bis(3,4-dimethoxybenzyl) sulfoxide | 215384-53-5

• 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: bis(3,4-dimethoxybenzyl) sulfoxide
• 英文别名: 4-[(3,4-Dimethoxyphenyl)methylsulfinylmethyl]-1,2-dimethoxybenzene
• CAS: 215384-53-5
• 化学式: C₁₈H₂₂O₅S
• 分子量: 350.436
• InChiKey: BQANSGMJCUJZKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(3,4-dimethoxybenzyl) sulfoxide 在 manganese(IV) oxide 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,9,10-tetramethoxy-5,7-dihydrodibenzo[c,e]thiepine 6-oxide
  参考文献：
  名称：

  An economical and environmentally friendly oxidative biaryl coupling promoted by activated MnO₂

  摘要：

  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MnO2和BF3·OEt2的组合具有吸引力。

  DOI：

  10.1039/c4ob01409j
• 作为产物：
  描述：

  3,4-二甲氧基苄醇 在 sodium sulfide 、 双氧水 作用下， 生成 bis(3,4-dimethoxybenzyl) sulfoxide
  参考文献：
  名称：

  p-Hydroxy-Benzyl Ethers As Lignin Models. II

  摘要：

  DOI：

  10.1246/bcsj.27.53

文献信息

• 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).