3-mesityl-4,6,7-trimethylbenzofuran | 126135-10-2

• 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: 3-mesityl-4,6,7-trimethylbenzofuran
• 英文别名: 3-mesityl-4,6,7-trimethylbenzofuran；4,6,7-Trimethyl-3-(2,4,6-trimethylphenyl)-1-benzofuran
• CAS: 126135-10-2
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: BXSNGECNPKAPRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2,2-dimesityl-vinyl alcohol 在 二氯二茂锆 、 tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate) 、 sodium hydride 作用下， 生成 3-mesityl-4,6,7-trimethylbenzofuran
  参考文献：
  名称：

  First characterisation of zirconium enolate radical cations in solution and their mesolytic bond cleavage to zirconocene cations

  摘要：

  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。

  DOI：

  10.1039/a708495a

文献信息

• Probing M−O Bond Cleavage in Silicon and Titanium Bisenolate Radical Cations
  作者：Michael Schmittel、Armin Burghart、Helmut Werner、Matthias Laubender、Rolf Söllner

  DOI：10.1021/jo981793z

  日期：1999.4.1

  In this study, several novel sterically congested silicon and titanium bisenolates of exceptional hydrolytic stability have been synthesized and characterized. The structure of the titanium bisenolate T2 could be determined by X-ray structure analysis. Preparative one-electron oxidation of the sterically shielded metal bisenolates S1-S4 and T1-T2 led to formation of the benzofurans B1 and B2. As the

  在这项研究中，已经合成和表征了几种新型的具有超强水解稳定性的空间拥挤的硅和钛双酚盐。可以通过X射线结构分析确定二烯酸钛T2的结构。空间屏蔽的金属双酚盐S1-S4和T1-T2的制备性单电子氧化导致苯并呋喃B1和B2的形成。由于苯并呋喃的形成是在初始自由基阳离子阶段发生MO键断裂过程的有力证据，因此我们能够使用循环伏安法（一级速率常数范围为k（f）= 0.1-90 s（-）（1））。这些数据表明，硅酸二苯酚和钛酸二苯酚盐都是氧化分子内碳-碳键形成过程的有趣候选物。
• 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。
• 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
  作者：Michael Schmittel、Juergen Heinze、Holger Trenkle

  DOI：10.1021/jo00114a020

  日期：1995.5

  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.
• Diastereoselective Enolate Coupling through Redox Umpolung in Silicon and Titanium Bisenolates:  A Novel Concept Based on Intramolecularization of Carbon−Carbon Bond Formation
  作者：Michael Schmittel、Armin Burghart、Wolfgang Malisch、Joachim Reising、Rolf Söllner

  DOI：10.1021/jo971650x

  日期：1998.1.1
• Schmittel, Michael; Baumann, Ulrich, Angewandte Chemie, 1990, vol. 102, # 5, p. 571 - 572
  作者：Schmittel, Michael、Baumann, Ulrich

  DOI：——

  日期：——