3-methoxy-9-methylphenanthren-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-methoxy-9-methylphenanthren-2-ol
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: BVHMROIJWIGKBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-5-羟基-4-甲氧基苯甲醛 在 咪唑 、 iron(III) chloride 、 四(三苯基膦)钯 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 17.83h， 生成 3-methoxy-9-methylphenanthren-2-ol
  参考文献：
  名称：

  通过铁 (III) 催化的羰基-烯烃复分解反应制备多环芳烃

  摘要：

  多环芳烃是有机化学、药物化学和材料科学中的重要结构基序。基于铁(III)催化的羰基-烯烃复分解反应的设计原理描述了这些化合物的新合成策略的开发。该方法的特点是操作简单、官能团兼容性高和区域选择性，同时依赖 FeCl3 作为环境友好、地球丰富的金属催化剂。已经获得了氧杂环丁烷作为催化羰基-烯烃闭环复分解反应中间体的实验证据。

  DOI：

  10.1021/jacs.7b01114

文献信息

• Intramolecular Anodic Carbon−Carbon Bond Formation from Oxidized Phenol Intermediates. Effect of Oxygenated Substituents on the Yields of Spiro Dienones in Electrochemical and Iodobenzene Diacetate Oxidations
  作者：John S. Swenton、Andrew Callinan、Ying Chen、Jeffrey J. Rohde、Michael L. Kerns、Gary W. Morrow

  DOI：10.1021/jo951799d

  日期：1996.1.1

  The single-cell, constant-current anodic oxidation of a series of 4-(2-alkenylaryl)phenols was studied in which the aryl substituents were 2-vinyl-4,5-dimethoxy, 6a; 2-propenyl-4,5-dimethoxy, 9a; 2-vinyl-4,5-methylenedioxy, 6b; 2-propenyl-4,5-methylenedioxy, 9b; 2-vinyl-4-methoxy, 6c; 2-propenyl-4-methoxy, 9c; 2-vinyl-5-methoxy, 6d; and 2-propenyl-5-methoxy, 9d. Two compounds having methoxyl groups on the phenolic ring were also studied: 4-(2'-propenylphenyl)-2-methoxyphenol, 9e, and 4-(2'-propenylphenyl)-3-methoxyphenol, 9f. A novel synthetic route to the methoxy compounds 6c, 9c, 6d, and 9d was developed. This involved as a key step the MAD, bis(2,6-ditert-butyl-4-methylphenoxide)methylaluminum, mediated addition of organolithium and Grignard reagents to functionalize quinol ether derivatives. Anodic oxidation of compounds 6a, 9a, 9b, 6c, 9c, and 9d gave good yields of spiro dienones arising from trapping of the phenoxonium ion by the alkenyl side chain followed by reaction of the resulting cation with methanol. The products from the electrochemical oxidation of these 4-(2'-alkenylaryl)phenols were compared with those obtained from the iodobenzene diacetate oxidations. In general, the compounds that gave good yields of spiro dienones from electrochemical oxidation gave good yields from iodobenzene diacetate oxidations. However, there were two cases in which the results of the two oxidations did not parallel each other. Whereas anodic oxidation of 9f gave a low yield of spiro dienone, the iodobenzene diacetate route gave a 74% yield of this product. In the case of 9d, the opposite effect was noted: the electrochemical route gave a higher yield than did the iodobenzene diacetate oxidation.