4-(溴甲基)-1-甲基-2(1H)-喹啉酮 | 91348-39-9

• 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
• 中文名称: 4-(溴甲基)-1-甲基-2(1H)-喹啉酮
• 英文名称: 4-bromomethyl-1-methylquinolin-2(1H)-one
• 英文别名: 4-(bromomethyl)-1-methylquinolin-2(1H)-one；4-(bromomethyl)-1-methylquinolin-2-one
• CAS: 91348-39-9
• 化学式: C₁₁H₁₀BrNO
• 分子量: 252.11
• InChiKey: IVUHMFZSWMBJOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(溴甲基)-1-甲基-2(1H)-喹啉酮 在 potassium carbonate 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 4-[(2-Bromo-4-methylphenyl)sulfonylmethyl]-1-methylquinolin-2-one
  参考文献：
  名称：

  Regioselective Synthesis of 2H‐Benzothiopyrano[3,2‐c]quinolin‐7(8H)‐ones by Tri‐n‐butyltinhydride–Mediated Radical Cyclization

  摘要：

  A number of hitherto unreported2H-benzothiopyrano[3,2-c]quinolin-7(8H)-ones have been regioselectively synthesized in 90-96% yield by tri-n-butyltinhydride-AIBN-mediated radical cyclization from 4-(20-bromothioarylmethyl)1-methylquinolin- 2(1H)-ones and their corresponding sulfones. 4-(20-Bromothioarylmethyl) quinolin-2(1H)-ones were in turn prepared from 4-bromomethylquinolin2(1H)-one and o-bromothiophenols by refluxing in acetone in the presence of anhydrous K2CO3. These were converted to the corresponding sulfones by oxidation with two equivalents of m-CPBA in refluxing dichloromethane for 1 h.

  DOI：

  10.1080/00397910701266182
• 作为产物：
  描述：

  1,4-二甲基喹啉酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以70%的产率得到4-(溴甲基)-1-甲基-2(1H)-喹啉酮
  参考文献：
  名称：

  通过自由基环化形成碳-碳键：通过 nBu3SnH 介导反应区域选择性合成螺杂环化合物

  摘要：

  摘要 通过 n Bu3SnH-AIBN 介导的 4-(2'-溴芳氧基甲基)-1-甲基喹啉-2(1H)-酮在氮气下回流苯中自由基环化反应 4 小时，区域选择性地合成了几种螺杂环化合物。

  DOI：

  10.1080/00397910600602602

文献信息

• Direct Difluoromethylation of Heterocycles through Photosensitized Electron Transfer
  作者：Peng Dai、Chenxiao Li、Yufei Li、Yuchuan Zhu、Peng Teng、Yu‐Cheng Gu、Wei‐Hua Zhang

  DOI：10.1002/ejoc.202100896

  日期：2022.1.11

  A highly efficient, transition metal- and oxidant-free, direct C(sp2)-H difluoromethylation of heterocycles through visible light-induced electron transfer was developed. The reaction afforded difluoromethyl heterocycles by only using photoexcited diacetyl. The reaction showed a broad substrate tolerance and gave the products in good yields. Moreover, the representative products exhibited potential

  通过可见光诱导的电子转移，开发了一种高效、无过渡金属和氧化剂的杂环直接 C(sp 2 )-H 二氟甲基化。该反应仅通过使用光激发的二乙酰提供二氟甲基杂环。该反应显示出广泛的底物耐受性，并以良好的产率得到产物。此外，代表性产品表现出潜在的药物活性和良好的抗真菌活性。
• Carbostyril derivatives and antiallergic agent
  申请人：Sawai Pharmaceutical Co., Ltd.

  公开号：US05457099A1

  公开（公告）日：1995-10-10

  1. A compound of the formula: ##STR1## wherein the symbol of a solid line with a broken line means a single bond or a double bond, R and R' are independently selected from the group consisting of hydrogen atom, halogen atom, lower alkyl, nitro, unsubstituted amino and substituted amino, A and B are independently selected from the group consisting of hydrogen atom, lower alkyl optionally substituted with a lower cycloalkyl, aryl optionally substituted with one or more halogen atoms and the group: -Y-R.sup.2 wherein Y is lower alkylene and R.sup.2 is the group: ##STR2## wherein m is integer of 1 to 3, n is 0 or 1, Z is >N-, >CH-- or >C=, R.sup.3 is diaryl (lower) alkyl optionally substituted with one or more halogen atoms or is condensed heterocyclic group optionally substituted with oxo, with the proviso that (a) at least one of A and B is the group -Y-R.sup.2 and (b) when A is hydrogen atom and B is the group -Y-R.sup.2, then Z is >CH-- or >C= if R.sup.3 is condensed heterocyclic group optionally substituted with oxo and n is O or a pharmaceutically acceptable salt thereof. The compounds of the above formula have antiallergic activity.

  该化合物的结构式如下：##STR1##其中实线和虚线表示单键或双键，R和R'分别选自氢原子、卤素原子、低烷基、硝基、未取代氨基和取代氨基的群体，A和B分别选自氢原子、可选择用低环烷基取代的低烷基、可选择用一个或多个卤素原子取代的芳基以及该群体：-Y-R.sup.2，其中Y为低烷基，R.sup.2为该群体：##STR2##其中m为1至3的整数，n为0或1，Z为>N-、>CH--或>C=，R.sup.3为可选择用一个或多个卤素原子取代的二芳基（低）烷基或是可选择用氧代取代的缩杂环基团，但须满足(a)至少一个A和B为该群体-Y-R.sup.2，以及(b)当A为氢原子且B为该群体-Y-R.sup.2时，若R.sup.3为可选择用氧代取代的缩杂环基团且n为0，则Z为>CH--或>C=或其药用盐。上述结构的化合物具有抗过敏活性。
• Visible-Light-Induced Dehydrohalogenative Coupling for Intramolecular α-Alkenylation: A Way to Build Seven- and Eight-Membered Rings
  作者：Dawen Xu、Han Li、Guangxing Pan、Pan Huang、Jens Oberkofler、Robert M. Reich、Fritz E. Kühn、Hao Guo

  DOI：10.1021/acs.orglett.0c01391

  日期：2020.6.5

  with cyclobutane and cyclobutene being involved as key intermediates. This transformation is broadly applicable and highly stereoselective, yielding exclusively cyclic (1Z,3Z)-1,3-diene via photochemically allowed disrotation. This protocol excavates new applications of [2 + 2]-photocycloadditions, which may find their way in future olefin–olefin coupling reactions and medium-sized ring synthesis.

  可见光诱导的分子内α-烯基化反应是通过无金属的脱卤化氢的C（sp 2）–C（sp 2）偶联反应发展而得到的七元和八元环。广泛的机理研究证明，该反应通过[2 + 2]-光环加成，消除和逆-[2 + 2]-光环加成过程进行，其中环丁烷和环丁烯为关键中间体。这种转换具有广泛的应用范围和高度立体选择性，仅产生环状（1 Z，3 Z）-1,3-二烯经光化学作用允许旋转。该协议开辟了[2 + 2]-光环加成的新应用，它们可能会在未来的烯烃-烯烃偶联反应和中型环合成中找到应用。
• Regioselective synthesis of bioactive spiro heterocyclic compounds containing both indoline and quinolone moieties by aryl radical cyclization
  作者：K. C. Majumdar、N. Kundu

  DOI：10.1002/jhet.101

  日期：2009.5

  The tin hydride-mediated aryl radical cyclization of a number of 4-(2′-bromo-N-methylanilino)methyl-1-alkylquinolin-2(1H)-ones under mild neutral condition afforded 1-alkyl-3,4-dihydroquinolin-2(1H)-one-4-spiro-3′-(1-methylindolines) in excellent yield. The starting materials, amines were derived from 4-bromomethyl-N-methyl quinolin-2(1H)-ones and 2-bromo-N-methyl anilines by refluxing in acetone in

  在温和的中性条件下，一些4-（2'-溴-N-甲基苯胺基）甲基-1-烷基喹啉-2（1 H）-的氢化锡介导的芳基自由基环化得到1-烷基-3,4-二氢喹啉-2（1 H）-一-4-螺-3'-（1-甲基二氢吲哚），收率极高。通过在无水存在下在丙酮中回流，从4-溴甲基-N-甲基喹啉-2（1 H）-酮和2-溴-N-甲基苯胺衍生原料胺。碳酸钾和碘化钠（Finkelstein条件）。J.杂环化​​学。，46，492（2009）。
• An efficient synthesis of benzo[b]benzofurano[2,3-e]-[1,6]naphthyridine-8-ones
  作者：Dao-Lin Wang、Dan Wu、Wei Zhao、Yong-Yang Wang、Jian-Ying Wu

  DOI：10.1016/j.cclet.2014.11.005

  日期：2015.2

  An efficient method for the synthesis of benzo[b]benzofurano[2,3-e][1,6]naphthyridine-8-one derivatives has been developed via Pictet-Spengler reaction of 4-(3-aminobenzofuran-2-yl)quinoline-2-ones, which could be obtained from alkylation of 4-bromomethylquinoline-2-ones with salicylonitrile and subsequent Thorpe-Ziegler isomerization, with aromatic aldehydes under p-TsOH as catalyst in good yields. (C) 2014 Dao-Lin Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.