2-carbomethoxy-3-hexyloxy-hydroquinone | 203628-86-8

• 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: 2-carbomethoxy-3-hexyloxy-hydroquinone
• 英文别名: Methyl 2-hexoxy-3,6-dihydroxybenzoate
• CAS: 203628-86-8
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: FJYWIZSTGSURND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-carbomethoxy-3-hexyloxy-hydroquinone 在 溶剂黄146 作用下， 以 喹啉 为溶剂， 以70%的产率得到2-hexanyloxyhydroquinone
  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 在 sodium dithionite 、 magnesium chloride 作用下， 以 二氯甲烷 、 水 、 甲苯 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

文献信息

• Copper-catalysed oxidative alkoxylation of acyl- and carbomethoxy-hydroquinones
  作者：Patrice Capdevielle、Michel Maumy

  DOI：10.1016/s0040-4020(00)00947-9

  日期：2001.1

  Oxidation of title hydroquinones by an [O-2/(CuCl)-Cl-I] system in the presence of alcohols yields (71-88%) corresponding regioselectively 3-alkoxylated compounds. Compared with the classical procedure (silver oxide oxidation) in which alcohols have to be added to intermediate quinones in a second step, leading to a 1:1 mixture of starting material and final quinones, this new selective one-pot system does not oxidize alcohols and regenerates intermediate quinones from starting hydroquinones. Moreover, in situ trapping of the unstable formyl-quinone now allows the preparation of its 3-alkoxy derivative. (C) 2000 Elsevier Science Ltd. All rights reserved.