10-(4-tert-butylphenyl)benzo[h]quinoline | 1270044-33-1

• 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: 10-(4-tert-butylphenyl)benzo[h]quinoline
• 英文别名: 10-(4-(tert-butyl)phenyl)benzo[h]quinoline
• CAS: 1270044-33-1
• 化学式: C₂₃H₂₁N
• 分子量: 311.426
• InChiKey: WHQMGXQOYLBSKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (benzo[h]quinolin-10-yl)methanol 、 4-叔丁基苯硼酸 在 Wilkinson's catalyst 、 copper(l) chloride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 15.0h， 以91%的产率得到10-(4-tert-butylphenyl)benzo[h]quinoline
  参考文献：
  名称：

  Efficient Approach To Construct Unsymmetrical Biaryls through Oxidative Coupling Reactions of Aromatic Primary Alcohols and Arylboronic Acids with a Rhodium Catalyst

  摘要：

  Unsymmetrical biaryls were synthesized by oxidative coupling reactions, between aromatic primary alcohols and arylboronic acids through the C-C bond cleavage of the primary alcohols chelated With a rhodium catalyst. The desired unsymmetrical biaryl products were obtained in good to excellent yields under the optimized reaction conditions. A wide variety of functionalities are compatible with the reaction under the optimized conditions. This new coupling strategy provides a favorable method to construct valuable biaryl compounds from aromatic primary alcohols which are cheap; environmentally friendly, and easily accessible substrates.

  DOI：

  10.1021/acs.organomet.6b00238

文献信息

• Direct Cross-Coupling of CH Bonds with Grignard Reagents through Cobalt Catalysis
  作者：Bin Li、Zhen-Hua Wu、Yi-Fan Gu、Chang-Liang Sun、Bai-Quan Wang、Zhang-Jie Shi

  DOI：10.1002/anie.201005394

  日期：2011.2.1

  Go go Grignard! The first highly regioselective, cobalt‐catalyzed CH transformation of benzo[h]quinoline and phenylpyridine derivatives with Grignard reagents at room temperature has been achieved (see scheme). Both aryl and alkyl Grignard reagents showed significant reactivity.

  快去格利雅（Grignard）！在室温下，使用格氏试剂首次实现了对苯并[ h ]喹啉和苯基吡啶衍生物的高区域选择性，钴催化的CH转化（参见方案）。芳基和烷基格氏试剂均显示出显着的反应性。
• Expeditious and Solvent-Free Nickel-Catalyzed C−H Arylation of Arenes and Indoles
  作者：Rahul A. Jagtap、Vineeta Soni、Benudhar Punji

  DOI：10.1002/cssc.201700321

  日期：2017.5.22

  nickel‐catalyzed method for C−H bond arylation of arenes and indoles has been developed, which proceeds expeditiously through chelation assistance. The reaction is highly selective for mono‐arylation and tolerates sensitive and structurally diverse functionalities, such as halides, ethers, amines, indole, pyrrole and carbazole. This reaction represents the first example of a nickel‐catalyzed C−H arylation by monochelate

  已经开发出一种有效的无溶剂镍催化的芳烃和吲哚CH键芳基化方法，该方法可通过螯合辅助快速进行。该反应对单芳基化反应具有高度选择性，并且可以耐受敏感的和结构多样的官能团，例如卤化物，醚，胺，吲哚，吡咯和咔唑。该反应代表单螯合物辅助镍催化的CH芳基化的第一个例子，并标志着无溶剂的CH H芳基化的罕见先例。通过各种受控反应，动力学研究和氘标记实验进行的机理研究表明，芳基化反应遵循单个电子转移（SET）途径，该途径涉及限制营业额的CH镍化过程。
• Rhodium-catalyzed decarbonylation cross-coupling reactions of aromatic aldehydes and arylboronic acids via C C bond activation directed by a guide group chelation
  作者：Xiaobo Yu、Guanchen Liu、Shudong Geng

  DOI：10.1016/j.inoche.2020.108065

  日期：2020.9

  Abstract A rhodium-catalyzed decarbonylative cross-coupling reaction of benzoquinoline-10-carbaldehydes with arylboronic acids through chelation-assisted sp2 C−CHO bond activation has been developed. A variety of functional groups substituted phenylboronic acids or benzoquinoline-10-carbaldehydes are compatible with the reaction under the optimized reaction conditions, the corresponding 10-phenylbenzo[h]quinoline

  摘要 已经开发了铑催化的苯并喹啉-10-甲醛与芳基硼酸通过螯合辅助 sp2 C-CHO 键活化的脱羰交叉偶联反应。在优化的反应条件下，多种官能团取代的苯基硼酸或苯并喹啉-10-甲醛与反应相容，相应的10-苯基苯并[h]喹啉衍生物以中等至良好的收率获得。该方法为通过铑催化的 sp2 C-CHO 键活化合成 N-杂环联芳基化合物提供了一种有用的策略。
• Ruthenium(II)-Catalyzed Chelation-Assisted Desulfitative Arylation of Benzo[h]quinolines with Arylsulfonyl Chlorides
  作者：Yi-Xin Xu、Yu-Qing Liang、Zhong-Jian Cai、Shun-Jun Ji

  DOI：10.1021/acs.orglett.2c00542

  日期：2022.4.15

  chelation-assisted C–H arylation reaction of benzo[h]quinoline is described. This transformation, using [RuCl2(p-cymene)]2 as the catalyst and cheap and easily accessible arylsulfonyl chlorides as the arylation source, featured simple reaction conditions, a broad substrate scope, and functional group tolerance. The successful application of some bioactive-molecule-based sulfonyl chlorides further highlighted

  在此，描述了苯并[h]喹啉的新型螯合辅助 C-H 芳基化反应。该转化以[RuCl 2 ( p -cymene)] 2为催化剂，廉价易得的芳基磺酰氯为芳基化源，具有反应条件简单、底物范围广、官能团耐受性高等特点。一些基于生物活性分子的磺酰氯的成功应用进一步突出了这种脱硫 C-H 芳基化方案的潜在用途和重要性。