2-(m-tolyl)propane-1,2-diol

• 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-(m-tolyl)propane-1,2-diol
• 英文别名: 2-(3-Methylphenyl)propane-1,2-diol；2-(3-methylphenyl)propane-1,2-diol
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: FNULQZCMIWNUHA-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

反应信息

• 作为反应物：
  描述：

  2-(m-tolyl)propane-1,2-diol 、 异戊醛 在 磷酸二苯酯 作用下， 以 甲苯 为溶剂， 生成 (2S,4R)-2-isobutyl-4-methyl-4-m-tolyl-1,3-dioxolane
  参考文献：
  名称：

  通过催化不对称缩醛化拆分二醇

  摘要：

  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。

  DOI：

  10.1021/ja512481d
• 作为产物：
  描述：

  2-(m-tolyl)propanal 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-(m-tolyl)propane-1,2-diol
  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

• Visible light-promoted dihydroxylation of styrenes with water and dioxygen
  作者：Bo Yang、Zhan Lu

  DOI：10.1039/c7cc06745c

  日期：——

  The first efficient visible light promoted metal-free dihydroxylation of styrenes with water and dioxygen has been developed for the construction of vicinal alcohols. The protocol was operationally simple with broad substrate scope. The mechanistic studies demonstrated that one of the hydroxyl group came from water and the other one came from molecular oxygen. Additionally, the ß-alkyoxy alcohols could

  已经开发出第一种有效的可见光促进苯乙烯与水和双氧的无金属二羟基化反应，用于邻位醇的构建。该协议操作简单，具有广泛的底物范围。机理研究表明，一个羟基来自水，另一个羟基来自分子氧。另外，还可以使用类似的策略获得β-烷氧基醇。
• Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis
  作者：Martin Pawliczek、Takuya Hashimoto、Keiji Maruoka

  DOI：10.1039/c7sc04854h

  日期：——

  Herein, we report the first alkylative kinetic resolution of vicinal alcohols realized by cooperative use of a chiral quaternary ammonium salt and an achiral borinic acid. In addition, a catalytic regioselective alkylation of a secondary alcohol in the presence of an unprotected primary one is presented, emphasizing the unique selectivity and potential of this ammonium borinate catalysis.

  在此，我们报告了通过手性季铵盐和非手性硼酸的协同使用实现的连位醇的第一次烷基化动力学拆分。此外，还介绍了在未保护的伯醇存在下仲醇的催化区域选择性烷基化，强调了这种硼酸铵催化的独特选择性和潜力。
• A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes
  作者：Michael R. Witten、Eric N. Jacobsen

  DOI：10.1021/acs.orglett.5b01193

  日期：2015.6.5

  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.
• 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。