2-phenyl-4,4,6,6-tetradeuterio-5-ethyl-1,3-dioxane | 185246-56-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-phenyl-4,4,6,6-tetradeuterio-5-ethyl-1,3-dioxane
• 英文别名: 4,4,6,6-Tetradeuterio-5-ethyl-2-phenyl-1,3-dioxane
• CAS: 185246-56-4
• 化学式: C₁₂H₁₆O₂
• 分子量: 196.226
• InChiKey: FSKJESVNEFUDMR-LZMSFWOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-4,4,6,6-tetradeuterio-5-ethyl-1,3-dioxane 、 苯 在 三氟甲磺酸 作用下， 生成 deuterio-diphenyl-methane
  参考文献：
  名称：

  Superacid-Catalyzed Reductive Friedel−Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals

  摘要：

  Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethanesulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph(2)CHOCH(2)CH(2)CH(2)OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.

  DOI：

  10.1021/jo961897e
• 作为产物：
  描述：

  乙基丙二酸二乙酯 在 lithium aluminium deuteride 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 2-phenyl-4,4,6,6-tetradeuterio-5-ethyl-1,3-dioxane
  参考文献：
  名称：

  Superacid-Catalyzed Reductive Friedel−Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals

  摘要：

  Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethanesulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph(2)CHOCH(2)CH(2)CH(2)OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.

  DOI：

  10.1021/jo961897e

文献信息

• Superacid-Catalyzed Reductive Friedel−Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals
  作者：Shin-ichi Fukuzawa、Teruhisa Tsuchimoto、Tamejiro Hiyama

  DOI：10.1021/jo961897e

  日期：1997.1.1

  Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethanesulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph(2)CHOCH(2)CH(2)CH(2)OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.