7,8-dimethyl-3-phenylquinoline | 1373117-74-8

• 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: 7,8-dimethyl-3-phenylquinoline
• 英文别名: 7,8-Dimethyl-3-phenylquinoline
• CAS: 1373117-74-8
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: FVBSQXCJOMYJNS-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：

  苯甲醯亞胺酸 、 7,8-dimethyl-3-phenylquinoline 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三甲基乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以93%的产率得到2-((7-methyl-3-phenylquinolin-8-yl)methylamino)benzaldehyde
  参考文献：
  名称：

  温和条件下用蒽进行Rh催化的未活化C（sp3）-H键与氨基的直接胺化

  摘要：

  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。

  DOI：

  10.1002/chem.201602556
• 作为产物：
  描述：

  2-苯基-1,3-丙二醇 、 2,3-二甲基苯胺 在 四氟硼酸-二乙醚络合物 、 {[(PCy₃)(CO)RuH]₄(μ-O)(μ-OH)₂} 、 环戊烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以60%的产率得到7,8-dimethyl-3-phenylquinoline
  参考文献：
  名称：

  芳胺与1,2-和1,3-二元醇脱水CH偶联反应催化合成取代的吲哚和喹啉

  摘要：

  The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted, quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byprodficts.

  DOI：

  10.1021/acs.organomet.6b00273

文献信息

• Aerobic Synthesis of Substituted Quinoline from Aldehyde and Aniline: Copper-Catalyzed Intermolecular C–H Active and C–C Formative Cyclization
  作者：Rulong Yan、Xingxing Liu、Congming Pan、Xiaoqiang Zhou、Xiaoni Li、Xing Kang、Guosheng Huang

  DOI：10.1021/ol402312h

  日期：2013.9.20

  An efficient method for the direct synthesis of substituted quinolines from anilines and aldehydes through C–H functionalization, C–C/C–N bond formation, and C–C bond cleavage has been developed. The method is simple and practical and employs air as an oxidant.

  已经开发了一种通过C–H官能化，C–C / C–N键形成和C–C键裂解从苯胺和醛直接合成取代喹啉的有效方法。该方法简单实用，并采用空气作为氧化剂。
• 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.
• Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C–H Coupling of Arylamines with 1,2- and 1,3-Diols
  作者：Hanbin Lee、Chae S. Yi

  DOI：10.1021/acs.organomet.6b00273

  日期：2016.6.13

  The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted, quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byprodficts.
• 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。