2-((1s,3s)-adamantan-1-yl)-4-methylquinoline

• 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: 2-((1s,3s)-adamantan-1-yl)-4-methylquinoline
• 英文别名: 2-(adamantan-2-yl)-4-methylquinoline；2-(2-Adamantyl)-4-methylquinoline
• 化学式: C₂₀H₂₃N
• 分子量: 277.409
• InChiKey: QJFNEWKFKHYVSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-甲基喹啉 、 金刚烷 在 ammonium peroxydisulfate 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 以81%的产率得到2-((1s,3s)-adamantan-1-yl)-4-methylquinoline
  参考文献：
  名称：

  Cross-Dehydrogenative Coupling of Strong C(sp³)–H with N-Heteroarenes through Visible-Light-Induced Energy Transfer

  摘要：

  The sustainable cross-dehydrogenative coupling of strong C(sp(3))-H with N-heteroarenes has been developed using an efficient organic photocatalyst. It features atomic- and step-economy, and acid-free conditions. Mechanism studies suggest a previous elusive energy transfer pathway from photocatalyst to N-heteroarenes and oxidants.

  DOI：

  10.1021/acs.orglett.0c02912

文献信息

• Visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using O₂ as an oxidant
  作者：Jianyang Dong、Xueli Lyu、Zhen Wang、Xiaochen Wang、Hongjian Song、Yuxiu Liu、Qingmin Wang

  DOI：10.1039/c8sc04892d

  日期：——

  visible-light-mediated Minisci C–H alkylation of heteroarenes with unactivated alkyl halides using molecular oxygen as an oxidant at room temperature. This mild protocol is compatible with a wide array of sensitive functional groups and has a broad substrate scope. Notably, functionalization of (iso)quinolines, pyridines, phenanthrolines, quinazoline, and other heterocyclic compounds with unactivated primary, secondary

  在此，我们报告了一种在室温下使用分子氧作为氧化剂，用未活化的卤代烷对杂芳烃进行直接可见光介导的 Minisci C-H 烷基化的方案。这种温和的方案与多种敏感官能团兼容，并且具有广泛的底物范围。值得注意的是，（异）喹啉、吡啶、菲咯啉、喹唑啉和其他杂环化合物与未活化的伯、仲和叔烷基卤化物的官能化在标准条件下顺利进行。复杂的含氮天然产物和药物的后期功能化进一步证明了该协议的稳健性。
• Direct alkylation of heteroarenes with unactivated bromoalkanes using photoredox gold catalysis
  作者：T. McCallum、L. Barriault

  DOI：10.1039/c6sc00807k

  日期：——

  A protocol for direct C-H alkylation of heteroarenes was developed using photoredox catalysis as a mode of activation for unactivated bromoalkanes. Dimeric Au(I) complex, [Au2(dppm)2]Cl2, served as an efficient photocatalyst for this transformation.

  使用光氧化还原催化作为未活化溴代烷烃的活化方式，开发了用于杂芳烃直接CH烷基化的方案。二聚Au（I）络合物[Au 2（dppm）2 ] Cl 2充当了这种转化的有效光催化剂。
• Stop-Flow Microtubing Reactor-Assisted Visible Light-Induced Hydrogen-Evolution Cross Coupling of Heteroarenes with C(sp³)–H Bonds
  作者：Dong-Sheng Li、Tao Liu、Yang Hong、Chen-Lin Cao、Jie Wu、Hong-Ping Deng

  DOI：10.1021/acscatal.2c01087

  日期：2022.4.15

  feedstocks under mild conditions is attractive and highly desirable in pharmaceutical and natural product synthesis. Minisci-type cross dehydrogenative coupling between heteroarenes and C(sp3)–H bonds offers direct access to these important scaffolds in a step-economic manner. Herein, assisted by stop-flow microtubing reactors, an operationally simple protocol for the visible light-induced hydrogen-evolution

  在温和条件下从丰富且廉价的原料合成有价值的烷基取代的杂芳烃在药物和天然产物合成中具有吸引力和高度可取性。杂芳烃和 C(sp 3 )-H 键之间的 Minisci 型交叉脱氢偶联以逐步经济的方式提供了对这些重要支架的直接访问。在此，在停流微管反应器的辅助下，一种操作简单的协议，用于可见光诱导的杂芳烃与未活化 C(sp 3 ) 的析氢交叉耦合)–H 键以无金属和无外部氧化剂的方式形成。使用常见的原料化学品（包括乙烷）生成了范围广泛的烷基化杂芳烃。机理研究表明，光氧化还原诱导的氢原子转移过程，然后是脱氢重芳构化，提供了所需的偶联产物。各种复杂生物活性分子的后期功能化进一步证明了该策略的优点。
• Cross-Dehydrogenative Coupling of Strong C(sp³)–H with <i>N</i>-Heteroarenes through Visible-Light-Induced Energy Transfer
  作者：Haitao Tian、Hui Yang、Chao Tian、Guanghui An、Guangming Li

  DOI：10.1021/acs.orglett.0c02912

  日期：2020.10.2

  The sustainable cross-dehydrogenative coupling of strong C(sp(3))-H with N-heteroarenes has been developed using an efficient organic photocatalyst. It features atomic- and step-economy, and acid-free conditions. Mechanism studies suggest a previous elusive energy transfer pathway from photocatalyst to N-heteroarenes and oxidants.