4-(tert-butyl)-3-methoxycyclohexa-3,5-diene-1,2-dione | 212055-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(tert-butyl)-3-methoxycyclohexa-3,5-diene-1,2-dione
• 英文别名: 3-methoxy-4-tert-butyl-1,2-benzoquinone；5-methoxy-4-tert-butyl-1,2-benzoquinone；4-Tert-butyl-3-methoxycyclohexa-3,5-diene-1,2-dione
• CAS: 212055-88-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: ZVXIUZHGVBEPGV-UHFFFAOYSA-N

物化性质

• 沸点：
  294.5±40.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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 、 4-(tert-butyl)-3-methoxycyclohexa-3,5-diene-1,2-dione 在 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.0h， 以94%的产率得到5-tert-Butyl-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：

  4-Tert-butyl-3-methoxybenzene-1,2-diol 在 sodium periodate 作用下， 生成 4-(tert-butyl)-3-methoxycyclohexa-3,5-diene-1,2-dione
  参考文献：
  名称：

  Efficient Diels–Alder Reaction of 1,2-Benzoquinones with Arynes and Its Utility in One-Pot Reactions

  摘要：

  A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.

  DOI：

  10.1021/ol302997q

文献信息

• Air oxygenation chemistry of 4-TBC catalyzed by chloro bridged dinuclear copper(<scp>ii</scp>) complexes of pyrazole based tridentate ligands: synthesis, structure, magnetic and computational studies
  作者：Ishita Banerjee、Pabitra Narayan Samanta、Kalyan Kumar Das、Rodica Ababei、Marguerite Kalisz、Adrien Girard、Corine Mathonière、M. Nethaji、Rodolphe Clérac、Mahammad Ali

  DOI：10.1039/c2dt30983a

  日期：——

  bis(μ-Cl) bridged copper(II) complexes, [Cu2(μ-Cl)2(LX)2](ClO4)2 (LX = N,N-bis[(3,5-dimethylpyrazole-1-yl)-methyl]benzylamine with X = H(1), OMe(2), Me(3) and Cl(4)), have been synthesized and characterized by the single crystal X-ray diffraction method. In these complexes, each copper(II) center is penta-coordinated with square-pyramidal geometry. In addition to the tridentate LX ligand, a chloride ion

  四个双核双（μ-Cl）桥连的铜（II）配合物[Cu 2（μ-Cl）2（L X）2 ]（ClO 4）2（L X =N，N-双[[（3,5-二甲基吡唑-1-基）-甲基]苄胺X ＝ H（1），OMe（2），Me（3）和Cl（4））已经通过单晶X射线衍射法合成并表征。在这些络合物中，每个铜（II）中心都与方形金字塔形几何形状五角坐标。除三齿L X配体外，氯离子占据正方形平面的最后位置。该氯离子还在其轴向位置上键合至相邻的Cu（II）部位，形成SP- I双核Cu（II）单元，该单元显示出较小的分子内铁磁相互作用，并得到DFT计算的支持。配合物1-3表现出甲基单加氧酶（p MMO）行为并氧化4-叔丁基邻苯二酚（4-TBCH 2）与分子氧甲醇或MeCN 4-叔丁基苯醌（4- TBQ），5-甲氧基-4-叔丁基苯醌（5-的MeO-4-TBQ）与6,6'-卜沿着主要产物吨-联苯-3,4,3'，4 ' -四醇等
• 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。
• 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。
• Ganga; Suresh; Suresh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 7, p. 1071 - 1079
  作者：Ganga、Suresh、Suresh、Varma, R. Luxmi

  DOI：——

  日期：——
• Sterically encumbered regioselective cycloaddition of a calixarene derived bis(spirodienone) with 1,2-benzoquinones
  作者：R. Luxmi Varma、V.B. Ganga、E. Suresh、C.H. Suresh

  DOI：10.1016/j.tetlet.2005.11.151

  日期：2006.2

  A calix[4]arene derived bis(spirodienone) acts as the 2 pi component in a cycloaddition reaction with two molecules of 3,5di-tert-butyl-1-2-benzoquinone in the [2+4] manner leading to macrocycles with a benzodioxin moiety. A theoretical rationalization of the results suggested a sterically encumbered regioselective pathway, which gives sterically crowded products. (c) 2005 Elsevier Ltd. All rights reserved.