5,8-dimethyl-3-phenylquinoline | 1373117-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5,8-dimethyl-3-phenylquinoline
• CAS: 1373117-75-9
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: JDJLKCRTKOSYGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,8-dimethyl-3-phenylquinoline 在 N-氯代丁二酰亚胺 、 palladium diacetate 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以81%的产率得到5-methyl-8-(nitromethyl)-3-phenylquinoline
  参考文献：
  名称：

  一种合成8-(硝基甲基)喹啉类化合物的方法

  摘要：

  本发明提供了一种合成8‑(硝基甲基)喹啉类化合物的方法：以8‑甲基喹啉类化合物为原料，与催化剂和硝化试剂加入有机溶剂中，密闭加热至80‑130℃反应，TLC跟踪至反应结束后，反应液后处理制得式II所示的8‑(硝基甲基)喹啉类化合物。本发明的硝化方法具有硝化位置专一性的优点，只在甲基上硝化，而没有苯环上硝化产物的生成，反应过程安全环保、底物适应性好，各种取代基都可以实现甲基硝化；直接以8‑甲基喹啉为原料，反应步骤简单，是一种合成各种含取代基的8‑(硝基甲基)喹啉类化合物的新路线。

  公开号：

  CN104860880B
• 作为产物：
  描述：

  2,5-二甲基苯胺 、 2-phenylglycerol 在 硫酸 、 sodium iodide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 5,8-dimethyl-3-phenylquinoline
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Intermolecular Amidation with Azides via C(sp³)–H Functionalization

  摘要：

  The amidation reactions of 8-methylquinolines with azides catalyzed by a cationic rhodium(III) complex proceed efficiently to give quinolin-8-ylmethanamine derivatives in good yields via C(sp(3))-H bond activation under external oxidant-free conditions. A catalytically competent five-membered rhodacycle has been isolated and characterized, revealing a key intermediate in the catalytic cycle.

  DOI：

  10.1021/jo5008515

文献信息

• Rh-Catalyzed Direct Amination of Unactivated C(sp³ )−H bond with Anthranils Under Mild Conditions
  作者：Conghui Tang、Miancheng Zou、Jianzhong Liu、Xiaojin Wen、Xiang Sun、Yiqun Zhang、Ning Jiao

  DOI：10.1002/chem.201602556

  日期：2016.8.1

  C−N Bond formation is of great significance due to the ubiquity of nitrogen‐containing compounds. Here, a mild and efficient RhIII‐catalyzed C(sp3)−H aryl amination reaction is reported. Anthranil is employed as the nitrogen source with 100 % atom efficiency. This C−H amination reaction exhibits broad substrate scope without using any external oxidants. Mechanistic studies including rhodacycle intermediates

  由于含氮化合物的普遍存在，C N键的形成具有重要意义。在这里，报告了温和有效的Rh III催化的C（sp 3）-H芳基胺化反应。蒽被用作氮源，原子效率为100％。这种CH氨基化反应在不使用任何外部氧化剂的情况下具有广泛的底物范围。介绍了机理研究，包括Rhodacycle中间体，H-D交换，动力学同位素效应（KIE）实验和原位IR。
• Rhodium(III)-Catalyzed Alkenylation Reactions of 8-Methylquinolines with Alkynes by C(sp³)H Activation
  作者：Bingxian Liu、Tao Zhou、Bin Li、Shansheng Xu、Haibin Song、Baiquan Wang

  DOI：10.1002/anie.201310711

  日期：2014.4.14

  The alkenylation reactions of 8‐methylquinolines with alkynes, catalyzed by [Cp*RhCl2}2], proceeds efficiently to give 8‐allylquinolines in good yields by C(sp3)H bond activation. These reactions are highly regio‐ and stereoselective. A catalytically competent five‐membered rhodacycle has been structurally characterized, thus revealing a key intermediate in the catalytic cycle.

  的8-甲基喹啉与炔烃的烯基化反应，由[的Cp *的RhCl催化2 } 2 ]，可有效地进行由C（SP得到良好的收率8 allylquinolines 3） H键活化。这些反应具有高度的区域选择性和立体选择性。具有催化活性的五元罗丹环已在结构上得到了表征，从而揭示了催化循环中的关键中间体。
• Cobalt(III)‐Catalyzed, DMSO‐Involved, and TFA‐Controlled Regioselective C−H Functionalization of Anilines with Alkynes for Specific Assembly of 3‐Arylquinolines
  作者：Peiquan Zhang、Yurong Yang、Zhiyong Chen、Zhang Xu、Xuefeng Xu、Zhi Zhou、Xiyong Yu、Wei Yi

  DOI：10.1002/adsc.201801709

  日期：2019.6.18

  Herein, a novel cobalt(III)‐catalyzed and TFA‐controlled [3+2+1] cyclization of diverse anilines and terminal alkynes has been realized by using DMSO as both the solvent and the C1 source, which led to the specific synthesis of privileged 3‐arylquinolines in one pot and regioselectively. Mechanistic investigations revealed that this versatile transformation might be initiated with a C−H activation

  在此，通过使用DMSO作为溶剂和C 1来源，实现了新型的钴（III）催化和TFA控制的各种苯胺和末端炔烃的[3 + 2 + 1]环化反应，这导致了特定的合成在一锅中和区域选择性地排列特权3-芳基喹啉。机理研究表明，这种多用途转化可能是通过CH活化过程和以2-乙烯基苯甲胺类物质为活性中间体而引发的。
• Metal-Free, Ionic Liquid-Mediated Synthesis of Functionalized Quinolines
  作者：Jaideep B. Bharate、Sandip B. Bharate、Ram A. Vishwakarma

  DOI：10.1021/co500047w

  日期：2014.11.10

  An expedient and metal-free synthetic protocol for construction of substituted quinolines has been developed from anilines and phenylacetaldehydes using imidazolium cation-based ionic liquids as the reaction medium. Mechanistic analysis indicated that the reaction occurs through C-C and C-N bond formation to produce isolable 2,3-disubstituted quinoline intermediates, which undergo C-C bond cleavage to produce 3-substituted quinolines. The reaction proceeds smoothly with a range of functionalities in good to excellent yields. Advantages of this protocol include metal-free, environmentally friendly, recyclable reaction media, higher yields and shorter reaction times, and thus is promising for the efficient combinatorial synthesis of structurally diverse 2,3-disubstituted and 3-substituted quinolines.
• Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C–C Cleavage for the Synthesis of Quinolines
  作者：Yicheng Zhang、Min Wang、Pinhua Li、Lei Wang

  DOI：10.1021/ol300391t

  日期：2012.5.4

  A novel iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation has been developed. The reaction utilizes an inexpensive FeCl3 as promoter and is suitable for forming a variety of 3-aryiquinolines from the simple and readily available starting materials.