2-methyl-1,1-diphenylpropane-1,2-diol | 5344-64-9

• 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-methyl-1,1-diphenylpropane-1,2-diol
• CAS: 5344-64-9
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: NEBPKRZOOBQYIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-1,1-diphenylpropane-1,2-diol 在 对甲苯磺酸 作用下， 生成 3,3-diphenylbutan-2-one
  参考文献：
  名称：

  一锅跨品尼高耦合/重排程序

  摘要：

  一种新的催化复古-pinacol /交叉频哪醇反应，接着进行随后的重排或中间形成的邻位二醇的脱氧，进行说明。这种操作简单的一锅操作方案可分离出具有高收率和高选择性的双生α，α-二苯基酮或1,1-二苯基烯烃。

  DOI：

  10.1002/hlca.201200402
• 作为产物：
  描述：

  异丁酰苯 在 过甲酸 、 硫酸 、 水 作用下， 以 溶剂黄146 为溶剂， 生成 2-methyl-1,1-diphenylpropane-1,2-diol
  参考文献：
  名称：

  Reaktivit�t und Selektivit�t bei der Oxidation von Styrolderivaten. IV. Untersuchungen zur Oxidation von substituierten ?,?-Dimethylstyrolen

  摘要：

  The liquid phase oxidation of substituted (p-MeO-, p-Cl-, m-CF3-) 2-aryl-3-methyl-but-2-enes, of 1,1-diphenyl-2-methyl-propene, of 1-ethoxy-2-methyl-1-phenyl-propene and of 9-isopropylidene-fluorene with pure oxygen was investigated in chlorobenzene solution and in presence of cumene and of cumene hydroperoxide in the temperature range 65-125 degrees C. The product yields were determined gaschromatographically. The differences of the activation energies of epoxide formation and the parallel reactions were calculated. They amount to 19-48 kJ/mol. The epoxide selectivity increases with increasing temperature and increasing concentration of olefin. The relative chain propagation constants (k(pC=C)) were determined by competitive oxidation with cumene. The k(pC=C) values of substituted beta,beta-dimethylstyrenes can be correlated by a LFE-relationship with the ionisation energies of the olefins.

  DOI：

  10.1002/prac.19983400308

文献信息

• Ytterbium Metal Mediated Synthesis of Symmetrical and Unsymmetrical Pinacols from Carbonyl Compounds
  作者：Zhaomin Hou、Kan Takamine、Yuzo Fujiwara、Hiroshi Taniguchi

  DOI：10.1246/cl.1987.2061

  日期：1987.10.5

  Reaction of aromatic aldehydes and ketones with ytterbium metal gives the corresponding pinacols in high yields. Cross-coupling reaction of benzophenone with other carbonyl compounds to produce unsymmetrical pinacols is also described.

  芳香醛和酮与镱金属反应以高产率得到相应的频哪醇。还描述了二苯甲酮与其他羰基化合物产生不对称频哪醇的交叉偶联反应。
• Polymer-Mediated Pinacol Rearrangements
  作者：Michael Smith、Christopher Pavlik、Martha Morton

  DOI：10.1055/s-0030-1261148

  日期：2011.9

  Both poly(3,4-ethylenedioxythiophene) and poly(pyrrole) mediate a pinacol rearrangement of 1,2-diols. The yields of ketone or aldehyde products are comparable to those observed for treatment with mineral acids or Lewis acids. The advantage of this protocol is a two-phase reaction medium in hydrocarbon solvents that allows facile recovery of the products by simple filtration of the polymer and removal

  聚（3,4-乙撑二氧噻吩）和聚（吡咯）均介导1,2-二醇的频哪醇重排。酮或醛产物的产率与用无机酸或路易斯酸处理所观察到的产率相当。该方案的优点是在烃类溶剂中形成两相反应介质，可通过简单过滤聚合物和除去溶剂来轻松回收产物。聚合物和烃溶剂均可被回收并用于随后的反应中。 频哪醇-二醇-PEDOT-聚吡咯-重排
• Multiple-photon chemistry in the benzophenone photoreduction during laser-jet photolysis: Effect of alcohol solvent on cross-coupling versus hydrogen abstraction of the electronically excited hydroxydiphenylmethyl radical
  作者：Waldemar Adam、Barbara Walther

  DOI：10.1016/0040-4020(96)00576-5

  日期：1996.7

  The ground state of the hydroxydiphenylmethyl radical (1) leads to benzpinacol (2) through head-to-head coupling and the diols 3 as cross-coupling product. In contrast. under the high-intensity conditions of the laser-jet photolysis. the excited radical 1∗ couples in the para position to afford the benzophenone derivatives 4 (head-to-tail coupling) (higher spin density at the para position / AM1 calculations)

  羟基二苯基甲基自由基（1）的基态通过头对头偶合和作为交叉偶合产物的二醇3生成苯频哪醇（2）。相比之下。在高强度条件下进行激光喷射光解。激发的自由基1 *在对位偶合，得到二苯甲酮衍生物4（头尾耦合）（对位较高的自旋密度/ AM1计算）。主要的两个光子产物是苯甲酚（5）。从MeOH到i PrOH的氢原子抽象度明显增加1 *用电子激发的基团1 ∗相对于基态的更大的亲电特性来解释。
• Pinacol Rearrangement and Direct Nucleophilic Substitution of Allylic Alcohols Promoted by Graphene Oxide and Graphene Oxide CO₂H
  作者：Melania Gómez-Martínez、Alejandro Baeza、Diego A. Alonso

  DOI：10.1002/cctc.201601362

  日期：2017.3.20

  Graphene oxide (GO) and carboxylic acid functionalized GO (GO–CO2H) have been found to efficiently promote the heterogeneous and environmentally friendly pinacol rearrangement of 1,2‐diols and the direct nucleophilic substitution of allylic alcohols. In general, high yields and regioselectivities are obtained in both reactions using 20 wt % of catalyst loading and mild reaction conditions.

  已发现氧化石墨烯（GO）和羧酸官能化的GO（GO-CO 2 H）可有效促进1,2-二醇的异质和环境友好的频哪醇重排以及烯丙基醇的直接亲核取代。通常，使用20重量％的催化剂负载量和温和的反应条件，在两个反应中均获得高产率和区域选择性。
• Regioselective Organocatalytic Formation of Carbamates from Substituted Cyclic Carbonates
  作者：Sergio Sopeña、Victor Laserna、Wusheng Guo、Eddy Martin、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/adsc.201600290

  日期：2016.6.30

  A highly regioselective catalytic approach has been developed towards carbamates derived from cyclic organic carbonates by reaction of the latter with amine reagents under organocatalytic control. For various combinations of carbonate and amine substrates, an organocatalyst (TBD: 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene) was used to increase the reaction kinetics while exerting excellent regioselective control

  通过在有机催化控制下使环状有机碳酸酯与胺试剂反应，已经开发了对来自环状有机碳酸酯的氨基甲酸酯的高度区域选择性催化方法。对于碳酸盐和胺底物的各种组合，使用有机催化剂（TBD：1,5,7-三氮杂双环[4.4.0] dec-5-烯）来提高反应动力学，同时进行出色的区域选择性控制。当前的方法是使用多种易于获得的取代有机碳酸酯控制该反应的区域选择性的第一种通用方法。