1-acetoxy-2,5-dimethyl-4-hydroxynaphthalene | 253186-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-acetoxy-2,5-dimethyl-4-hydroxynaphthalene
• 英文别名: (4-Hydroxy-2,5-dimethylnaphthalen-1-yl) acetate
• CAS: 253186-24-2
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: DMSFNJNRUBHREU-UHFFFAOYSA-N

物化性质

• 熔点：
  184-185 °C
• 沸点：
  400.3±33.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetoxy-2,5-dimethyl-4-hydroxynaphthalene 在 四氟硼酸-二乙醚络合物 、 sodium hydroxide 、 selenium(IV) oxide 、 sodium dithionite 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 丙酮 为溶剂， 反应 54.03h， 生成 3,6,9-三甲基萘并[1,8-bc]吡喃-7,8-二酮
  参考文献：
  名称：

  Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate

  摘要：

  The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations.

  DOI：

  10.1021/np990277g
• 作为产物：
  描述：

  甲基苯醌 在 环戊醇 、 氯化锑(V) 作用下， 反应 19.5h， 生成 1-acetoxy-2,5-dimethyl-4-hydroxynaphthalene
  参考文献：
  名称：

  Lipase-Catalyzed Site-Selective Deacetylation of Sterically Hindered Naphthohydroquinone Diacetate and Its Application to the Synthesis of a Heterocyclic Natural Product

  摘要：

  DOI：

  10.3987/com-18-s(f)12

文献信息

• Lipase-Catalyzed Site-Selective Deacetylation of Sterically Hindered Naphthohydroquinone Diacetate and Its Application to the Synthesis of a Heterocyclic Natural Product
  作者：Takeshi Sugai、Riichi Hashimoto、Ayaka Sakakura、Kengo Hanaya、Shuhei Higashibayashi

  DOI：10.3987/com-18-s(f)12

  日期：——
• Synthesis of Mansonone F Based on the Regioselective Hydrolysis of a Hydroquinone Diacetate
  作者：Ruth L. Nunes、Lothar W. Bieber、Ricardo L. Longo

  DOI：10.1021/np990277g

  日期：1999.12.1

  The synthesis of mansonone F (1), an antimicrobial sesquiterpenequinone, is described. Starting from 2,5-dimethyl-1,4-naphthoquinone (5), the corresponding selectively protected hydroquinone 9 was prepared in four steps. Alkylation of 9 using chloroacetone, cyclization, and oxidation to the o-quinone completed the reaction sequence in 7.5% overall yield. The regioselectivity for the basic hydrolysis of hydroquinone diacetate 6 was discussed on the basis of MO calculations.