4-(6-Ethenyl-1,3-benzodioxol-5-yl)phenol | 130537-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(6-Ethenyl-1,3-benzodioxol-5-yl)phenol
• CAS: 130537-98-3
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: LPIYHOASWGXHHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-(6-Ethenyl-1,3-benzodioxol-5-yl)phenol 在 碘苯二乙酸 作用下， 以34%的产率得到5-Methoxyspiro[5,6-dihydrocyclopenta[f][1,3]benzodioxole-7,4'-cyclohexa-2,5-diene]-1'-one
  参考文献：
  名称：

  通过2'-烯基-对-苯基苯酚与碘代苯二乙酸酯的氧化来螺旋环化的2,5-环己二酮

  摘要：

  经由碘代苯二乙酸酯对2'-烯基取代的对苯基苯酚的氧化得到螺环化的2,5-环己二酮。

  DOI：

  10.1016/s0040-4039(00)97673-1

文献信息

• Spiro-annulated 2,5-cyclohexadienones via oxidation of 2′-alkenyl-p-phenyl phenols with iodobenzene diacetate
  作者：Andrew Callinan、Ying Chen、Gary W. Morrow、John S. Swenton

  DOI：10.1016/s0040-4039(00)97673-1

  日期：1990.1

  The oxidation of 2′-alkenyl-substituted p-phenyl phenols via iodobenzene diacetate gives spiro-annulated-2,5-cyclohexadienones.

  经由碘代苯二乙酸酯对2'-烯基取代的对苯基苯酚的氧化得到螺环化的2,5-环己二酮。
• CALLINAN, ANDREW;YING, CHEN;MORROW, GARY W.;SWENTON, JOHN S., TETRAHEDRON LETT., 31,(1990) N2, C. 4551-4552
  作者：CALLINAN, ANDREW、YING, CHEN、MORROW, GARY W.、SWENTON, JOHN S.

  DOI：——

  日期：——
• 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.