印象深刻的是，这些产品具有出色的荧光特性，有望用于细胞成像。
• Di(1H-benzo[d][1,2,3]triazol-1-yl)methane: An efficient ligand for copper and amine-free palladium-catalysed Sonogashira coupling reaction
  作者：JASPAL SINGH、AKHILESH KUMAR VERMA

  DOI：10.1007/s12039-011-0174-4

  日期：2011.11

  An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1H-benzo[d][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-defficient and hindered aryl halides with terminal alkynes afforded the internal alkynes in good to excellent yields.

  在不含铜和胺的情况下，使用无膦、空气稳定的二(1H-苯并[d][1,2,3]三唑-1-基)甲烷作为配体，配合高效钯催化的Sonogashira偶联反应，在无机碱存在下成功实现。富电子、缺电子及位阻的芳基卤化物与末端炔烃的交叉偶联反应，均能以良好至优异的产率得到内部炔烃。
• One‐Pot Gold/Acid‐Catalyzed Synthesis of Indolo[1,2‐<i>a</i>]quinolin‐5(6<i>H</i>)‐ones from 1‐(2‐Ethynylphenyl)‐1<i>H</i>‐indoles
  作者：Elisa Brambilla、Mariaclara Gugiatti、Silvia Rizzato、Giorgio Abbiati、Valentina Pirovano

  DOI：10.1002/ejoc.202400083

  日期：——

  The synthesis of substituted indolo[1,2-a]quinoline-5(6H)-ones starting from 1-(2-ethynylphenyl)-1H-indoles is presented. The method involves gold-catalyzed oxidation of the triple bond followed by an acid-promoted intramolecular cyclization at the indole C-2 position.

  提出了从 1-(2-乙炔基苯基)-1H-吲哚开始合成取代的吲哚并[1,2-a]喹啉-5(6H)-酮。该方法涉及金催化的三键氧化，然后在吲哚 C-2 位上进行酸促进的分子内环化。
• Visible-Light-Induced Intramolecular Tandem Cyclization of Unactivated Indoloalkynes for the Synthesis of Sulfonylated and Selenylated Indolo[1,2-<i>a</i>]quinolines
  作者：Shouren Zhang、Jinwei Yuan、Guangchao Huang、Chengjia Ma、Jingjing Yang、Liangru Yang、Yongmei Xiao、Lingbo Qu

  DOI：10.1021/acs.joc.3c00997

  日期：2023.8.18
• Synthesis of 5-Iodopyrrolo[1,2-<i>a</i>]quinolines and Indolo[1,2-<i>a</i>]quinolines via Iodine-Mediated Electrophilic and Regioselective 6-<i>endo</i>-<i>dig</i> Ring Closure
  作者：Akhilesh Kumar Verma、Satya Prakash Shukla、Jaspal Singh、Vineeta Rustagi

  DOI：10.1021/jo200638k

  日期：2011.7.15

  The endo-cyclic ring closure of 1-(2-(substituted ethynyl)pheny1)-1H-pyrroles 3a-t and 1-(2-(substituted ethynyl)phenyl)-H-indole 4a-o mediated by Lewis acid (I-2) under mild conditions afforded substituted 5-iodopyrrolo[1,2-a]quinolines 5a-t and 5-iodoindolo[1,2-a]quinolines 6a-o in good to excellent yields. The reaction shows selective C-C bond formation on the more electrophilic alkynyl carbon, resulting in the regioselective 6-endo-dig-cyclized product. Iodo derivatives of pyrrolo- and indoloquinolines allow functional group diversification on the quinoline nucleus, which proves to be highly advantageous for structural and biological activity assessments.