2,3,9,10-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepine | 65559-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 2,3,9,10-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepine
• 英文别名: 2,3,9,10-Tetramethoxy-5,7-dihydrobenzo[d][2]benzoxepine
• CAS: 65559-62-8
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: MLELSRNBFVYKNP-UHFFFAOYSA-N

物化性质

• 熔点：
  258 °C(Solv: benzene (71-43-2))
• 沸点：
  482.7±45.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,9,10-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepine 在 四氢呋喃 、 potassium dichromate 、 lithium aluminium tetrahydride 、 乙醇 、 三溴化磷 、 lithium hydride 、 溶剂黄146 、 丙酮 作用下， 生成 (4,5,4',5'-tetramethoxy-biphenyl-2,2'-diyl)-di-acetonitrile
  参考文献：
  名称：

  Matarasso-Tchiroukhine, Annales de Chimie (Cachan, France), 1958, vol. <13> 3, p. 405,425

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基甲苯 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 一氯化碘 、 铜 、 溶剂黄146 、 过氧化苯甲酰 作用下， 生成 2,3,9,10-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepine
  参考文献：
  名称：

  Cromartie et al., Journal of the Chemical Society, 1958, p. 1982,1984

  摘要：

  DOI：

文献信息

• An economical and environmentally friendly oxidative biaryl coupling promoted by activated MnO₂
  作者：Jingjing Yang、Shutao Sun、Ziyu Zeng、Hongbo Zheng、Wei Li、Hongxiang Lou、Lei Liu

  DOI：10.1039/c4ob01409j

  日期：——

  An activated manganese dioxide (MnO2)–BF3·OEt2 oxidation system was developed to efficiently mediate the intramolecular as well as intermolecular biaryl coupling. The oxidative coupling proceeds smoothly at ambient temperature to deliver the corresponding five- to eight-membered tricyclic products in good to excellent yields. The employment of the combination of MnO2 and BF3·OEt2 is attractive on the basis of economical and environmental issues.

  开发了一种活化的二氧化锰（MnO2）–BF3·OEt2氧化系统，能够高效地介导分子内和分子间的二芳基偶联。该氧化偶联在常温下顺利进行，产物为相应的五到八元环三环化合物，产率良好至优秀。基于经济和环境问题，使用 和 ·OEt2的组合具有吸引力。
• Thallium in organic synthesis. 59. Alkaloid synthesis via intramolecular nonphenolic oxidative coupling. Preparation of (.+-.)-ocoteine, (.+-.)-acetoxyocoxylonine, (.+-.)-3-methoxy-n-acetylnornantenine, (.+-.)-neolitsine, (.+-.)-kreysigine, (.+-.)-O-methylkreysigine, and (.+-.)-multifloramine
  作者：Edward C. Taylor、Juan G. Andrade、Gerhardus J. H. Rall、Alexander McKillop

  DOI：10.1021/ja00541a021

  日期：1980.10
• Seven- and eight-membered heterocyclic biaryl synthesis through a metal-free oxidative coupling reaction
  作者：Shutao Sun、Jingjing Yang、Fanmei Li、Zheng Lv、Wei Li、Hongxiang Lou、Lei Liu

  DOI：10.1016/j.tetlet.2014.10.103

  日期：2014.12

  A metal-free intramolecular biaryl coupling mediated by DDQ and BF3 center dot OEt2 was developed. The reaction proceeds smoothly at room temperature to give seven- and eight-membered heterocyclic biaryl compounds in up to 95% yields. Only 1 equiv of DDQ sufficed for the reaction, obviating the use of a large excess of oxidants and undesired chlorination pathway in metal-mediated process. (C) 2014 Elsevier Ltd. All rights reserved.
• Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent
  作者：Takeshi Takada、Mitsuhiro Arisawa、Michiyo Gyoten、Ryuji Hamada、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1021/jo980704f

  日期：1998.10.1

  The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a-e), N-benzyl-N-phenethylamines (2a-c) and N,N-dibenzylamines (3a-e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3. Et2O in CH2Cl2 to give the biaryl coupling products (4-6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12-15), whose side chain moiety could be easily cleaved by the known method to give 2,2'-substituted biphenyl compounds (16-18).