2-(p-tolyl)naphtho[2,3-b]furan-4,9-dione | 62452-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2-(p-tolyl)naphtho[2,3-b]furan-4,9-dione
• 英文别名: 2-(4-methylphenyl)naphtho[2,3-b]furan-4,9-dione；2-(4-methylphenyl)benzo[f][1]benzofuran-4,9-dione
• CAS: 62452-64-6
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: BSLQCUXBTYPZCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡啶 、 2-(p-tolyl)naphtho[2,3-b]furan-4,9-dione 在 iron(III) chloride 作用下， 以84 %的产率得到6-(4-methylbenzoyl)benzo[f]pyrido[2,1-a]isoindole-7,12-dione
  参考文献：
  名称：

  Fused Furan Moieties from Enol-like Compounds and β-Keto Sulfoxonium Ylides Involving sp² C–H Activation and Concomitant Tandem C–O Annulation

  摘要：

  DOI：

  10.1021/acs.orglett.3c01455
• 作为产物：
  描述：

  2-(4-methylphenyl)naphtho[1,2-b]furan-4,5-dione 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(p-tolyl)naphtho[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones

  摘要：

  Naphthofuroquinones are of great value in medicinal chemistry. In this letter, a facile method for highly regioselective synthesis of both linear and angular naphthofuroquinones has been developed via iodine mediated cyclization of 2-hydroxy-3-substitutedvinyl-1,4-naphthoquinones under very mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.058

文献信息

• Transition-Metal-Free One-Pot Synthesis of Naphthoquinonefuran Derivatives Through Sequential Nucleophilic Substitution–Nucleophilic Addition Reaction
  作者：Xiang Li、Peng Sun、Kaijun Xie、Dun Zhou、Jinsong Peng、Aihong Fan、Jing Zhang、Chunxia Chen

  DOI：10.1021/acs.joc.0c00513

  日期：2020.7.17

  naphthoquinonefuran derivatives from 2-hydroxynaphthoquinones has been developed. The sequentially accomplished process comprises an intermolecular alkynylation of sp2-carbon at the 3 position of 2-hydroxynaphthoquinones with arylethynyl bromides, followed by a base-promoted intramolecular nucleophilic annulation reaction. A broad range of functional groups is compatible with this reaction, and diverse naphtho[2

  已经开发了一种无过渡金属的路线，用于从2-羟基萘醌串联一锅法合成萘醌呋喃衍生物。依次完成的方法包括在2-羟基萘醌的3位上的sp 2-碳的分子间炔基化与芳基乙炔基溴化物，然后进行碱促进的分子内亲核环化反应。广泛的官能团与该反应相容，并且可以以良好的产率和优异的区域选择性获得各种萘并[2,3 - b ]呋喃-4,9-二酮。
• Photo-induced Reaction of 2-Alkoxy-3-bromo-1,4-naphthoquinones with Acetylenes: Formation of 2-Aryl-substituted Naphtho[2,3-<i>b</i>]furan-4,9-diones
  作者：Tetsuo Otsuki

  DOI：10.1246/bcsj.49.3713

  日期：1976.12

  2-Aryl-substituted naphtho[2,3-b]furan-4,9-diones 3 were obtained as a major product in the photo-chemical reaction of 2-alkoxy-3-bromo-1,4-naphthoquinones with acetylenes.

  2-芳基取代的萘并 [2,3-b] 呋喃-4,9-二酮 3 作为 2-烷氧基-3-溴-1,4-萘醌与乙炔的光化学反应的主要产物。
• An Efficient Synthesis of Naphtho[2,3-b]furan-4,9-diones via Visible-Light-Mediated [3+2] Cycloaddition Reaction
  作者：Hongbo Tan、Zehui Qi、Yuanhui Yu、Xu Zhang、Yuheng Xiang、Jingwen Huang、Zhigang Xu、Dianyong Tang、Zhongzhu Chen、Bochu Wang

  DOI：10.3390/molecules28124751

  日期：——

  Naphtho[2,3-b]furan-4,9-dione is an important privileged structural motif which is present in natural products, drugs, and drug candidates. Herein, visible-light-mediated [3+2] cycloaddition reaction for the synthesis of naphtho[2,3-b]furan-4,9-diones and dihydronaphtho[2,3-b]furan-4,9-diones has been developed. Under environmentally friendly conditions, a variety of title compounds were delivered

  萘并[2,3-b]呋喃-4,9-二酮是一种重要的特殊结构基序，存在于天然产物、药物和候选药物中。在此，用于合成萘并[2,3-b]呋喃-4,9-二酮和二氢萘并[2,3-b]呋喃-4,9-二酮的可见光介导的[3+2]环加成反应具有已开发。在环境友好的条件下，多种标题化合物均以良好的收率得到。这种新方案显示出优异的区域选择性和显着的官能团耐受性。该方法提供了一种强大、绿色、高效且简便的方法来扩大萘并[2,3-b]呋喃-4,9-二酮和二氢萘并[2,3-b]呋喃-4,9的结构多样性-二酮作为新药发现的有前途的支架。
• Visible-light-mediated synthesis, NMR analysis and X-ray crystal structure of naphtho[2,3-b]furan-4,9-diones
  作者：Hong-bo Tan、Xu Zhang、Yu-heng Xiang、Jing-wen Huang、Zhi-gang Xu、Dian-yong Tang、Zhong-zhu Chen、Bo-chu Wang

  DOI：10.1016/j.molstruc.2023.136140

  日期：2023.11

  An efficient, concise, and green visible-light-mediated [3 + 2] cycloaddition reaction for the diastereoselective synthesis of naphtho[2,3-b]furan-4,9-diones starting from readily available 2‑hydroxy-1,4-naphthoquinones and alkynes in the absence of any bases, metals, ligands, or other catalysts is described. The products could be obtained under blue LED (460 nm) irradiation at ambient temperature

  一种高效、简洁、绿色的可见光介导的[3 + 2]环加成反应，用于从容易获得的2-羟基-1,4开始非对映选择性合成萘并[2,3-b]呋喃-4,9-二酮描述了在不存在任何碱、金属、配体或其他催化剂的情况下的萘醌和炔烃。室温下在蓝色LED（460 nm）照射下6 h即可获得产物，具有完美的区域选择性和显着的官能团耐受性。该方法提供了一种新颖、强大、绿色、高效、简便的方法来扩展具有萘并[2,3-b]呋喃-4,9-二酮和二氢萘并[2,3- b ]结构基序的化合物的结构多样性。 ]呋喃-4,9-二酮作为新药发现的有前途的支架。
• The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones
  作者：Suyou Liu、Lijun Long、Duoduo Xie、Lijun Liu、Dayou Ma

  DOI：10.1016/j.tetlet.2015.10.058

  日期：2015.12

  Naphthofuroquinones are of great value in medicinal chemistry. In this letter, a facile method for highly regioselective synthesis of both linear and angular naphthofuroquinones has been developed via iodine mediated cyclization of 2-hydroxy-3-substitutedvinyl-1,4-naphthoquinones under very mild conditions. (C) 2015 Elsevier Ltd. All rights reserved.