3-(2-(1-methoxyprop-2-yn-1-yl)cyclohex-1-en-1-yl)thiophene | 1393739-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(2-(1-methoxyprop-2-yn-1-yl)cyclohex-1-en-1-yl)thiophene
• 英文别名: 3-[2-(1-Methoxyprop-2-ynyl)cyclohexen-1-yl]thiophene；3-[2-(1-methoxyprop-2-ynyl)cyclohexen-1-yl]thiophene
• CAS: 1393739-93-9
• 化学式: C₁₄H₁₆OS
• 分子量: 232.346
• InChiKey: YDTFPVAZBJGNQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-(1-methoxyprop-2-yn-1-yl)cyclohex-1-en-1-yl)thiophene 在 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 16.0h， 以99%的产率得到5-methoxy-4-methyl-6,7,8,9-tetrahydronaphtho[2,1-b]thiophene
  参考文献：
  名称：

  Cycloaromatization Protocol for Synthesis of Polysubstituted Phenol Derivatives: Method Development and Mechanistic Studies

  摘要：

  The scope of the cycloaromatization of propargylic ethers was explored using operationally simple air- and moisture-insensitive conditions. Highly substituted phenol derivatives were obtained in high yields. Mechanistic experiments indicate that the reaction occurs by an electro-cyclization followed by 1,3-proton transfer.

  DOI：

  10.1021/jo3010952
• 作为产物：
  描述：

  2-溴-1-环己烯-1-甲醛 在 四(三苯基膦)钯 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 48.78h， 生成 3-(2-(1-methoxyprop-2-yn-1-yl)cyclohex-1-en-1-yl)thiophene
  参考文献：
  名称：

  Cycloaromatization Protocol for Synthesis of Polysubstituted Phenol Derivatives: Method Development and Mechanistic Studies

  摘要：

  The scope of the cycloaromatization of propargylic ethers was explored using operationally simple air- and moisture-insensitive conditions. Highly substituted phenol derivatives were obtained in high yields. Mechanistic experiments indicate that the reaction occurs by an electro-cyclization followed by 1,3-proton transfer.

  DOI：

  10.1021/jo3010952

文献信息

• Cycloaromatization Protocol for Synthesis of Polysubstituted Phenol Derivatives: Method Development and Mechanistic Studies
  作者：William T. Spencer、Alison J. Frontier

  DOI：10.1021/jo3010952

  日期：2012.9.7

  The scope of the cycloaromatization of propargylic ethers was explored using operationally simple air- and moisture-insensitive conditions. Highly substituted phenol derivatives were obtained in high yields. Mechanistic experiments indicate that the reaction occurs by an electro-cyclization followed by 1,3-proton transfer.