5-methoxy-2-(prop-1-en-2-yl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-methoxy-2-(prop-1-en-2-yl)phenol
• 英文别名: 2-Isopropenyl-5-methoxy-phenol；2-Oxy-4-methoxy-1-isopropenyl-benzol；5-methoxy-2-prop-1-en-2-ylphenol
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: DORPANARYYHSMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methoxy-2-(prop-1-en-2-yl)phenol 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 以43%的产率得到8-methoxy-4-methyl-1,2-diphenylspiro[4,5] deca-1,3,7,9-tetraen-6-one
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes

  摘要：

  Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.

  DOI：

  10.1021/ja5034952
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 5-methoxy-2-(prop-1-en-2-yl)phenol
  参考文献：
  名称：

  v. Pechmann; Cohen, Chemische Berichte, 1884, vol. 17, p. 2134

  摘要：

  DOI：

文献信息

• Palladium(II)-Catalyzed Annulation between <i>ortho</i>-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome
  作者：Noelia Casanova、Karina P. Del Rio、Rebeca García-Fandiño、José L. Mascareñas、Moisés Gulías

  DOI：10.1021/acscatal.6b00739

  日期：2016.5.6

  2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-like products through a pathway involving a β-hydrogen elimination step. Computational studies suggest that the square planar

  2-烯基酚与丙二烯反应，在催化量的 Pd(II) 和 Cu(II) 处理后，以高收率和非常好的区域和非对映选择性得到苯并氧杂环庚烷产品。这与使用 Rh 催化剂获得的结果形成对比，后者通过涉及 β-氢消除步骤的途径提供类色烯产物。计算研究表明，钯的方形平面几何形状对于促进形成 oxepine 产品所需的还原消除过程至关重要。
• Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes
  作者：Andrés Seoane、Noelia Casanova、Noelia Quiñones、José L. Mascareñas、Moisés Gulías

  DOI：10.1021/ja5034952

  日期：2014.5.28

  Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.
• v. Pechmann; Cohen, Chemische Berichte, 1884, vol. 17, p. 2134
  作者：v. Pechmann、Cohen

  DOI：——

  日期：——