di-tert-butylbis(3,4-(methylenedioxy)phenoxy)silane | 215384-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: di-tert-butylbis(3,4-(methylenedioxy)phenoxy)silane
• 英文别名: Bis(1,3-benzodioxol-5-yloxy)-ditert-butylsilane
• CAS: 215384-51-3
• 化学式: C₂₂H₂₈O₆Si
• 分子量: 416.546
• InChiKey: DWVIRNXZCYFQJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  di-tert-butylbis(3,4-(methylenedioxy)phenoxy)silane 在 三氟化硼乙醚 、 四丁基氟化铵 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 4,5,4',5'-bis(methylenedioxy)biphenyl-2,2'-diol
  参考文献：
  名称：

  Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent

  摘要：

  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).

  DOI：

  10.1021/jo980704f
• 作为产物：
  描述：

  芝麻酚 、 二叔丁基硅基双(三氟甲烷磺酸) 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以78%的产率得到di-tert-butylbis(3,4-(methylenedioxy)phenoxy)silane
  参考文献：
  名称：

  Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent

  摘要：

  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).

  DOI：

  10.1021/jo980704f

文献信息

• A Novel and Useful Oxidative Intramolecular Coupling Reaction of Phenol Ether Derivatives on Treatment with a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid
  作者：Hiromi Hamamoto、Gopinathan Anilkumar、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1002/1521-3765(20021202)8:23<5377::aid-chem5377>3.0.co;2-h

  日期：2002.12.2

  The oxidative intramolecular coupling reaction of phenol ether derivatives (nonphenolic derivatives) on treatment with a novel combination of a hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) was studied. Biaryl compounds were obtained in excellent yields on treatment of highly substituted phenol ethers. On the other hand, spirodienones were specifically

  研究了酚醚衍生物（非酚类衍生物）在高价碘试剂，苯基碘双三氟乙酸酯（PIFA）和杂多酸（HPA）的新型组合下的氧化分子内偶联反应。通过处理高度取代的酚醚，可以以极好的收率获得联芳基化合物。另一方面，当优选的芳基偶联位点之一在对位被甲氧基取代时，特异形成螺二烯酮。
• A novel and efficient oxidative biaryl coupling reaction of phenol ether derivatives using a combination of hypervalent iodine(iii) reagent and heteropoly acid
  作者：Hiromi Hamamoto、Gopinathan Anilkumar、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1039/b111178g

  日期：2002.2.27

  A novel and efficient oxidative biaryl coupling reaction of phenol ether derivatives using a combination of hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), and heteropoly acid has been developed.

  已经开发了一种新型的高效苯酚醚衍生物的氧化联芳基偶合反应，该反应是结合使用高价碘（III）试剂，苯基碘（III）双（三氟乙酸酯）（PIFA）和杂多酸。
• 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).