methyl 2-butoxy-5-hydroxy-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate | 1452153-38-6

• 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: methyl 2-butoxy-5-hydroxy-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate
• 英文别名: Methyl 2-butoxy-5-hydroxy-2,3-dihydrobenzo[g][1]benzofuran-4-carboxylate；methyl 2-butoxy-5-hydroxy-2,3-dihydrobenzo[g][1]benzofuran-4-carboxylate
• CAS: 1452153-38-6
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: LLOMYBKJGDCFOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-butoxy-5-hydroxy-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以86%的产率得到呋喃大叶茜草素; 5-羟基萘并[1,2-b]呋喃-4-甲酸甲酯
  参考文献：
  名称：

  A Four-Step Total Synthesis of Radermachol

  摘要：

  Radermachol has been synthesized in four steps and an overall yield of 22% via key ytterbium triflate catalyzed furannulation and intramolecular nucleophilic acylation reactions.

  DOI：

  10.1021/ol500862w
• 作为产物：
  描述：

  1-羟基-4-甲氧基-2-萘甲酸甲酯 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 methyl 2-butoxy-5-hydroxy-2,3-dihydronaphtho[1,2-b]furan-4-carboxylate
  参考文献：
  名称：

  A Four-Step Total Synthesis of Radermachol

  摘要：

  Radermachol has been synthesized in four steps and an overall yield of 22% via key ytterbium triflate catalyzed furannulation and intramolecular nucleophilic acylation reactions.

  DOI：

  10.1021/ol500862w

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：——
• 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).
• A Four-Step Total Synthesis of Radermachol
  作者：Marco Buccini、Matthew J. Piggott

  DOI：10.1021/ol500862w

  日期：2014.5.2

  Radermachol has been synthesized in four steps and an overall yield of 22% via key ytterbium triflate catalyzed furannulation and intramolecular nucleophilic acylation reactions.