methyl 5-hydroxy-2-methylnaphtho[1,2-b]furan-4-carboxylate | 1342899-36-8

• 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: methyl 5-hydroxy-2-methylnaphtho[1,2-b]furan-4-carboxylate
• 英文别名: Methyl 5-hydroxy-2-methylbenzo[g][1]benzofuran-4-carboxylate；methyl 5-hydroxy-2-methylbenzo[g][1]benzofuran-4-carboxylate
• CAS: 1342899-36-8
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: GPWHVFGPKASSCN-UHFFFAOYSA-N

物化性质

• 沸点：
  409.2±40.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-2-methylnaphtho[1,2-b]furan-4-carboxylate 在 iron(III) chloride 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 70.75h， 生成
  参考文献：
  名称：

  通过1-甲硅烷氧基-1,4-环氧-1,4-二氢萘的位点选择性开环构建功能化邻萘醌甲基化物

  摘要：

  由苯炔和呋喃生成的1-甲硅烷氧基-4-(苄氧基)甲基-1,4-环氧-1,4-二氢萘由于1,4空间张力的协同作用而自动进行位点选择性开环-环氧部分和缩醛结构上甲硅烷氧基的给电子能力，提供邻萘醌甲基化物（o -NQMs）的前体。随后路易斯酸促进邻-NQM 形成并与烯烃成环，得到多稠合杂环。值得注意的是，rubioncolin B 的连续六环骨架是通过萘并呋喃衍生物的溶剂依赖性区域选择性成环构建的。

  DOI：

  10.1002/adsc.202300968
• 作为产物：
  描述：

  1,4-二羟基-2-萘甲酸甲酯 在 ammonium cerium (IV) nitrate 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 16.33h， 生成 methyl 5-hydroxy-2-methylnaphtho[1,2-b]furan-4-carboxylate 、 methyl 5-hydroxy-2-methoxy-2-methyl-2,3-dihydronaphtho [1,2-b]furan-4-carboxylate
  参考文献：
  名称：

  Antioxidant and antibacterial evaluation of synthetic furomollugin and its diverse analogs

  摘要：

  Diverse furomollugin (3) and its analogs (11-22) were synthesized in high yields via ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition as a key step. The in vitro antioxidant activities of synthesized compounds were determined by analyzing radical scavenging activities for 1,1-diphenyl-2-picrylhydrazyl (DPPH), nitric oxide, and hydrogen peroxide assays. The results showed that the synthesized furomollugin analogs had effective antioxidant power. Dihydronaphthofurans with 2-alkyoxy or 2-aryl group were the most potent radical scavengers in DPPH assay. Moreover, the antibacterial activities of those compounds were also evaluated and the highly active compounds were selected for further determination of minimal inhibitory concentrations (MICs). Compound 19 (MIC = 2 mu g/mL) was found to be highly active against the gram-negative bacteria Escherichia coli (KCTC-1924) than the Ampicillin standard (MIC = 4 mu g/mL). Compound 22 (MIC = 0.5 mu g/mL) inhibited gram-positive bacteria Staphylococcus aureus (KCTC-1916) growth as effectively as ampicillin (MIC = 0.5 mu g/mL).

  DOI：

  10.1007/s00044-014-0929-9

文献信息

• A novel and efficient synthesis of diverse dihydronaphtho[1,2-b]furans using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones to olefins and its application to furomollugin
  作者：Likai Xia、Yong Rok Lee

  DOI：10.1039/c3ob40977e

  日期：——

  A novel approach was developed for the synthesis of diverse dihydronaphtho[1,2-b]furans from 1,4-naphthoquinones and olefins in the presence of ceric ammonium nitrate. This reaction provides a rapid route for the synthesis of a variety of dihydronaphtho[1,2-b]furans and naphtho[1,2-b]furans bearing different substituents. This methodology was also used to synthesize the biologically important natural

  开发了一种新的方法，用于在硝酸铈铵的存在下，由1,4-萘醌和烯烃合成各种二氢萘[1,2- b ]呋喃。该反应为合成各种带有不同取代基的二氢萘并[1,2- b ]呋喃和萘并[1,2- b ]呋喃提供了一条快速途径。该方法也仅用两个步骤就可以合成生物学上重要的天然产物呋喃洛金。
• KR2015/64952
  申请人：——

  公开号：——

  公开（公告）日：——
• Investigation towards an efficient synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones
  作者：Blaise Mavinga Mbala、Jan Jacobs、Pieter Claes、Virima Mudogo、Norbert De Kimpe

  DOI：10.1016/j.tet.2011.09.021

  日期：2011.11

  As part of our research on 2-aza analogues of pentalongin, the active principle of Pentas longiflora Oliv., the first synthesis of 2,3-disubstituted benzo[g]isoquinoline-1,5,10(2H)-triones via 3,4-disubstituted 6-hydroxybenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-diones as the key intermediates is reported. The latter compounds have been prepared by treating 2-methoxycarbonyl-1,4-naphthoquinone with N-substituted enaminoesters under acidic conditions. These reagents are easily accessible from readily available 1,4-dihydroxy-2-naphthoic acid, beta-ketoesters and primary amines. Finally, a short synthesis of substituted benzo[g]isoquinoline-1,5,10(2H)-triones is achieved by an oxidative addition of N-substituted enaminoesters onto methyl 1,4-dihydroxynaphthalene-2-carboxylate. (C) 2011 Elsevier Ad. All rights reserved.
• Antioxidant and antibacterial evaluation of synthetic furomollugin and its diverse analogs
  作者：Likai Xia、Akber Idhayadhulla、Yong Rok Lee、Sung Hong Kim、Young-Jung Wee

  DOI：10.1007/s00044-014-0929-9

  日期：2014.7

  Diverse furomollugin (3) and its analogs (11-22) were synthesized in high yields via ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition as a key step. The in vitro antioxidant activities of synthesized compounds were determined by analyzing radical scavenging activities for 1,1-diphenyl-2-picrylhydrazyl (DPPH), nitric oxide, and hydrogen peroxide assays. The results showed that the synthesized furomollugin analogs had effective antioxidant power. Dihydronaphthofurans with 2-alkyoxy or 2-aryl group were the most potent radical scavengers in DPPH assay. Moreover, the antibacterial activities of those compounds were also evaluated and the highly active compounds were selected for further determination of minimal inhibitory concentrations (MICs). Compound 19 (MIC = 2 mu g/mL) was found to be highly active against the gram-negative bacteria Escherichia coli (KCTC-1924) than the Ampicillin standard (MIC = 4 mu g/mL). Compound 22 (MIC = 0.5 mu g/mL) inhibited gram-positive bacteria Staphylococcus aureus (KCTC-1916) growth as effectively as ampicillin (MIC = 0.5 mu g/mL).
• Construction of Functionalized <i>ortho</i>‐Naphthoquinone Methides via Site‐Selective Ring Opening of 1‐Siloxy‐1,4‐epoxy‐1,4‐dihydronaphthalenes
  作者：Takaaki Aijima、Shinsuke Komagawa、Shuji Akai、Yoshinari Sawama

  DOI：10.1002/adsc.202300968

  日期：2023.11.21

  underwent automatic site-selective ring opening because of the synergetic effect of the steric strain of the 1,4-epoxy moiety and the electron-donating ability of the siloxy group on the acetal structure to afford the precursors of ortho-naphthoquinone methides (o-NQMs). Subsequent Lewis acid-facilitated o-NQM formation and annulation with olefins afforded multi-fused heterocycles. Notably, the consecutive

  由苯炔和呋喃生成的1-甲硅烷氧基-4-(苄氧基)甲基-1,4-环氧-1,4-二氢萘由于1,4空间张力的协同作用而自动进行位点选择性开环-环氧部分和缩醛结构上甲硅烷氧基的给电子能力，提供邻萘醌甲基化物（o -NQMs）的前体。随后路易斯酸促进邻-NQM 形成并与烯烃成环，得到多稠合杂环。值得注意的是，rubioncolin B 的连续六环骨架是通过萘并呋喃衍生物的溶剂依赖性区域选择性成环构建的。