2-(2',5'-dimethoxyphenyl)-1,3-dioxolane | 72054-76-3

• 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-(2',5'-dimethoxyphenyl)-1,3-dioxolane
• 英文别名: 1,3-Dioxolane, 2-(2,5-dimethoxyphenyl)-；2-(2,5-dimethoxyphenyl)-1,3-dioxolane
• CAS: 72054-76-3
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: RREVKHLNNDJPDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2',5'-dimethoxyphenyl)-1,3-dioxolane 在 三甲基溴硅烷 、 碘苯二乙酸 作用下， 以38%的产率得到4-溴-2,5-二甲氧基苯甲醛
  参考文献：
  名称：

  Hypervalent Iodine Chemistry:  Mechanistic Investigation of the Novel Haloacetoxylation, Halogenation, and Acetoxylation Reactions of 1,4-Dimethoxynaphthalenes

  摘要：

  Treatment of 1,4-dimethoxynaphthalenes with iodosobenzene diacetate and trimethylsilyl chloride or bromide furnished the haloacetoxylated, acetoxylated, and halogenated 1,4-dimethoxynaphthalenes in excellent yield. The reaction pathway for each transformation was shown to be a function of reagent stoichiometry. A mechanistic hypothesis is presented that rationalizes the reaction pathways and explains the subtle differences in the halogenation reactions. The acetoxylation, for example, is thought to involve the formation of an iodonium ion that promotes the nucleophilic addition of acetate ion and subsequent 1,2-acetyl migration. Bromination occurs as a direct result of the oxidation of trimethylsilyl bromide to bromine, followed by electrophilic aromatic substitution. Chlorination is thought to proceed via a radical process and not the formation of molecular chlorine from the dissociation of iodosobenzene dichloride. The haloacetoxylation reaction also appears to be fairly specific for 1,4-dimethoxynaphthalenes, since the analogous reaction with a 1,4-dimethoxybenzene derivative was unsuccessful.

  DOI：

  10.1021/jo970525i
• 作为产物：
  描述：

  乙二醇 、 2,5-二甲氧基苯甲醛 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以83%的产率得到2-(2',5'-dimethoxyphenyl)-1,3-dioxolane
  参考文献：
  名称：

  An Efficient, Simple and Inexpensive Method for the Preparation of 1,4-Benzoquinone MonoketalsviaAnodic Oxidation of 1,4-Dimethoxybenzenes

  摘要：

  Anodic oxidation of a series of 1-substituted-2,5-dimethoxybenzenes gives 2-substituted-1,1,4,4-tetramethoxycyclohexa-2,5-dienes in almost quantitative crude yield. Selective monohydrolysis of these bis-ketals is possible in many cases, and gives 3-substituted-4,4-dimethoxycyclohexa-2,5-dienones in good to excellent overall yield.

  DOI：

  10.1080/00397919408010619

文献信息

• Anodic oxidation of 1,4-dimethoxy aromatic compounds. A facile route to functionalized quinone bisketals
  作者：Daniel R. Henton、Richard A. McCreery、John S. Swenton

  DOI：10.1021/jo01291a001

  日期：1980.2
• Efficient Method for Synthesis of Angucyclinone Antibiotics via Gold-Catalyzed Intramolecular [4 + 2] Benzannulation:  Enantioselective Total Synthesis of (+)-Ochromycinone and (+)-Rubiginone B₂
  作者：Kenichiro Sato、Naoki Asao、Yoshinori Yamamoto

  DOI：10.1021/jo051444m

  日期：2005.10.1

  An efficient synthetic approach to angucyclinone antibiotics, (+)-ochromycinone and (+)-rubiginone B-2, is reported. The key step involves the facile formation of 2,3-dihydrophenantren-4(1H)-one skeleton, an important framework of angucyclinone natural products, by using gold-catalyzed intramolecular [4 + 2] benzannulation reaction.
• HENTON D. R.; CHENARD B. L.; SWENTON J. S., J. CHEM. SOC. CHEM. COMMUN., 1979, NO 7, 326-327
  作者：HENTON D. R.、 CHENARD B. L.、 SWENTON J. S.

  DOI：——

  日期：——
• HENTON D. R.; MCCREERY R. L.; SWENTON J. S., J. ORG. CHEM., 1980, 45, NO 3, 369-378
  作者：HENTON D. R.、 MCCREERY R. L.、 SWENTON J. S.

  DOI：——

  日期：——
• Gautier Elisabeth C. L., Lewis Norman J., McKillop Alexander, Taylor Rich+, Synth. Commun, 24 (1994) N 20, S 2989-3008
  作者：Gautier Elisabeth C. L., Lewis Norman J., McKillop Alexander, Taylor Rich+

  DOI：——

  日期：——