5,8-dimethoxytetralone methyl enol ether | 235792-71-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,8-dimethoxytetralone methyl enol ether
• 英文别名: 4,5,8-Trimethoxy-1,2-dihydronaphthalene
• CAS: 235792-71-9
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: BDVJJNNTIZPGPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxytetralone methyl enol ether 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 43.5h， 生成 5,8-dimethoxyspiro[2,3-dihydro-1H-naphthalene-4,3'-2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene]-8'-ol
  参考文献：
  名称：

  Total Syntheses of (±)-Preussomerins G and I

  摘要：

  Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.

  DOI：

  10.1021/ol990020+
• 作为产物：
  描述：

  5,8-二甲氧基-1-四氢萘酮 、 原甲酸三甲酯 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 39.0h， 以94%的产率得到5,8-dimethoxytetralone methyl enol ether
  参考文献：
  名称：

  Total Syntheses of (±)-Preussomerins G and I

  摘要：

  Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.

  DOI：

  10.1021/ol990020+

文献信息

• Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues
  作者：Ruina Wang、Guoyue Liu、Mingyan Yang、Mingan Wang、Ligang Zhou

  DOI：10.3390/molecules21050600

  日期：——

  Total synthesis of naturally occurring spirobisnaphthalene palmarumycin CP17 and its methoxy analogues was first achieved through Friedel-Crafts acylation, Wolff-Kishner reduction, intramolecular cyclization, ketalization, benzylic oxidation, and demethylation using the inexpensive and readily available methoxybenzene, 1,2-dimethoxybenzene and 1,4-dimethoxybenzene and 1,8-dihydroxynaphthalene as raw

  天然存在的螺双萘帕玛霉素 CP17 及其甲氧基类似物的全合成首先通过 Friedel-Crafts 酰化、Wolff-Kishner 还原、分子内环化、缩酮化、苄基氧化和脱甲基化实现，使用廉价且容易获得的甲氧基苯、1,2-二甲氧基苯和以1,4-二甲氧基苯和1,8-二羟基萘为原料。在环境温度下用 (CH3)3SiI 去甲基化导致环 A 芳构化和缩醛裂解，产生联萘醚。评估了这些螺二萘衍生物的抗真菌活性，结果表明 5 和 9b 对 P. piricola 的 EC50 值分别为 9.34 µg/mL 和 12.35 µg/mL。