9-bromo-6H-chromeno[4,3-b]quinolin-6-one | 947380-45-2

• 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: 9-bromo-6H-chromeno[4,3-b]quinolin-6-one
• 英文别名: 9-bromochromeno[4,3-b]quinolin-6-one
• CAS: 947380-45-2
• 化学式: C₁₆H₈BrNO₂
• 分子量: 326.149
• InChiKey: QRKHEIJEYMIDDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-bromo-6H-chromeno[4,3-b]quinolin-6-one 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.33h， 生成 6-甲基香豆素
  参考文献：
  名称：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

  摘要：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities. (C) 2012 E Tang. Published by Elsevier B.V on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.022
• 作为产物：
  描述：

  4-methylphenyl cinnamate 在 三氟甲磺酸三甲基硅酯 、 9-bromo-6H-chromeno[4,3-b]quinolin-6-one 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 9-bromo-6H-chromeno[4,3-b]quinolin-6-one
  参考文献：
  名称：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

  摘要：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities. (C) 2012 E Tang. Published by Elsevier B.V on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.022
• 作为试剂：
  描述：

  4-methylphenyl cinnamate 在 三氟甲磺酸三甲基硅酯 、 9-bromo-6H-chromeno[4,3-b]quinolin-6-one 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 9-bromo-6H-chromeno[4,3-b]quinolin-6-one
  参考文献：
  名称：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

  摘要：

  TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality, followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities. (C) 2012 E Tang. Published by Elsevier B.V on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.03.022

文献信息

• Electrooxidative Metal‐Free Cyclization of 4‐Arylaminocoumarins with DMF as C1‐Source
  作者：Yiyi Weng、Hantao Chen、Nanhui Li、Long Yang、Lutz Ackermann

  DOI：10.1002/adsc.202100146

  日期：2021.6.8

  An environmentally-benign electrochemical approach for the construction of quinoline derivatives employing N,N-dimethylformamide (DMF) as the methine source has been devised by cyclization of 4-(phenylamino)-2H-chromen-2-ones. In a user-friendly undivided cell, 6H-chromeno[4,3-b]quinolin-6-ones were obtained under chemical oxidant-free and transition-metal-free conditions in 43–92% yields with high

  已经通过 4-(苯基氨基) -2H -chromen-2-ones的环化设计了一种环境友好的电化学方法，用于构建使用N，N-二甲基甲酰胺 (DMF) 作为次甲基源的喹啉衍生物。在用户友好的无隔膜电解槽，6H -chromeno [4,3- b ]喹啉-6-酮进行化学氧化剂-自由和过渡金属-自由条件下在具有高功能性公差43-92％的产率获得。
• NH ₄ OAc‐Promoted Cascade Approach towards Aberrant Synthesis of Chromene‐Fused Quinolinones
  作者：Santosh Kumari、S. M. Abdul Shakoor、Datta Markad、Sanjay K. Mandal、Rajeev Sakhuja

  DOI：10.1002/ejoc.201801292

  日期：2019.1.31

  A concise cascade, metal‐free strategy for the synthesis of chromene‐fused quinolinones was developed. This strategy is scalable, and an array of arylhydrazine hydrochlorides delivered chromene‐fused quinolinones in good to excellent yields.

  开发了一种简洁的级联，无金属的苯并二甲基吡啶基喹啉酮合成方法。这种策略是可扩展的，并且一系列芳基肼盐酸盐能够以优异的产率提供色烯稠合的喹啉酮。
• Iron/acetic acid mediated intermolecular tandem C–C and C–N bond formation: an easy access to acridinone and quinoline derivatives
  作者：R. R. Rajawinslin、Sachin D. Gawande、Veerababurao Kavala、Yi-Hsiang Huang、Chun-Wei Kuo、Ting-Shen Kuo、Mei-Ling Chen、Chiu-Hui He、Ching-Fa Yao

  DOI：10.1039/c4ra06410k

  日期：——

  An efficient iron/acetic acid mediated one pot reductive cyclization protocol was successfully developed for the synthesis of acridinone and quinoline derivatives.

  一种高效的铁/醋酸介导的一锅式还原环化方案成功开发，用于合成吖啶酮和喹啉衍生物。
• Solvent- and Catalyst-Free Synthesis of 6<i>H</i>-Chromeno [4,3-<i>b</i>]quinolin-6-ones
  作者：Prasanta Patra

  DOI：10.1080/00304948.2020.1868911

  日期：2021.3.4

  (2021). Solvent- and Catalyst-Free Synthesis of 6H-Chromeno [4,3-b]quinolin-6-ones. Organic Preparations and Procedures International: Vol. 53, No. 2, pp. 184-189.

  （2021年）。6H-Chromeno [4,3-b] quinolin-6-ones的无溶剂和无催化剂合成。国际有机制剂和程序：Vol。53，第2号，第184-189页。
• An efficient ultrasound promoted catalyst-free protocol for the synthesis of chromeno[4,3-b]quinolin-6-ones
  作者：J VENKATA PRASAD、J SATYANARAYANA REDDY、N RAVI KUMAR、K ANAND SOLOMON、G GOPIKRISHNA

  DOI：10.1007/s12039-011-0134-z

  日期：2011.9

  A convenient, catalyst-free protocol for the quantitative synthesis of fused chromeno[4,3-b]quinolin-6-ones has been developed by simple one-pot reaction of substituted anilines with 4-chloro-3-formylcoumarin using ultrasound irradiation. The protocol offers the advantages of mild reaction conditions, short reaction times and high yields.

  通过简单的分步反应将取代苯胺与4-氯-3-醛基香豆素在超声波照射下进行融合，开发了一种无需催化剂的方便程序，用于定量合成融合色烯[4,3-b]喹啉-6-酮。该方案具有反应条件温和、反应时间短和产率高的优点。