6-methyl-2-phenethylquinoline | 1336877-37-2

• 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: 6-methyl-2-phenethylquinoline
• 英文别名: 6-Methyl-2-(2-phenylethyl)quinoline；6-methyl-2-(2-phenylethyl)quinoline
• CAS: 1336877-37-2
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: FTWWPZSEXFOJCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-benzyl-3-ethoxycyclobutanone 、 乙烷,三氯氟- 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到6-methyl-2-phenethylquinoline
  参考文献：
  名称：

  通过[3 + 3]在室温下3-乙氧基环丁酮和芳香胺之间的环化反应，轻松合成取代的2-烷基喹啉

  摘要：

  描述了一种有效的一步法合成2-烷基喹啉。通过路易斯酸介导的3-乙氧基环丁酮与芳族胺之间的[3 + 3]环化反应，在室温下区域选择性地制备了多种多取代的2-烷基喹啉衍生物。

  DOI：

  10.1021/ol202334s

文献信息

• Cobalt-catalyzed alkylation of methyl-substituted N-heteroarenes with primary alcohols: direct access to functionalized N-heteroaromatics
  作者：Anju Mishra、Ambikesh D. Dwivedi、Sujan Shee、Sabuj Kundu

  DOI：10.1039/c9cc08448g

  日期：——

  Phosphine free, air and moisture stable Co(NNN) complex catalyzed alkylation of various methyl-substituted N-heteroarenes with alcohols is reported. Following the borrowing hydrogen methodology, a variety of methyl-substituted N-heteroarenes can be functionalized efficiently. To understand the mechanism of this reaction various kinetic and control experiments were carried out.

  据报道，无磷，空气和水分稳定的Co（NNN）络合物催化了各种甲基取代的N-杂芳烃与醇的烷基化反应。遵循借用氢方法，可以有效地官能化各种甲基取代的N-杂芳烃。为了理解该反应的机理，进行了各种动力学和控制实验。
• Manganese catalyzed C-alkylation of methyl <i>N</i>-heteroarenes with primary alcohols
  作者：Akash Jana、Amol Kumar、Biplab Maji

  DOI：10.1039/d1cc00181g

  日期：——

  C-Alkylations of nine different classes of methyl-substituted N-heteroarenes, including quinolines, quinoxalines, benzimidazoles, benzoxazoles, pyrazines, pyrimidines, pyridazines, pyridines, and triazines are disclosed. A bench stable earth-abundant Mn(I)-complex catalyzed the chemoselective hydrogen-transfer reaction utilizing a diverse range of primary alcohols as the non-fossil fuel-derived carbon

  公开了九种不同类别的甲基取代的N-杂芳烃的C-烷基化，包括喹啉，喹喔啉，苯并咪唑，苯并恶唑，吡嗪，嘧啶，哒嗪，吡啶和三嗪。台式稳定的富含地球的Mn（I）络合物利用多种伯醇作为非化石燃料衍生的碳源，催化化学选择性氢转移反应。以高收率和选择性分离出多样化的N-杂芳烃（41个实例）。水是唯一的副产物，使该方案对环境无害。
• Ligand-Free RuCl₃-Catalyzed Alkylation of Methylazaarenes with Alcohols
  作者：Tong-Yu Feng、Hong-Xi Li、David James Young、Jian-Ping Lang

  DOI：10.1021/acs.joc.6b03095

  日期：2017.4.21

  RuCl3 efficiently catalyzes the alkylation of methylquinolines, methylpyridines, 2-methyl-benzooxazoles, and 2-methyl-quinoxalines with alkyl- or aryl-alcohols as alkylating agents. This synthetically useful and atom economical transformation does not require additional ligands. The mechanistic study indicated the alkylation reaction underwent a stepwise transfer hydrogenation, aldol condensation,

  RuCl 3以烷基或芳基醇作为烷基化剂有效地催化甲基喹啉，甲基吡啶，2-甲基-苯并恶唑和2-甲基-喹喔啉的烷基化。这种在合成上有用且原子经济的转变不需要其他配体。机理研究表明，烷基化反应经历了逐步转移的氢化，醛醇缩合和氢化反应路径。
• Phosphine‐Free <i>NNN</i>‐Manganese(II) Catalyzed C‐alkylation of Methyl <i>N</i>‐Heteroarenes via Borrowing Hydrogen
  作者：Qiang Rong、Xiaojing Li、Nan Sun、Baoxiang Hu、Xinquan Hu、Liqun Jin

  DOI：10.1002/adsc.202301291

  日期：2024.4.9

  Mn(II)‐catalyzed alkylations of methyl N‐heteroarenes was reported via borrowing hydrogen strategy with alcohols as the alkylating reagent. The developed geometry‐constrained benzimidazole‐iminopyridyl ligand played a key role in promoting the transformation and stablizing the metal center. A wide range of alcohols (aromatic, heteroaromatic and aliphatic) and methyl N‐Heteroarenes could be able to apply in the current catalytic system, with TON up to 7400.

  摘要 通过借氢策略，以醇为烷基化试剂，报道了锰(II)催化甲基 N-异戊二烯的烷基化反应。所开发的几何约束苯并咪唑-亚氨基吡啶配体在促进转化和稳定金属中心方面发挥了关键作用。多种醇类（芳香族、杂芳香族和脂肪族）和甲基 N-杂环戊烯都可以应用于当前的催化体系，催化活性可达 7400。
• A Facile Synthesis of Substituted 2-Alkylquinolines through [3 + 3] Annulation between 3-Ethoxycyclobutanones and Aromatic Amines at Room Temperature
  作者：Gang Shan、Xiuyun Sun、Qian Xia、Yu Rao

  DOI：10.1021/ol202334s

  日期：2011.11.4

  An efficient single-step approach toward the synthesis of 2-alkylquinolines is described. Through a Lewis acid mediated [3 + 3] annulation reaction between 3-ethoxycyclobutanones and aromatic amines, a variety of multisubstituted 2-alkylquinoline derivatives were prepared regioselectively at room temperature.

  描述了一种有效的一步法合成2-烷基喹啉。通过路易斯酸介导的3-乙氧基环丁酮与芳族胺之间的[3 + 3]环化反应，在室温下区域选择性地制备了多种多取代的2-烷基喹啉衍生物。