5,5'-di-tert-butyl-2,2'-dimethyl-3,3',4,4'-tetrahydrobiphenyl-3,3',4,4'-tetraone | 196501-93-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5,5'-di-tert-butyl-2,2'-dimethyl-3,3',4,4'-tetrahydrobiphenyl-3,3',4,4'-tetraone
• 英文别名: 2,2'-dimethyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinones；4,4'-bis(3-methyl-3-tert-butyl-1,2-benzoquinone)；4,4'-di-(3-methyl-6-tert-butyl-o-benzoquinone)；4,4'-bi(3-methyl-6-tert-butyl-o-benzoquinone)；4,4'-(3-methyl-6-tert-butyl-o-benzoquinone)；5,5'-Di-t-butyl-2,2'-dimethylbiphenyl-3,4,3',4'-diquinone；6-tert-butyl-4-(5-tert-butyl-2-methyl-3,4-dioxocyclohexa-1,5-dien-1-yl)-3-methylcyclohexa-3,5-diene-1,2-dione
• CAS: 196501-93-6
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: IPAWEBMSVGDKPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-di-tert-butyl-2,2'-dimethyl-3,3',4,4'-tetrahydrobiphenyl-3,3',4,4'-tetraone 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  The binuclear trimethyl/triethylantimony(V) bis-catecholate derivatives of four-electron reduced 4,4′-di-(3-methyl-6-tert-butyl-o-benzoquinone)

  摘要：

  The reaction of 4,4`-di-(3-methyl-6-tert-butyl-o-benzoquinone) (Q-Q) with trimethyl- or triethylstibine proceeds as a two-electron oxidative addition of each quinone moiety and allows to prepare binuclear bis-catecholates R(3)Sb(Cat-Cat)SbR(3) with a nearly quantitative yield (R = Me, 1; R = Et, 2). The products 1 and 2 were characterized by IR-, (1)H and (13)C NMR spectroscopy. Molecular structure of triethylantimony (V) bis-catecholate 2 was confirmed by single-crystal X-ray analysis. Each Sb(V) atom adopts square pyramidal geometry with Cat moiety in basal positions, dihedral angle between Cat fragments is 74.27 (5)degrees. The oxidation of bis-catecholates by ferrocenium tetrafluoroborate or tetrabromo-p-benzoquinone leads to loss of one trialkylantimony(V) moiety forming paramagnetic salts containing one-side decoordinated mononuclear semiquinone-catecholato [R(3)Sb(Cat-SQ)](-) anion detected by EPR. The oxidation of 1 by air oxygen allows to prepare mononuclear quinone-catecholate Me(3)Sb(Cat-Q) (3). (c) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.09.008
• 作为产物：
  描述：

  在 硝酸 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 5,5'-di-tert-butyl-2,2'-dimethyl-3,3',4,4'-tetrahydrobiphenyl-3,3',4,4'-tetraone
  参考文献：
  名称：

  New sterically hindered di-o-quinones of the biphenyl series

  摘要：

  New di-o-quinones of the biphenyl series, namely, 2,2'-dialkyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinones, were synthesized. Their structures were established by IR and NMR spectroscopy. The molecular structure of 2,2'-dimethyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinone was established by X-ray structural analysis. The structure is characterized by orthogonal (the torsion angle is 82.9 degrees) mutual arrangement of o-benzoquinone fragments. ESR studies demonstrated that chemical reduction of diquinone proceeds in four one-electron stages to form paramagnetic mono- and trianions as intermediates. Quinopyrocatechols, which are intermediates in the synthesis of di-o-quinones, were isolated and characterized.

  DOI：

  10.1007/bf02495211

文献信息

• Oxidative addition reaction of o-quinones to triphenylantimony: novel triphenylantimony catecholate complexes
  作者：Vladimir K. Cherkasov、Ekaterina V. Grunova、Andrey I. Poddel’sky、Georgy K. Fukin、Yury A. Kurskii、Ludmila G. Abakumova、Gleb A. Abakumov

  DOI：10.1016/j.jorganchem.2004.11.049

  日期：2005.3

  New catecholate Sb(V) complexes triphenyl(3,6-di-tert-butylcatecholato)antimony(V) Ph3Sb(3,6-DBCat) (1) and triphenyl(perchloroxanthrenecatecholato)antimony(V) Ph3Sb(OXCatCl) (2) were synthesized by the oxidative addition reaction of corresponding o-quinones (3,6-di-tert-butyl-o-benzoquinone and perchloroxanthrenequinone-2,3) with triphenylantimony. Catecholates 1 and 2 can alternatively be synthesized

  新的儿茶酚酸Sb（V）络合三苯基（3,6-二叔丁基邻苯二酚）锑（V）Ph 3 Sb（3,6-DBCat）（1）和三苯基（全氯氧杂邻苯二酚）锑（V）Ph 3 Sb（OX）猫氯）（2）通过相应的氧化加成反应合成ø -quinones（3,6-二-叔丁基- ö苯醌和perchloroxanthrenequinone-2,3）与三苯基。儿茶酚酯1和2或者可以通过使适当的儿茶酚al与三苯基三氯化锑反应来合成。等摩尔比的4,4'-二-（3-甲基-6-叔丁基-邻苯并醌）和三苯基锑的氧化加成反应生成4-（2-甲基-5-叔丁基-环己二烯-1 ，5-dion-3,4-yl）-（3-甲基-6-叔丁基-邻苯二酚）三苯基锑（V）Ph 3 Sb（Cat-Q）（3）; 如果摩尔比为1：2，则复合物4,4'-二-[（（3-甲基-6-叔丁基-邻苯二酚）三苯基锑（V）] Ph 3 Sb（Cat-Cat）SbPh 3（4）的结果。复杂1
• Kinetics of photolytic transformations of 4,4′-Bi(3-methyl-6-tert-butyl-o-benzoquinone)
  作者：O. G. Mishchenko、S. V. Maslennikov、I. V. Spirina、N. O. Druzhkov、Yu. A. Kurskii、V. P. Maslennikov

  DOI：10.1134/s1070363207120110

  日期：2007.12

  The quantum yields and apparent rate constants of the photolysis of 4,4'-bi(3-methyl-6-tert-butyl-o-benzoquinone) and of accumulation of its transformation products in hydrocarbon solutions under the action of light with lambda 313 and 405 nm were determined. The probable scheme of photochemical reactions was suggested.
• Abakumov, Gleb A.; Cherkasov, Vladimir K.; Nevodchikov, Vladimir I., Inorganic Chemistry, 1998, vol. 37, # 23, p. 6117 - 6119
  作者：Abakumov, Gleb A.、Cherkasov, Vladimir K.、Nevodchikov, Vladimir I.、Kuropatov, Vyacheslav A.、Noll, Bruce C.、Pierpont, Cortlandt G.

  DOI：——

  日期：——
• Stereoselective synthesis of fused heterocycles from substituted o-Benzoquinones and anilines
  作者：Yu. A. Kurskii、N. O. Druzhkov、T. N. Kocherova、A. S. Shavyrin、V. K. Cherkasov、G. A. Abakumov

  DOI：10.1134/s1070428014010175

  日期：2014.1

  The reaction of trisubstituted o-benzoquinones with substituted anilines gives unstable o-benzoquinone imines which undergo intramolecular cyclization to 4aH-phenoxazine derivatives. Dimerization of the latter according to Diels-Alder yields complex heterocyclic systems, 7a,14a,15a,15b-tetrahydro-14,16-dioxa-5,9-diaza-8,15-ethenohexaphenes. Effective shielding of the carbonyl groups in 3,6-di-tert-butyl-4-isopropyl-o-benzoquinone makes it inactive toward substituted anilines.
• The binuclear trimethyl/triethylantimony(V) bis-catecholate derivatives of four-electron reduced 4,4′-di-(3-methyl-6-tert-butyl-o-benzoquinone)
  作者：Andrey I. Poddel’sky、Nikolay V. Somov、Nikolay O. Druzhkov、Vladimir K. Cherkasov、Gleb A. Abakumov

  DOI：10.1016/j.jorganchem.2010.09.008

  日期：2011.1

  The reaction of 4,4`-di-(3-methyl-6-tert-butyl-o-benzoquinone) (Q-Q) with trimethyl- or triethylstibine proceeds as a two-electron oxidative addition of each quinone moiety and allows to prepare binuclear bis-catecholates R(3)Sb(Cat-Cat)SbR(3) with a nearly quantitative yield (R = Me, 1; R = Et, 2). The products 1 and 2 were characterized by IR-, (1)H and (13)C NMR spectroscopy. Molecular structure of triethylantimony (V) bis-catecholate 2 was confirmed by single-crystal X-ray analysis. Each Sb(V) atom adopts square pyramidal geometry with Cat moiety in basal positions, dihedral angle between Cat fragments is 74.27 (5)degrees. The oxidation of bis-catecholates by ferrocenium tetrafluoroborate or tetrabromo-p-benzoquinone leads to loss of one trialkylantimony(V) moiety forming paramagnetic salts containing one-side decoordinated mononuclear semiquinone-catecholato [R(3)Sb(Cat-SQ)](-) anion detected by EPR. The oxidation of 1 by air oxygen allows to prepare mononuclear quinone-catecholate Me(3)Sb(Cat-Q) (3). (c) 2010 Elsevier B.V. All rights reserved.