5-methyl-2-(p-tolyl)oxazol-4(5H)-one | 1393357-17-9

• 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: 5-methyl-2-(p-tolyl)oxazol-4(5H)-one
• CAS: 1393357-17-9
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: HDZDLOISUDPDFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(p-tolyl)oxazol-4(5H)-one 、 3-[2-(4-nitrophenyl)ethenyl]cyclohex-2-en-1-one 在 C₂₁H₂₈N₂ 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以83%的产率得到(R)-5-methyl-5-((S)-1-(4-nitrophenyl)-2-(3-oxocyclohex-1-enyl)ethyl)-2-p-tolyloxazol-4(5H)-one
  参考文献：
  名称：

  通过前手性碳亲核剂催化不对称的1,6-共轭加成至环状二烯酮来远程构建手性三级和四级手性中心

  摘要：

  通过将前手性碳亲核试剂催化不对称1,6-共轭加成到环状二烯酮上，已开发出前所未有的远程手性邻三级和四级中心结构。发现5 H-恶唑-4-酮和2-羟吲哚在该反应中都是非常有效的碳亲核试剂，使产物具有优异的对映异构和非对映异构选择性（ee高达99％  ee，dr> 19：1 dr 5 H-恶唑-4-和2-吲哚类化合物的ee最高为97％  ee和> 19：1 dr）。

  DOI：

  10.1002/chem.201503530

文献信息

• Highly Stereoselective Synthesis of α-Alkyl-α-Hydroxycarboxylic Acid Derivatives Catalyzed by a Dinuclear Zinc Complex
  作者：Barry M. Trost、Keiichi Hirano

  DOI：10.1002/anie.201201116

  日期：2012.6.25

  dinuclear zinc–ProPhenol catalyst enables highly enantioselective nitro‐Michael reactions with oxazol‐4(5H)‐ones as nucleophilic substrates (see scheme, Nap=2‐naphthyl). This work highlights the utility of the ProPhenol family of ligands. The modular nature of these ligands proved crucial in the optimization of reaction conditions to achieve excellent stereoselectivities.

  双核锌-ProPhenol催化剂可与作为亲核底物的恶唑-4（5 H）-酮进行高度对映选择性的硝基-迈克尔反应（请参阅方案，Nap = 2-萘基）。这项工作突出了ProPhenol配体家族的实用性。这些配体的模块性质被证明对于优化反应条件以实现出色的立体选择性至关重要。
• Highly enantioselective allylic alkylation of 5 H -oxazol-4-ones with Morita-Baylis-Hillman carbonates
  作者：Han Xu、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tet.2018.06.055

  日期：2018.8

  An organocatalytic enantioselective allylic alkylation of 5H-oxazol-4-ones with Morita-Baylis-Hillman carbonates has been developed. With 10 mol% of commercially available cinchonidine, a wide range of substituted 5H-oxazol-4-one derivatives were constructed in good-to-excellent yields with high diastereo- and enantioselectivities. The allylic alkylation adducts obtained are valuable precursors for

  已经开发了用Morita-Baylis-Hillman碳酸盐对5 H-恶唑-4-酮进行有机催化对映选择性烯丙基烷基化反应。用10 mol％的市售可可宁定，以良好至优异的产率以及高的非对映选择性和对映选择性，构建了范围广泛的取代的5 H-恶唑-4-酮衍生物。获得的烯丙基烷基化加合物是用于合成手性α-烷基α-羟基羧酸衍生物的有价值的前体，其代表许多生物活性化合物中的一系列通用结构单元。
• Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5<i>H</i>-oxazol-4-ones with <i>N</i>-Maleimides
  作者：Shuai Qiu、Richmond Lee、Bo Zhu、Michelle L. Coote、Xiaowei Zhao、Zhiyong Jiang

  DOI：10.1021/acs.joc.6b01451

  日期：2016.9.2

  An organocatalytic asymmetric reaction between 5H-oxazol-4-ones and N-substituted maleimides is disclosed. Employing Takemoto's chiral tertiary amine-thiourea as the catalyst, [4 + 2] annulation reactions were performed with high chemoselectivity, leading to a series of biologically important chiral oxo-bridged piperidone-fused succinimides in good to excellent enantioselectivities (up to >99% ee) and >19:1 dr.
• Organocatalytic Asymmetric Michael Addition of 5<i>H</i>-Oxazol-4-ones to Nitroolefins
  作者：Baokun Qiao、Yongqiang An、Qian Liu、Wenguo Yang、Hongjun Liu、Juan Shen、Lin Yan、Zhiyong Jiang

  DOI：10.1021/ol401062z

  日期：2013.5.17

  The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral alpha-alkyl-alpha-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.
• Highly enantioselective α-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides
  作者：Mei Xu、Baokun Qiao、Shaobo Duan、Hongjun Liu、Zhiyong Jiang

  DOI：10.1016/j.tet.2014.09.037

  日期：2014.11

  An unprecedented asymmetric alpha-sulfenylation of 5H-oxazol-4-ones to N-(sulfanyl)succinimides has been established, to access various alpha-sulfenylated adducts with good to excellent enantioselectivities (86-95% ee) by utilizing a cinchona alkaloid-derived squaramide as catalyst. The conditions of this alpha-sulfenylation protocol simultaneously satisfy N-(arylthio)succinimides, N-(benzylthio)succinimides, and N-(alkylthio)succinimides by tuning the substituted groups of 5H-oxazol-4-ones on the 2-position as well as additives. (C) 2014 Elsevier Ltd. All rights reserved.