2-ethoxy-3,6-di-tert-butylphenoxy radical | 852574-88-0

• 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: 2-ethoxy-3,6-di-tert-butylphenoxy radical
• 英文别名: 3,6-di-tert-butyl-2-ethoxyphenoxy radical；3,6-di-tert-butyl-2-ethoxyphenoxyl
• CAS: 852574-88-0
• 化学式: C₁₆H₂₅O₂
• 分子量: 249.373
• InChiKey: WUQFOGGZIXBNQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  10.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethoxy-3,6-di-tert-butylphenoxy radical 以 甲苯 为溶剂， 生成 3,6-di-tert-butyl-4-(3,6-di-tert-butyl-2-ethoxyphenoxy)-2-ethoxycyclohexa-2,5-dienone
  参考文献：
  名称：

  The oxidation of 2-alkoxy-3,6-di-tert-butylphenols. The reversible dimerization of 2-alkoxy-3,6-di-tert-butylphenoxy radicals

  摘要：

  The oxidation of 2-alkoxy-3,6-di-tert-butylphenols has been studied. It was found that 2-RO-3,6-di-tert-butylphenoxy radicals (R = Et, Pr, Ph) undergo dimerization by C-O coupling. The X-ray structure of 2-ethoxy-3,6-di-tert-butylphenoxy dimer has been determined. Radical dimers dissociate reversibly in solution to give two phenoxy radicals at 200-350 K. By using EPR spectroscopy the equilibrium concentration of the phenoxy radicals, equilibrium constants and AH and AS of dissociation have been determined. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.012
• 作为产物：
  描述：

  2-ethoxy-3,6-di-tert-butylphenol 在 氢氧化钾 、 potassium hexacyanoferrate(III) 作用下， 以 乙醚 、 水 为溶剂， 反应 0.5h， 生成 2-ethoxy-3,6-di-tert-butylphenoxy radical
  参考文献：
  名称：

  The oxidation of 2-alkoxy-3,6-di-tert-butylphenols. The reversible dimerization of 2-alkoxy-3,6-di-tert-butylphenoxy radicals

  摘要：

  The oxidation of 2-alkoxy-3,6-di-tert-butylphenols has been studied. It was found that 2-RO-3,6-di-tert-butylphenoxy radicals (R = Et, Pr, Ph) undergo dimerization by C-O coupling. The X-ray structure of 2-ethoxy-3,6-di-tert-butylphenoxy dimer has been determined. Radical dimers dissociate reversibly in solution to give two phenoxy radicals at 200-350 K. By using EPR spectroscopy the equilibrium concentration of the phenoxy radicals, equilibrium constants and AH and AS of dissociation have been determined. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.012

文献信息

• Multiple Reactivity of Sn ^II Complexes Bearing Catecholate and <i>o</i> ‐Amidophenolate Ligands
  作者：Maxim G. Chegerev、Alexander V. Piskunov、Aryna V. Maleeva、Georgy K. Fukin、Gleb A. Abakumov

  DOI：10.1002/ejic.201600501

  日期：2016.8

  The reactivity of tin(II) catecholate complex CatSn (1) (where Cat = 3,6‐di‐tert‐butylcatecholate dianion) and two o‐amidophenolate complexes DippAPSn (2) and PhAPSn (3) [where DippAP = 4,6‐di‐tert‐butyl‐N‐(2,6‐diisopropylphenyl)amidophenolate; PhAP = 4,6‐di‐tert‐butyl‐N‐(phenyl)amidophenolate dianions] towards different reagents is reported. Products of the insertion of 1 and 2 into the S–S bond of

  儿茶酚酸锡（II）配合物CatSn（1）（其中Cat = 3,6-二叔丁基儿茶酚酸二阴离子）和两个邻氨基苯酚酸酯配合物Dipp APSn（2）和Ph APSn（3）[其中Dipp AP = 4,6-二-叔丁基- ñ - （2,6-二异丙基）amidophenolate; pH值AP = 4,6-二-叔丁基- ñ报道（苯基）amidophenolate二价阴离子]朝向不同的试剂- 。插入1和2的乘积获得了四甲基秋兰姆二硫化物的S–S键，并通过X射线衍射分析对其进行了表征。配合物1和2被2-乙氧基-3,6-二叔丁基苯氧基自由基的低温氧化使我们能够检测到形成具有氧化还原活性配体自由基阴离子形式的顺磁性锡（II）衍生物的形成。锡衍生物3与Ni（CO）4的反应导致后者中一个CO基团的取代，并形成了新的双金属产物。
• O,N-Heterocyclic germylenes as efficient catalysts for hydroboration and cyanosilylation of benzaldehyde
  作者：Kseniya V. Arsenyeva、Kira I. Pashanova、Olesya Yu. Trofimova、Irina V. Ershova、Maxim G. Chegerev、Alyona A. Starikova、Anton V. Cherkasov、Mikhail A. Syroeshkin、Anna Ya. Kozmenkova、Alexandr V. Piskunov

  DOI：10.1039/d1nj01644j

  日期：——

  6-di-isopropylphenyl) towards hydroboration and cyanosilylation of benzaldehyde was examined. Germylene 1 demonstrates the most potent promoter properties for such reactions, which allowed cyanosilylation and hydroboration of aldehyde under mild conditions with excellent conversion quickly. Theoretical studies were performed to establish the mechanism, and different reaction routes were examined. According

  新单体O，N-杂环锗烯广告APGE（1基于4,6-二- ）叔丁基- ñ -adamantyl- ö氨基苯酚合成和结构表征。晶体中的锗烯1表现出相邻分子之间弱的 Ge⋯Ge 相互作用。使用循环伏安法和苯氧基自由基的化学氧化研究了化合物1及其已知类似物Ph APGe ( 2 )、t- Bu APGe ( 3 )的氧化还原活性。Germylene 1，相对于2和3, 发现在氧化过程中形成相对稳定的o-亚氨基半醌酸酯部分。最后一种是通过 EPR 光谱在低温甲苯溶液中检测到的。检测了锗烯1-3和dipp APGe ( 4 ) (dipp – 2,6-二异丙基苯基) 对苯甲醛的硼氢化和氰基硅烷化的催化活性。锗烯1证明了此类反应最有效的促进剂特性，允许在温和条件下进行醛的氰基硅烷化和硼氢化反应，并具有极好的转化速度。进行了理论研究以建立机制，并检查了不同的反应路线。根据 DFT (B3LYP/def2-SVP)
• New lead(II) catecholate and o-semiquinone complexes
  作者：G. A. Abakumov、V. K. Cherkasov、A. V. Piskunov、A. V. Lado、G. K. Fukin、L. G. Abakumova

  DOI：10.1007/s11172-006-0391-z

  日期：2006.7

  Lead(II) catecholate complexes were prepared by reduction of 3,6-di-tert-butyl-o-benzoquinone and its derivatives with lead metal in THF. The molecular structure of the (CatPb)4·(PbO)2·6C3H6O complex (Cat is the dianion of 3,6-di-tert-butylcatechol), which was synthesized by hydrolysis of lead 3,6-di-tert-butylcatecholate in acetone, was established by X-ray diffraction. A series of lead(II) o-semiquinone complexes, which were prepared by the addition of the phenoxyl radical to lead catecholates or by oxidation of the latter with mercury(II), copper(II), or silver(I) halides, were studied by the ESR method. Lead(II) mono-o-semiquinolate complexes undergo symmetrization to form stable bis-o-semiquinolates, which were isolated and characterized in individual state.

  通过在四氢呋喃中还原 3,6-二叔丁基邻苯醌及其衍生物与金属铅制备儿茶酚铅 (II) 络合物。由3,6-二叔丁基儿茶酚铅水解合成的(CatPb)4·(PbO)2·6C3H6O配合物（Cat是3,6-二叔丁基儿茶酚的双阴离子）的分子结构在丙酮中，通过X射线衍射确定。一系列邻半醌铅 (II) 络合物是通过将苯氧基自由基加成到儿茶酚酸铅上或通过用卤化汞 (II)、铜 (II) 或银 (I) 卤化物氧化后者来制备的。采用ESR法进行研究。单邻半喹啉铅 (II) 络合物经过对称化形成稳定的双邻半喹啉盐，并在单独状态下进行分离和表征。
• Free radical fixation by tin(IV) diphenylcatecholate complexes
  作者：A. V. Lado、A. V. Piskunov、V. K. Cherkasov、G. K. Fukin、G. A. Abakumov

  DOI：10.1134/s1070328406030031

  日期：2006.3

  The reactions of sodium and thallium catecholates CatM(2) (Cat is the 3.6-di-tert-butylpyrocatechol dianion; M = Na, Tl) with tin diphenyl dichloride afford new tin catecholate complexes Ph(2)SnCat center dot THF (I) and Ph(2)SnCat (II). The molecular structure of pentacoordinated complex I is determined by X-ray diffraction analysis. The synthesized complexes are capable of fixating both short-lived (PhC(O)O-center dot, (CH3)(2)NC(S)S-center dot, and NC(CH3)(2)C-center dot) and stable free radicals (aroxyl, nitroxyl, triphenylmethyl, and phenoxazinyl) to form stable o-semiquinone tin derivatives.