1-benzyloxycarbonyl-6-bromo-4-quinolone | 332366-39-9

• 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: 1-benzyloxycarbonyl-6-bromo-4-quinolone
• 英文别名: Benzyl 6-bromo-4-oxoquinoline-1-carboxylate
• CAS: 332366-39-9
• 化学式: C₁₇H₁₂BrNO₃
• 分子量: 358.191
• InChiKey: PTUKLVMMHTZKJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxycarbonyl-6-bromo-4-quinolone 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-benzyloxycarbonyl-6-bromo-2-(2-propenyl)-4-tri-iso-propylsilyloxy-2H-quinoline
  参考文献：
  名称：

  Efficient allylation of 4-silyloxyquinolinium triflates and other positively charged heteroaromatic systems

  摘要：

  The regioselective allylation of 4-silyloxyquinolinium triflates with allyltri-n-butyltin has been performed to give 2-allyl-4-silyloxy-1,2-dihydroquinolines with excellent yields. Similiar results have been obtained with 4-silyloxy-l-benzopyrylium triflates and 4-silyloxy-1-benzothiopyrylium triflates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01066-8
• 作为产物：
  描述：

  5-[(4-溴苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮 在 sodium hydride 作用下， 以 四氢呋喃 、 二苯醚 为溶剂， 反应 24.0h， 生成 1-benzyloxycarbonyl-6-bromo-4-quinolone
  参考文献：
  名称：

  Efficient allylation of 4-silyloxyquinolinium triflates and other positively charged heteroaromatic systems

  摘要：

  The regioselective allylation of 4-silyloxyquinolinium triflates with allyltri-n-butyltin has been performed to give 2-allyl-4-silyloxy-1,2-dihydroquinolines with excellent yields. Similiar results have been obtained with 4-silyloxy-l-benzopyrylium triflates and 4-silyloxy-1-benzothiopyrylium triflates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01066-8

文献信息

• Highly Enantioselective Catalytic Addition of Grignard Reagents to N‐Heterocyclic Acceptors
  作者：Yafei Guo、Syuzanna R. Harutyunyan

  DOI：10.1002/anie.201906237

  日期：2019.9.9

  greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2‐ and 4‐substituted tetrahydro‐quinolones, dihydro‐4‐pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.

  由于手性N-杂环分子支架在药物化学中的重要性，因此备受追捧。这里描述的是第一种通用催化方法，它利用单一催化剂系统，以优异的收率和对映选择性获得了各种手性2和4取代的四氢喹诺酮，二氢4吡啶酮和哌啶酮。
• Cu(I)-Catalyzed Alkynylation of Quinolones
  作者：Aitor Maestro、Sebastien Lemaire、Syuzanna R. Harutyunyan

  DOI：10.1021/acs.orglett.2c00020

  日期：2022.2.11
• Efficient allylation of 4-silyloxyquinolinium triflates and other positively charged heteroaromatic systems
  作者：Uwe Beifuss、Ursula Schniske、Gerald Feder

  DOI：10.1016/s0040-4020(00)01066-8

  日期：2001.2

  The regioselective allylation of 4-silyloxyquinolinium triflates with allyltri-n-butyltin has been performed to give 2-allyl-4-silyloxy-1,2-dihydroquinolines with excellent yields. Similiar results have been obtained with 4-silyloxy-l-benzopyrylium triflates and 4-silyloxy-1-benzothiopyrylium triflates. (C) 2001 Elsevier Science Ltd. All rights reserved.