2-tert-butyl-3-mesityl-4,6,7-trimethylbenzofuran | 126135-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-tert-butyl-3-mesityl-4,6,7-trimethylbenzofuran
• 英文别名: 2-tert-butyl-3-mesityl-4,6,7-trimethylbenzo[b]furan；2-Tert-butyl-4,6,7-trimethyl-3-(2,4,6-trimethylphenyl)-1-benzofuran
• CAS: 126135-09-9
• 化学式: C₂₄H₃₀O
• 分子量: 334.502
• InChiKey: GXICOOCHUDGJQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-Acetoxy-1,1-dimesityl-3,3-dimethyl-1-butene 在 tris(1,10-phenanthroline)iron(III) hexafluorophosphate 作用下， 以 乙腈 为溶剂， 生成 2-tert-butyl-3-mesityl-4,6,7-trimethylbenzofuran
  参考文献：
  名称：

  Electroactive Protecting Groups and Reaction Units. Part 1. Mesolytic Cleavage of the O-CO Bond in Enol Acetate Cation Radicals with Direct Formation of .alpha.-Carbonyl Cations. Mechanistic and Synthetic Aspects

  摘要：

  For the first time, enol ester cation radicals are reversibly monitored in a cyclic voltammetry experiment. Preparative one-electron oxidation of enol acetates A1-A4 leads to the formation of benzofurans B1-B4 through mesolytic O-CO bond fragmentation to alpha-carbonyl cations and the acetyl radical. With A3(.+), the kinetics of the O-CO bond cleavage was investigated by cyclic voltammetry, providing Delta H double dagger = 17.0 kcal mol(-1) and Delta S double dagger = 11 cal mol(-1) K-1 in dichloromethane. The slightly increased rate of bond dissociation upon addition of acetonitrile is explained with charge localization in the transition state rather than with a solvent-assisted bond cleavage mechanism. The occurrence of curve crossings and isopotential points in the cyclic voltammograms of the model compounds A1-A4 at low scan rates can be rationalized by a multiparameter reaction scheme based on an ECCE(DISP) mechanism, digital simulation of which confirmed the cleavage selectivity and allowed for the determination of the involved rate constants of the homogeneous chemical reaction steps.

  DOI：

  10.1021/jo00114a020

文献信息

• First characterisation of zirconium enolate radical cations in solution and their mesolytic bond cleavage to zirconocene cations
  作者：Michael Schmittel、Rolf Söllner

  DOI：10.1039/a708495a

  日期：——

  Zirconocene enolate radical cations are generated and characterised in solution for the first time; the sterically congested radical cations undergo a mesolytic Zr–O bond cleavage process yielding zirconocene cations, the kinetics of which are determined.

  首次在溶液中生成锆烯烯酮自由基阳离子并对其进行表征；立体拥塞的自由基阳离子经过介解 Zr-O 键裂解过程生成锆烯阳离子，并确定了其动力学。
• Radical Cation Ester Cleavage in Solution. Mechanism of the Mesolytic O−CO Bond Scission
  作者：Michael Schmittel、Karl Peters、Eva-Maria Peters、Andreas Haeuseler、Holger Trenkle

  DOI：10.1021/jo0057093

  日期：2001.5.1

  ester radical cations is characterized in solution by cyclic voltammetry and EPR spectroscopy. Preparative transformations using one-electron oxidants or anodic oxidation yield benzofurans after O-CO bond cleavage. Mechanistic investigations and direct detection of radical intermediates reveal that all enol radical cations undergo exclusively O-CO bond cleavage to provide alpha-carbonyl cations and acyl

  在溶液中通过循环伏安法和EPR光谱法表征了广泛的烯醇式碳酸酯，氨基甲酸酯和酯自由基阳离子。使用单电子氧化剂或阳极氧化的制备型转化在O-CO键断裂后产生苯并呋喃。自由基中间体的机理研究和直接检测表明，所有烯醇自由基阳离子都经过O-CO键裂解，分别提供α-羰基阳离子和酰基（或烷氧基酰基和氨酰基）自由基。使用快速扫描循环伏安法已经确定了介观裂解的动力学和亲核添加剂的影响。
• A rearranged acetylene from an E1 solvolysis of a substituted α-trimethylsilylvinyl system
  作者：Elana Zipori、Zvi Rappoport

  DOI：10.1016/0040-4039(91)80177-8

  日期：1991.10

  The reaction of Mes2CC(OH)SiMe2R (RMe, SiMe3) with SOCl2 gives the rearranged elimination product MesCCMes, presumably via β-mesityl participation in the solvolysis of the derived OSOCl derivative, followed by “Me3Si+“ loss from the rearranged ion MesC(Me3Si)C-Mes. Under the same conditions, the carbon analogue Mes2CC(OH)Bu-t gives the ketone Mes2CHCOBu-t and benzofurans via non-solvolytic reactions

  ME的反应2 CC（OH）森达2 R（RMe，森达3）用的SOCl 2给出了重排的消除产物MesCCMes，通过在派生OSOCl衍生物的溶剂解β-基参与推测，随后重排离子MesC（Me 3 Si）C-Mes引起的“ Me 3 Si + ”损失。在相同条件下，碳类似物的Mes 2 CC（OH）卜叔给出了酮的Mes 2经由非溶剂化反应CHCOBu-t和苯并呋喃。
• Zirconium enolate radical cations in solution—characterisation and kinetics of their mesolytic Zr–O bond cleavage †
  作者：Michael Schmittel、Rolf Söllner

  DOI：10.1039/a808400i

  日期：——

  zirconocene enolate radical cations and one hydroquinone biszirconocene radical cation have been generated and characterised in solution by standard and fast scan cyclic voltammetry. The electroanalytical results along with those from product analysis of preparative one-electron oxidations indicate that the sterically congested radical cations undergo a mesolytic Zr–O bond cleavage process. The kinetics of

  生成了六个锆茂烯烯酸酯自由基阳离子和一个对苯二酚双锆茂烯自由基阳离子，并通过标准和快速扫描循环伏安法在溶液中进行了表征。电分析结果以及制备型单电子氧化产物分析得出的结果表明，空间拥挤的自由基阳离子经历了Zr-O键的介解过程。所述mesolytic的Zr-O键断裂产生锆茂阳离子和寿命（动力学吨½在室温下在二氯甲烷中的锆烯醇化物自由基阳离子的）被确定。
• One-electron oxidation of enol phosphates, enol phosphites and enol phosphinates. Evidence for an unprecedented P–O bond cleavage in phosphoenol radical cations in solution¹
  作者：Michael Schmittel、Jens-Peter Steffen、Armin Burghart

  DOI：10.1039/cc9960002349

  日期：——

  For the first time phosphoenol radical cations are generated in solution and monitored by cyclic voltammetry and EPR; the sterically congested radical cations undergo an unprecedented P-O bond cleavage, the kinetics of which are determined.