6-cyclopropylquinoline | 1332365-30-6

• 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-cyclopropylquinoline
• CAS: 1332365-30-6
• 化学式: C₁₂H₁₁N
• 分子量: 169.226
• InChiKey: BTIJUXMNPMNBAN-UHFFFAOYSA-N

物化性质

• 沸点：
  307.9±11.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  6-cyclopropylquinoline 在 copper(l) iodide 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 6-cyclopropyl-2-(2-formylphenylamino)quinoline 1-oxide
  参考文献：
  名称：

  Copper-Catalyzed Direct, Regioselective Arylamination of N-Oxides: Studies To Access Conjugated π-Systems

  摘要：

  An efficient copper(I)-catalyzed direct regioselective arylamination of various heterocyclic N-oxides was achieved successfully under redox-neutral conditions using anthranils as arylaminating reagents. The developed protocol is simple, straightforward, and economic with a broad range substrate scope. The dual functional groups in the final molecules were utilized to construct structurally and functionally diverse nitrogen-containing organic x-conjugated systems.

  DOI：

  10.1021/acs.joc.7b01343
• 作为产物：
  描述：

  quinolin-6-yl methanesulfonate 、 环丙基三氟硼酸钾 在 potassium phosphate 、 dichloro(cycloocta-1,5-diene)palladium (II) 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 16.0h， 以85%的产率得到6-cyclopropylquinoline
  参考文献：
  名称：

  Cross-Coupling of Mesylated Phenol Derivatives with Potassium Cyclopropyltrifluoroborate

  摘要：

  C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%.

  DOI：

  10.1021/jo2015246

文献信息

• Copper-Catalyzed Regioselective Cascade Alkylation and Cyclocondensation of Quinoline <i>N</i> -Oxides with Diazo Esters: Direct Access to Conjugated π-Systems
  作者：Aniruddha Biswas、Ujjwal Karmakar、Arun Pal、Rajarshi Samanta

  DOI：10.1002/chem.201602493

  日期：2016.9.19

  An inexpensive copper‐catalyzed cascade regioselective alkylation, followed by cyclocondensation of quinoline N‐oxides with α‐diazo esters has been achieved successfully to provide heteroarene‐containing conjugated π‐systems. The developed method is simple, straightforward, and economical with a broad range of substrate scope. The dual role of copper catalyst in the C−H bond functionalization and in

  已经成功实现了廉价的铜催化级联区域选择性烷基化，然后将喹啉N-氧化物与α-重氮酯进行环缩合，从而提供了含杂芳烃的共轭π系统。所开发的方法简单，直接且经济，具有广泛的基板范围。探索了铜催化剂在CH键功能化和路易斯酸促进的环化中的双重作用。
• Copper-Catalyzed Direct, Regioselective Arylamination of <i>N</i>-Oxides: Studies To Access Conjugated π-Systems
  作者：Aniruddha Biswas、Ujjwal Karmakar、Shiny Nandi、Rajarshi Samanta

  DOI：10.1021/acs.joc.7b01343

  日期：2017.9.1

  An efficient copper(I)-catalyzed direct regioselective arylamination of various heterocyclic N-oxides was achieved successfully under redox-neutral conditions using anthranils as arylaminating reagents. The developed protocol is simple, straightforward, and economic with a broad range substrate scope. The dual functional groups in the final molecules were utilized to construct structurally and functionally diverse nitrogen-containing organic x-conjugated systems.
• Cross-Coupling of Mesylated Phenol Derivatives with Potassium Cyclopropyltrifluoroborate
  作者：Gary A. Molander、Floriane Beaumard、Terren K. Niethamer

  DOI：10.1021/jo2015246

  日期：2011.10.7

  C-O activation of mesylates by a palladium catalyst and subsequent cross-coupling with potassium cyclopropyltrifluoroborate have been achieved with high yield. Both electron-enriched and electron-deficient aryl mesylates are suitable electrophilic partners for the Suzuki-Miyaura reaction. The scope was successfully extended to heteroaryl mesylates with yields up to 94%.