3-Methoxy-5-(2-methyl-1,3-dioxolan-2-yl)cyclohexa-3,5-diene-1,2-dione | 926906-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methoxy-5-(2-methyl-1,3-dioxolan-2-yl)cyclohexa-3,5-diene-1,2-dione
• CAS: 926906-98-1
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: PKEXNKMFBJPMSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Methoxy-5-(2-methyl-1,3-dioxolan-2-yl)cyclohexa-3,5-diene-1,2-dione 在 sodium hydroxide 、 碘 、 N,N-二异丙基乙胺 、 乙酰氯 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 水 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Total synthesis of (±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane

  摘要：

  Regioselective cycloaddition of o-quinone 4 and protected sinapyl alcohol 2 gave 1,4-benzodioxane 5, which was converted to (+/-)-nitidanin (6), an antimalarial compound. Two novel procedures were developed to determine the location of the side chains of the adduct (5) based on partial ring cleavage. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.170
• 作为产物：
  描述：

  丁香醛 在 咪唑 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四丁基氟化铵 、 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.0h， 生成 3-Methoxy-5-(2-methyl-1,3-dioxolan-2-yl)cyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  Total synthesis of (±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane

  摘要：

  Regioselective cycloaddition of o-quinone 4 and protected sinapyl alcohol 2 gave 1,4-benzodioxane 5, which was converted to (+/-)-nitidanin (6), an antimalarial compound. Two novel procedures were developed to determine the location of the side chains of the adduct (5) based on partial ring cleavage. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.170

文献信息

• Inverse electron demand hetero-Diels–Alder reaction in preparing 1,4-benzodioxin from o-quinone and enamine
  作者：Jinsong Zhang、Chris Taylor、Erich Bowman、Leo Savage-Low、Michael W. Lodewyk、Larry Hanne、Guang Wu

  DOI：10.1016/j.tetlet.2013.09.013

  日期：2013.11

  A process for synthesizing 1,4-benzodioxin, through oxidation of a phenol to an o-quinone followed by treatment with an enamine, has been developed. Adduct stereochemistry is found to be retained via this one-pot reaction. The method uses hypervalent iodine reagent under mild conditions and is compatible with a wide scope of phenols and enamines. Published by Elsevier Ltd.
• Total synthesis of cleomiscosin C via a regioselective cycloaddition reaction of o-quinone
  作者：Atsuhito Kuboki、Chie Maeda、Tetsuya Arishige、Kohei Kuyama、Mami Hamabata、Susumu Ohira

  DOI：10.1016/j.tetlet.2008.05.051

  日期：2008.7

  We have achieved total synthesis of cleomiscosin C (aquillochin) through regioselective cycloaddition of o-quinone and protected sinapyl alcohol as a key step. During preparation of o-quinone from phenol by IBX oxidation, silyl substituents adjacent to the phenolic hydroxyl group afforded effective inhibition of an undesired oxidative elimination. (c) 2008 Elsevier Ltd. All rights reserved.