Methyl 2-hexoxy-3,6-dioxocyclohexa-1,4-diene-1-carboxylate | 203628-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2-hexoxy-3,6-dioxocyclohexa-1,4-diene-1-carboxylate
• CAS: 203628-80-2
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: OFTFNPAQKIJDHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-hexoxy-3,6-dioxocyclohexa-1,4-diene-1-carboxylate 在 sodium dithionite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 生成 2-carbomethoxy-3-hexyloxy-hydroquinone
  参考文献：
  名称：

  Experimental studies of lewis acid catalyzed additions of long chained alcohols to activated 1,4-benzoquinone

  摘要：

  Lewis acid promoted additions of long chained alcohols to 2-carbomethoxy-1,4-benzoquinone (1) have been examined by using various LAs; AlCl3, TiCl4, MgBr2 and MgCl2. It has been found that the bidentate Lewis acid MgCl2, having ability to coordinate to both carbonyl oxygens (chelate control) of 2-carbomethoxy-1,4-benzoquinone (1), produced the addition product almost quantitatively at mild conditions. The MgCl2 catalyzed additions of alcohols have been utilized in the synthesis of rare 2-alkoxyhydroquinones (7a-e). The reactions between quinone 1, alcohol and AlCl3 or TiCl4 have also been investigated by using NMR spectroscopy. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10409-4
• 作为产物：
  描述：

  methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate 、 正己醇 在 magnesium chloride 作用下， 以 甲苯 为溶剂， 以80%的产率得到Methyl 2-hexoxy-3,6-dioxocyclohexa-1,4-diene-1-carboxylate
  参考文献：
  名称：

  Experimental studies of lewis acid catalyzed additions of long chained alcohols to activated 1,4-benzoquinone

  摘要：

  Lewis acid promoted additions of long chained alcohols to 2-carbomethoxy-1,4-benzoquinone (1) have been examined by using various LAs; AlCl3, TiCl4, MgBr2 and MgCl2. It has been found that the bidentate Lewis acid MgCl2, having ability to coordinate to both carbonyl oxygens (chelate control) of 2-carbomethoxy-1,4-benzoquinone (1), produced the addition product almost quantitatively at mild conditions. The MgCl2 catalyzed additions of alcohols have been utilized in the synthesis of rare 2-alkoxyhydroquinones (7a-e). The reactions between quinone 1, alcohol and AlCl3 or TiCl4 have also been investigated by using NMR spectroscopy. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10409-4

文献信息

• Experimental studies of lewis acid catalyzed additions of long chained alcohols to activated 1,4-benzoquinone
  作者：Osmo E.O. Hormi、Anu M. Moilanen

  DOI：10.1016/s0040-4020(97)10409-4

  日期：1998.2

  Lewis acid promoted additions of long chained alcohols to 2-carbomethoxy-1,4-benzoquinone (1) have been examined by using various LAs; AlCl3, TiCl4, MgBr2 and MgCl2. It has been found that the bidentate Lewis acid MgCl2, having ability to coordinate to both carbonyl oxygens (chelate control) of 2-carbomethoxy-1,4-benzoquinone (1), produced the addition product almost quantitatively at mild conditions. The MgCl2 catalyzed additions of alcohols have been utilized in the synthesis of rare 2-alkoxyhydroquinones (7a-e). The reactions between quinone 1, alcohol and AlCl3 or TiCl4 have also been investigated by using NMR spectroscopy. (C) 1998 Elsevier Science Ltd. All rights reserved.