1,4-二乙酰氧基-2,5-二甲基萘 | 253186-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,4-二乙酰氧基-2,5-二甲基萘
• 英文名称: 2,5-dimethylnaphthalene-1,4-diol diacetate
• 英文别名: 1,4-diacetoxy-2,5-dimethylnaphthalene；1,4-diacetoxy-2,5-dimethyl-naphthalene；1,4-Diacetoxy-2,5-dimethyl-naphthalin；(4-Acetyloxy-3,8-dimethylnaphthalen-1-yl) acetate
• CAS: 253186-23-1
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: VOFJVXDJLWIHJC-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  404.8±33.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-二乙酰氧基-2,5-二甲基萘 在 四氟硼酸-二乙醚络合物 、 环戊醇 、 Candida antarctica lipase B immobilized on acrylic resin 、 四丁基碘化铵 、 caesium carbonate 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 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：

  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
• 作为产物：
  描述：

  2,5-dimethylbenzoquininone 、 乙酸酐 在 sodium acetate 、 锌 作用下， 反应 0.25h， 以87%的产率得到1,4-二乙酰氧基-2,5-二甲基萘
  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

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.