(+/-)-1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diol | 354153-47-2

• 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: (+/-)-1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diol
• 英文别名: 1-mesitylethane-1,2-diol；1-(2,4,6-Trimethylphenyl)ethane-1,2-diol
• CAS: 354153-47-2
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: JXHICCPIVYTCHE-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  341.9±37.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (+/-)-1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diol 在 三氟甲磺酸 、 乙腈 作用下， 以59%的产率得到(+/-)-2-amino-2-(2,4,6-trimethylphenyl)ethanol
  参考文献：
  名称：

  An Effective and Useful Synthesis of Enantiomerically Enriched Arylglycinols

  摘要：

  DOI：

  10.1002/1099-0690(200105)2001:10<1937::aid-ejoc1937>3.3.co;2-u
• 作为产物：
  描述：

  2,4,6-三甲基苯乙烯 在 奎宁环 、 四氧化锇 、 叔丁醇 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 (+/-)-1-(2,4,6-trimethyl-phenyl)-ethane-1,2-diol
  参考文献：
  名称：

  Burgess试剂在化学合成中的新用途：氨基磺酸盐，糖胺和磺酰胺的简便和立体选择性形成方法。

  摘要：

  尽管Burgess试剂（甲氧基羰基氨磺酰基三乙铵氢氧化物，内盐）已发现在化学合成中作为脱水剂具有重要用途，但几乎没有工作针对其在其他合成应用中的潜力。正如本文将要详细介绍的那样，我们发现，将Burgess试剂应用于适当的底物上，例如从1,2-二醇或环氧醇，α-和C-形成氨基磺酸盐时，在完成许多非脱水合成任务方面非常有效。来自碳水化合物的β-糖胺和来自1,2-氨基醇的环状磺酰胺 除了描述这些新反应歧管的功能之外，我们还描述了一组替代的Burgess型试剂的构造，这些试剂进一步扩展了这些新反应的范围。

  DOI：

  10.1002/chem.200400503

文献信息

• Iodine-Initiated Dioxygenation of Aryl Alkenes Using<i>tert</i>-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides
  作者：Xiaofang Gao、Jiani Lin、Li Zhang、Xinyao Lou、Guanghui Guo、Na Peng、Huan Xu、Yi Liu

  DOI：10.1021/acs.joc.1c01968

  日期：2021.11.5

  An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived

  以碘为催化剂，叔丁基氢过氧化物 (TBHPs) 为氧化剂，在水中开发了一种环保高效的芳基烯烃双氧化反应，用于构建邻二醇。该协议高效、可持续且操作简单。详细的机理研究表明，其中一个羟基来自水，另一个来自 TBHP。此外，以碘为催化剂，Na 2 CO 3为添加剂，碳酸亚丙酯为溶剂，可以以良好的收率获得双过氧化物。
• Acid-Assisted Ru-Catalyzed Enantioselective Amination of 1,2-Diols through Borrowing Hydrogen
  作者：Li-Cheng Yang、Ya-Nong Wang、Yao Zhang、Yu Zhao

  DOI：10.1021/acscatal.6b02959

  日期：2017.1.6

  Here, we present a highly enantioselective synthesis of 1,2-amino alcohols from readily available racemic 1,2-diols through a borrowing hydrogen process. An intriguing acid effect was discovered for this Ru-catalyzed amination reaction, which led to a significant improvement of the stereoselectivity of the process. Preliminary mechanistic studies suggest a scenario of Brønsted acid-assisted dynamic

  在这里，我们介绍了通过借用氢过程从容易获得的外消旋1,2-二醇中高度对映选择性合成1,2-氨基醇的方法。对于这种Ru催化的胺化反应，发现了一种引人入胜的酸效应，这导致了该方法的立体选择性的显着改善。初步的机理研究表明，布朗斯台德酸辅助的醇动力学动力学不对称胺化的情况。
• Electrochemical ring-opening carboxylation of cyclic carbonate with carbon dioxide
  作者：Li Tao、He Wang、Xiao-Fei Liu、Wei-Min Ren、Xiao-Bing Lu、Wen-Zhen Zhang

  DOI：10.1039/d4cc01695e

  日期：——

  ring-opening carboxylation of styrene carbonates with CO2 to achieve dicarboxylic acids and/or β-hydroxy acids has been developed via the selective cleavage of the C(sp3)–O bond in cyclic carbonates. The product selectivity is probably determined by the stability and reactivity of the key benzylic radical and carbanion intermediate.

  通过选择性裂解环状碳酸酯中的 C(sp 3 )–O 键，开发了苯乙烯碳酸酯与 CO 2的电还原开环羧化以获得二羧酸和/或β-羟基酸。产物选择性可能由关键的苄基和碳负离子中间体的稳定性和反应性决定。
• Metal-Free Dihydroxylation of Alkenes using Cyclobutane Malonoyl Peroxide
  作者：Kevin M. Jones、Nicholas C. O. Tomkinson

  DOI：10.1021/jo202084w

  日期：2012.1.20

  Cyclobutane malonoyl peroxide (7), prepared in a single step from the commercially available diacid 6, is an effective reagent for the dihydroxylation of alkenes. Reaction of a chloroform solution of 7 with an alkene in the presence of I equiv of water at 40 degrees C followed by alkaline hydrolysis leads to the corresponding diol (30-84%). With 1,2-disubstituted alkenes, the reaction proceeds with syn-selectivity (3:1 -> 50:1). A mechanism consistent with experimental findings is proposed, which is supported by deuterium and oxygen labeling studies and explains the stereoselectivity observed. Alternative reaction pathways that are dependent on the structure of the starting alkene are also described leading to the synthesis of allylic alcohols and gamma-lactones.
• Alkene Syn Dihydroxylation with Malonoyl Peroxides
  作者：James C. Griffith、Kevin M. Jones、Sylvain Picon、Michael J. Rawling、Benson M. Kariuki、Matthew Campbell、Nicholas C. O. Tomkinson

  DOI：10.1021/ja1066674

  日期：2010.10.20

  Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 degrees C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to > 50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.