1,2,3,4,5-Pentadeuterio-6-[2-(1-methoxyprop-2-ynyl)cyclohexen-1-yl]benzene | 1393739-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,3,4,5-Pentadeuterio-6-[2-(1-methoxyprop-2-ynyl)cyclohexen-1-yl]benzene
• 英文别名: 1,2,3,4,5-pentadeuterio-6-[2-(1-methoxyprop-2-ynyl)cyclohexen-1-yl]benzene
• CAS: 1393739-98-4
• 化学式: C₁₆H₁₈O
• 分子量: 231.279
• InChiKey: VQGCKGDVYQIZDC-NPMXJOAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4,5-Pentadeuterio-6-[2-(1-methoxyprop-2-ynyl)cyclohexen-1-yl]benzene 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， 生成 5,6,7,8-Tetradeuterio-10-methoxy-9-methyl-1,2,3,4-tetrahydrophenanthrene 、 5,6,7,8-Tetradeuterio-9-(deuteriomethyl)-10-methoxy-1,2,3,4-tetrahydrophenanthrene
  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 1,2,3,4,5-Pentadeuterio-6-[2-(1-methoxyprop-2-ynyl)cyclohexen-1-yl]benzene
  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.