1-(2-oxopropoxy)-4-benzyloxy-2,5-dimethylnaphthalene | 253186-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-oxopropoxy)-4-benzyloxy-2,5-dimethylnaphthalene
• 英文别名: 1-(2,5-Dimethyl-4-phenylmethoxynaphthalen-1-yl)oxypropan-2-one
• CAS: 253186-27-5
• 化学式: C₂₂H₂₂O₃
• 分子量: 334.415
• InChiKey: JJHNLSCEUUHDFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-oxopropoxy)-4-benzyloxy-2,5-dimethylnaphthalene 在 四氟硼酸-二乙醚络合物 、 selenium(IV) oxide 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.03h， 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：

  1-acetoxy-2,5-dimethyl-4-hydroxynaphthalene 在 sodium hydroxide 、 sodium dithionite 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 42.0h， 生成 1-(2-oxopropoxy)-4-benzyloxy-2,5-dimethylnaphthalene
  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