3-methoxy-4,6-bis(1,1-diphenylmethyl)-1,2-benzoquinone | 212055-89-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-methoxy-4,6-bis(1,1-diphenylmethyl)-1,2-benzoquinone
• 英文别名: 3-Methoxy-4,6-bis(diphenylmethyl)-1,2-benzoquinone；3,5-Cyclohexadiene-1,2-dione, 4,6-bis(diphenylmethyl)-3-methoxy-；4,6-dibenzhydryl-3-methoxycyclohexa-3,5-diene-1,2-dione
• CAS: 212055-89-5
• 化学式: C₃₃H₂₆O₃
• 分子量: 470.568
• InChiKey: MCWICDQQCVEHHL-UHFFFAOYSA-N

物化性质

• 沸点：
  646.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diisopropyl (E)-azodicarboxylate 、 3-methoxy-4,6-bis(1,1-diphenylmethyl)-1,2-benzoquinone 在 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.0h， 以85%的产率得到5,7-Dibenzhydryl-4-methoxy-1-oxa-2,3-diaza-indan-2,3-dicarboxylic acid diisopropyl ester
  参考文献：
  名称：

  Reaction of Huisgen Zwitterion with 1,2-Benzoquinones and Isatins:  Expeditious Synthesis of Dihydro-1,2,3-benzoxadiazoles and Spirooxadiazolines

  摘要：

  The zwitterionic intermediate generated from dialkyl azodicarboxylate and triphenylphosphine on reaction with 3-methoxy-1,2-benzoquinones afforded dihydro-1,2,3-benzoxadiazoles. N-Substituted isatins furnished spirooxadiazolines under similar conditions.

  DOI：

  10.1021/ol051956n
• 作为产物：
  描述：

  3-甲氧基儿茶酚 在 sodium periodate 、 montmorillonite K-10 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 22.0h， 生成 3-methoxy-4,6-bis(1,1-diphenylmethyl)-1,2-benzoquinone
  参考文献：
  名称：

  SnCl₄-Catalyzed Reaction of o-Benzoquinones and Aryl Acetylenes:  An Unprecedented One-Pot Synthesis of Tropone Derivatives

  摘要：

  Highly substituted tropone derivatives were obtained as a result of SnCl4-catalyzed cycloaddition of 3-methoxy-substituted o-benzoquinones with aryl acetylenes and subsequent rearrangement of the adducts with concomitant decarbonylation.

  DOI：

  10.1021/jo016098x

文献信息

• Multicomponent reactions involving zwitterionic intermediates for the construction of heterocyclic systems: one pot synthesis of aminofurans and iminolactones
  作者：Vijay Nair、A.Unni Vinod、N Abhilash、Rajeev S Menon、V Santhi、R.Luxmi Varma、S Viji、Saumini Mathew、R Srinivas

  DOI：10.1016/j.tet.2003.10.052

  日期：2003.12

  The reaction of 1:1 zwitterionic intermediate generated in situ from dimethyl acetylenedicarboxylate (DMAD) and cyclohexyl isocyanide with aldehydes and quinones is described. The reaction of stoichiometric amounts of DMAD, isocyanide and aldehydes afforded 2-aminofurans in good yields, while the reaction with quinones gave iminolactones.

  描述了由乙炔二羧酸二甲酯（DMAD）和环己基异氰化物就地生成的1：1两性离子中间体与醛和醌的反应。化学计量的DMAD，异氰化物和醛的反应以良好的产率提供了2-氨基呋喃，而与醌的反应给出了亚氨基内酯。
• Triphenylphosphane-Mediated Addition of Dimethyl Acetylenedicarboxylate to 1,2- and 1,4-Benzoquinones: Synthesis of Novel γ-Spirolactones
  作者：Vijay Nair、J. Somarajan Nair、A. U. Vinod

  DOI：10.1055/s-2000-8212

  日期：——

  The zwitterionic intermediate, generated by the addition of triphenylphosphane to dimethyl acetylenedicarboxylate, undergoes facile addition to ortho- and para-quinones to afford highly functionalized novel unsaturated γ-spirolactones in moderate to high yields.

  由三苯基膦与二甲基乙炔二羧酸酯反应生成的两性离子中间体，容易与邻位和对位醌发生加成反应，得到高功能化的新型不饱和γ-螺环内酯，产率中等到较高。
• 1,3-Dipolar cycloaddition reactions of carbonyl ylides with 1,2-diones: synthesis of novel spiro oxabicycles
  作者：Vijay Nair、K.C Sheela、D Sethumadhavan、R Dhanya、Nigam P Rath

  DOI：10.1016/s0040-4020(02)00387-3

  日期：2002.5

  1,3-Dipolar cycloaddition reaction of carbonyl ylides with various o-quinones afforded highly oxygenated spiro oxabicycles.

  羰基化物与各种邻醌的1，3-偶极环加成反应提供了高度氧化的螺氧杂双环。
• The reaction of isoquinoline and dimethyl acetylenedicarboxylate with 1,2- and 1,4-benzoquinones: a novel synthesis of spiro[1,3]oxazino[2,3-a]isoquinolines
  作者：Vijay Nair、A.R Sreekanth、A.T Biju、Nigam P Rath

  DOI：10.1016/s0040-4039(02)02649-7

  日期：2003.1

  The 1,4-dipolar intermediate generated by the addition of isoquinoline to dimethyl acetylenedicarboxylate is trapped by 1,2- and 1,4-benzoquinones to afford spiro[1,3]oxazino[2,3-a]isoquinoline derivatives in high yields.

  通过将异喹啉添加到乙酰二羧酸二甲酯中而生成的1,4-偶极中间体被1,2-和1,4-苯醌捕获，从而以高收率提供螺[1,3]恶嗪基[2,3- a ]异喹啉衍生物。
• Novel 1,3-dipolar cycloaddition reaction of carbonyl ylide with o-quinones
  作者：Vijay Nair、K.C. Sheela、K.V. Radhakrishnan、Rath P. Nigam

  DOI：10.1016/s0040-4039(98)01065-x

  日期：1998.7

  1,3-Dipolar cycloaddition reaction of carbonyl ylide with o-quinones afforded novel highly oxygenated spirocyclic compounds.

  羰基内酯与邻醌的1，3-偶极环加成反应提供了新型的高度氧化的螺环化合物。