phenethyl 1,4-dihydroxy-2-naphthoate | 1558797-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: phenethyl 1,4-dihydroxy-2-naphthoate
• 英文别名: 2-Phenylethyl 1,4-dihydroxynaphthalene-2-carboxylate
• CAS: 1558797-71-9
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: IXWWZFROOVNKKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  phenethyl 1,4-dihydroxy-2-naphthoate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 苯硼酸 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 13.0h， 生成 phenethyl 6-hydroxy-2-methyl-2-(4-methylpentyl)-3,4-dihydro-2H-benzo[h]chromene-5-carboxylate
  参考文献：
  名称：

  Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities

  摘要：

  Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)(2)/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 mu M) compared with BHT (IC50 = 9.67 mu M). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 mu g/mL. Structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR data and high-resolution mass spectrometry. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.008
• 作为产物：
  描述：

  1,4-二羟基-2-萘甲酸 、 乙基溴苯 在 盐酸 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以75%的产率得到phenethyl 1,4-dihydroxy-2-naphthoate
  参考文献：
  名称：

  Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities

  摘要：

  Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)(2)/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 mu M) compared with BHT (IC50 = 9.67 mu M). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 mu g/mL. Structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR data and high-resolution mass spectrometry. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.008

文献信息

• Synthesis of functionalized 3-aryl-3<i>H</i>-benzofuranone derivatives from aryl acetate <i>via</i> [3 + 2] annulation of 1,4-dihydroxy-2-naphthoic acid ester
  作者：Huan Wang、Yuxiang Zhou、Ying Xie、Yi Liu、Yulong Li、Hao Zhang、Jilang Long

  DOI：10.1039/d2ob02319a

  日期：——

  A novel [3 + 2] cascade reaction of aryl acetate with 1,4-dihydroxy-2-naphthoic acid ester by cooperative catalysis of isothiourea and vanadium is developed. The key step of the reaction is that the C1-ammonium enolates generated from aryl acetate will cycloadduct to 1,4-naphthoquinone intermediates. 3-Aryl-3H-benzofuranone derivatives can be prepared in medium to good yields under mild conditions

  通过异硫脲和钒的协同催化，开发了乙酸芳基酯与 1,4-二羟基-2-萘甲酸酯的新型 [3 + 2] 级联反应。该反应的关键步骤是乙酸芳基酯生成的C1-烯醇化铵环加成1,4-萘醌中间体。3-Aryl-3H - benzofuranone 衍生物可以在温和条件下以中等到良好的产率制备。
• KR101612996
  申请人：——

  公开号：——

  公开（公告）日：——