2-Butyl-5-methoxy-1,4-naphthochinon | 92920-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Butyl-5-methoxy-1,4-naphthochinon
• 英文别名: 2-n-Butyl-5-methoxy-1,4-naphthalenedione；2-butyl-5-methoxy-1,4-naphthoquinone；2-Butyl-5-methoxynaphthalene-1,4-dione
• CAS: 92920-84-8
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: KQYWBEFDIBTRIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Butyl-5-methoxy-1,4-naphthochinon 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-Butyl-5-hydroxy-1,4-naphthoquinone
  参考文献：
  名称：

  Wurm; Baumann; Geres, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 6, p. 652 - 658

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基-1-萘酚 在 四丁基硫酸氢铵 sodium tetrahydroborate 、 potassium nitrososulfonate 、 氯甲酸乙酯 、 sodium carbonate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 水 、 丙酮 、 苯 为溶剂， 反应 7.5h， 生成 2-Butyl-5-methoxy-1,4-naphthochinon
  参考文献：
  名称：

  Wurm; Baumann; Geres, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 6, p. 652 - 658

  摘要：

  DOI：

文献信息

• Syntheses of Naphthoquinone Compounds Using Chromium Carbonyl Carbene Complexes
  作者：Masakazu Yamashita、Takahiro Ohishi

  DOI：10.1246/bcsj.66.1187

  日期：1993.4

  The chromium carbonyl carbene complexes bearing an acetoxyl group and a phenyl substituent were found to react smoothly with acetylene compounds to produce naphthoquinone derivatives in good yields after oxidation. This cycloaddition reaction proceeded regioselectively and several naphthoquinones were prepared selectively from the complex and unsymmetrical acetylenes.

  发现带有乙酰氧基和苯基取代基的铬羰基卡宾配合物可与乙炔化合物顺利反应，氧化后以良好的产率生成萘醌衍生物。这种环加成反应是区域选择性地进行的，并且从复杂的和不对称的乙炔中选择性地制备了几种萘醌。
• A strategy for generalization of the regiospecific synthesis of substituted quinones from cyclobutenediones
  作者：Lanny S. Liebeskind、Kenneth L. Granberg、Jing Zhang

  DOI：10.1021/jo00042a009

  日期：1992.7

  Documented within is a straightforward protocol for the synthesis of generally substituted benzoquinones and ring-fused quinones. Previously, the crucial issue of quinone substituent regiochemistry was resolved at the stage of addition of an unsaturated carbon nucleophile to a cyclobutenedione by using either symmetrically substituted cyclobutenediones or 3-alkoxy (or amino)-4-substituted-3-cyclobutenediones. In the former case there are no regioisomeric quinones formed, while in the latter, through resonance delocalization, the alkoxy (or amino) substituent renders one of the two carbonyl groups less reactive and directs the incoming nucleophile to the other. The placement of a wide variety of substituents about the quinone ring periphery has now been solved by the less restrictive strategy of sequential introduction of substituents onto a cyclobutenedione core. The chemistry commences with 3-isopropoxy-4-substituted-3-cyclobutene-1,2-diones. Addition of an aromatic, heteroaromatic, or alkenyl nucleophile to the more reactive carbonyl group provides 4-hydroxy-4-R(unsat)-2-cyclobutenones, which are protected as the methyl ethers by treatment with MeI/Ag2O/K2CO3 in MeCN. A second nucleophile is added, again in a 1,2-sense, providing highly substituted 3-isopropoxy-2-cyclobutenols that are arranged to cyclobutenones under acidic conditions. The resulting cyclobutenones are converted into substituted quinones by thermolysis at 140-degrees-C in o-xylene followed by oxidative workup with ceric ammonium nitrate. The substitution pattern about the quinone core is rigorously controlled by the sequence of introduction of the substituents.
• Wurm; Baumann; Geres, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 6, p. 652 - 658
  作者：Wurm、Baumann、Geres、Schmidt

  DOI：——

  日期：——