3-methyl-1-(2-(thiophen-3-ylethynyl)phenyl)-1H-indole | 1311312-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-methyl-1-(2-(thiophen-3-ylethynyl)phenyl)-1H-indole
• 英文别名: 3-Methyl-1-[2-(2-thiophen-3-ylethynyl)phenyl]indole
• CAS: 1311312-62-5
• 化学式: C₂₁H₁₅NS
• 分子量: 313.423
• InChiKey: YSGWNYGZWKMKDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(2-(thiophen-3-ylethynyl)phenyl)-1H-indole 在 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到5-iodo-7-methyl-6-(thiophene-3-yl)indolo[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：

  3-甲基吲哚 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 3-methyl-1-(2-(thiophen-3-ylethynyl)phenyl)-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

• 2-(1-Benzotriazolyl)pyridine: A Robust Bidentate Ligand for the Palladium-Catalyzed CC (Suzuki, Heck, Fujiwara-Moritani, Sonogashira), CN and CS Coupling Reactions
  作者：Akhilesh K. Verma、Rajeev R. Jha、Ritu Chaudhary、Rakesh K. Tiwari、Abhinandan K. Danodia

  DOI：10.1002/adsc.201200583

  日期：2013.2.1

  designed and employed for the palladium-catalyzed CC (Suzuki, Heck, Fujiwara–Moritani, and Sonogashira), CN and CS coupling reactions. The ligand was found to be inexpensive, thermally stable, easy to synthesize from easily accessible starting materials on a multigram scale, show simplicity in use, and robustness in application, making this ligand effective for different coupling reactions. Suitably, the

  设计了一种新型的双齿配体1-（吡啶-2-基）-1 H-苯并[ d ] [1,2,3]三唑，并用于钯催化的CC（Suzuki，Heck，Fujiwara– Moritani和Sonogashira），CN和CS偶联反应。发现该配体便宜，热稳定，易于以几克规模由容易获得的起始原料合成，显示出使用简单性和在应用中的坚固性，从而使该配体对于不同的偶联反应有效。适当地，苯并三唑环的NN键的供体能力和吡啶环的N上的孤对电子增强了配体的二齿能力。
• 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。
• 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.
• Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles
  作者：Thikhamporn Uppalabat、Nattawoot Hassa、Natthapat Sawektreeratana、Pawaret Leowanawat、Pattarapapa Janthakit、Phattananawee Nalaoh、Vinich Promarak、Darunee Soorukram、Vichai Reutrakul、Chutima Kuhakarn

  DOI：10.1021/acs.joc.2c03045

  日期：2023.5.5

  trifluoromethylthiolation and cyclization of 3-alkyl-1-(2-(alkynyl)phenyl)indoles with AgSCF3 were investigated. This protocol provides a novel route to CF3S-substituted indolo[1,2-a]quinoline-7-carbaldehydes and CF3S-substituted indolo[1,2-a]quinoline-7-methanone derivatives via the formation of the C–SCF3 bond and C–C bond and benzylic carbon oxidation in a single step. This reaction can accommodate a broad

  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。