2-(4-甲基苯基)-1,2-丙烷二醇 | 88416-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-甲基苯基)-1,2-丙烷二醇
• 中文别名: 2-(4-甲基苯基)丙烷-1,2-二醇
• 英文名称: 2-(p-tolyl)propane-1,2-diol
• 英文别名: 2-(p-Tolyl)-1,2-propanediol；2-(4-methylphenyl)propane-1,2-diol
• CAS: 88416-64-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: JVSJDMWWPVKLEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2905399090

反应信息

• 作为反应物：
  描述：

  2-(4-甲基苯基)-1,2-丙烷二醇 在 硫酸 作用下， 生成 2-(对甲苯基)丙醛
  参考文献：
  名称：

  Tiffeneau, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1903, vol. 137, p. 1261

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(对甲苯基)丙醛 在 sodium tetrahydroborate 、 N-(4-nitrobenzenesulfonyl)-3,3-dimethyloxaziridine 、 C₂₅H₂₆N₂O 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 2-(4-甲基苯基)-1,2-丙烷二醇
  参考文献：
  名称：

  A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes

  摘要：

  A new primary amine catalyst for the asymmetric a-hydroxylation and a-fluorination of alpha-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for a-functionalizations. Promising initial results in alpha-amination and alpha-chlorination reactions support this hypothesis.

  DOI：

  10.1021/acs.orglett.5b01193

文献信息

• Heterogeneous carbon nitride photocatalyst for C–C bond oxidative cleavage of vicinal diols in aerobic micellar medium
  作者：Tengfei Niu、Shengjun Chen、Mei Hong、Tianhao Zhang、Jiayang Chen、Xinyu Dong、Bangqing Ni

  DOI：10.1039/d0gc01727b

  日期：——

  A green and efficient visible-light promoted aerobic oxidative C–C bond cleavage of vicinal diols in micellar medium has been developed. This protocol used graphitic carbon nitride with nitrogen vacancies (CN620) as a metal-free recyclable photocatalyst and CTAB as surfactant in water. Control experiments and the ESR results indicated that superoxide radicals and valence band holes played an important

  已经开发了绿色高效的可见光促进胶束介质中邻二醇的好氧氧化C–C键裂解。该协议使用具有氮空位的石墨氮化碳（CN620）作为无金属可循环使用的光催化剂，而CTAB作为水中的表面活性剂。对照实验和ESR结果表明，超氧自由基和价带孔在反应中起重要作用。进一步的同位素实验提出了反应的β-分裂/ HAT途径和氧化/水解/脱水途径，这与以前的报道不同。半导体/胶束催化剂体系可以循环使用至少10次，而不会显着降低活性。此外，
• Homogeneous and heterogeneous photoredox-catalyzed hydroxymethylation of ketones and keto esters: catalyst screening, chemoselectivity and dilution effects
  作者：Axel G Griesbeck、Melissa Reckenthäler

  DOI：10.3762/bjoc.10.114

  日期：——

  The homogeneous titanium- and dye-catalyzed as well as the heterogeneous semiconductor particle-catalyzed photohydroxymethylation of ketones by methanol were investigated in order to evaluate the most active photocatalyst system. Dialkoxytitanium dichlorides are the most efficient species for chemoselective hydroxymethylation of acetophenone as well as other aromatic and aliphatic ketones. Pinacol coupling is the dominant process for semiconductor catalysis and ketone reduction dominates the Ti(OiPr)₄/methanol or isopropanol systems. Application of dilution effects on the TiO₂ catalysis leads to an increase in hydroxymethylation at the expense of the pinacol coupling.

  通过甲醇进行的均相钛和染料催化以及非均相半导体颗粒催化的酮类光羟甲基化反应进行了研究，以评估最活跃的光催化剂体系。二烷氧基钛二氯化物是对苯乙酮以及其他芳香族和脂肪族酮类进行化学选择性羟甲基化的最有效物种。对于半导体催化来说，邻苯二醇偶联是主要过程，而酮类还原主导着Ti(OiPr)₄/甲醇或异丙醇体系。在TiO₂催化中应用稀释效应会导致羟甲基化增加，而邻苯二醇偶联减少。
• Photo‐Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water
  作者：Yusuke Masuda、Daichi Ikeshita、Masahiro Murakami

  DOI：10.1002/hlca.202000228

  日期：2021.3

  Herein reported is a photo‐induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane‐2,3‐dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.

  本文报道的是在温和的反应条件下从烯烃光诱导生产邻二醇。目前使用二乙酰（=丁烷-2,3-二酮），氧​​气和水的二羟基化方法可免除有毒试剂并产生难处理的废物。
• Homogeneous catalytic oxidation of styrene and styrene derivatives with hydrogen peroxide in the presence of transition metal-substituted polyoxotungstates
  作者：Tiago A. G. Duarte、Ana C. Estrada、Mário M. Q. Simões、Isabel C. M. S. Santos、Ana M. V. Cavaleiro、M. Graça P. M. S. Neves、José A. S. Cavaleiro

  DOI：10.1039/c4cy00702f

  日期：——

  [XW11M(H2O)O39](n−m)−, where X = P, B or Si and M = Mn, Fe or Co, were evaluated as catalysts in the oxidation of styrene, α-methylstyrene, p-methylstyrene, α,p-dimethylstyrene, p-chlorostyrene, p-nitrostyrene, and p-methoxystyrene under mild conditions, using aqueous H2O2 as an eco-sustainable oxidant. In this study, the influence of the catalysts and of the different styrene substituents on the oxidation reaction

  通式为[XW 11 M（H 2 O）O 39 ] （n - m）-的Keggin型多氧钨酸盐的四丁基铵（TBA）盐，其中X = P，B或Si，M = Mn，Fe或Co ，被评价为在苯乙烯，α甲基苯乙烯，的氧化催化剂p甲基苯乙烯，α，p -dimethylstyrene，p -chlorostyrene，p硝基苯乙烯，和p温和的条件下-methoxystyrene，使用水性ħ 2 ö 2作为一种生态可持续的氧化剂。在这项研究中，根据转化率和选择性评估了催化剂和不同苯乙烯取代基对氧化反应曲线的影响。对于所有进行的催化研究，主要产物是由乙烯基双键的氧化裂解产生的，除了在用BW 11 Mn催化的对甲氧基苯乙烯氧化的情况下，对甲氧基苯酚是主要产物。催化剂BW 11 Mn和SiW 11 Co几乎对所有底物都具有100％的转化率，除了对-甲氧基苯乙烯和对-硝基苯乙烯以及α，p-二甲基苯乙烯仅在BW 11
• Resolution of Diols via Catalytic Asymmetric Acetalization
  作者：Ji Hye Kim、Ilija Čorić、Chiara Palumbo、Benjamin List

  DOI：10.1021/ja512481d

  日期：2015.2.11

  A highly enantioselective kinetic resolution of diols via asymmetric acetalization has been achieved using a chiral confined imidodiphosphoric acid catalyst. The reaction is highly efficient for the resolution of tertiary alcohols, giving selectivity factors of up to >300. Remarkably, even in cases where the selectivity factors are only moderate, highly enantioenriched diols are obtained via a stereodivergent

  使用手性限制的亚氨基二磷酸催化剂，通过不对称缩醛化实现了二醇的高度对映选择性动力学拆分。该反应对叔醇的拆分非常有效，选择性因子高达 >300。值得注意的是，即使在选择性因素仅为中等的情况下，高度对映体丰富的二醇也是通过立体发散拆分非对映缩醛获得的。