5-methyl-2-(m-tolyl)oxazol-4(5H)-one | 1393357-22-6

• 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-(m-tolyl)oxazol-4(5H)-one
• 英文别名: 5-Methyl-2-(3-methylphenyl)-1,3-oxazol-4-one
• CAS: 1393357-22-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: PWEXWUXYVPUWIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(m-tolyl)oxazol-4(5H)-one 在 4-chloro-N,N'-bis-[(S)-4-methyloxazolin-2-yl]pyridine 、 titanium(IV) isopropylate 、 噻吩-2-甲酸亚铜(I) 、 copper(I) trifluoromethanesulfonate benzene 作用下， 以 甲苯 为溶剂， 反应 49.5h， 生成 C₂₇H₂₄N₄O₄S
  参考文献：
  名称：

  Cu / Zn和Cu ​​/ Ti催化实现5H-噻唑-4-酮和5H-恶唑-4-酮的非对映和对映选择性炔丙基化

  摘要：

  报道为5不对称炔丙基取代（APS）反应ħ使用铜/锌双金属催化体系和5中的APS反应-噻唑-4-酮ħ使用Cu / Ti的催化体系-恶唑-4-酮。这些反应提供了具有两个邻位立体中心的高功能基团，末端炔烃含量高的产品，并具有良好至优异的非对映和对映选择性。这项研究表明，使用双金属催化体系作为一种可行的方法来改善铜催化的APS反应的选择性。

  DOI：

  10.1002/anie.201809391
• 作为产物：
  描述：

  间甲苯乙酰胺 在 吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲基叔丁基醚 为溶剂， 反应 5.0h， 生成 5-methyl-2-(m-tolyl)oxazol-4(5H)-one
  参考文献：
  名称：

  双核锌配合物催化的α-烷基-α-羟基羧酸衍生物的高立体选择性合成

  摘要：

  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。

  DOI：

  10.1002/anie.201201116

文献信息

• 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。
• Chemoselective Switch in the Asymmetric Organocatalysis of 5<i>H</i>-Oxazol-4-ones and<i>N</i>-Itaconimides: Addition-Protonation or [4+2] Cycloaddition
  作者：Bo Zhu、Richmond Lee、Jiangtao Li、Xinyi Ye、San-Ni Hong、Shuai Qiu、Michelle L. Coote、Zhiyong Jiang

  DOI：10.1002/anie.201507796

  日期：2016.1.22

  We report a synthetic strategy for a chemoselective switch and a diastereo‐divergent approach for the asymmetric reaction of 5H‐oxazol‐4‐ones and N‐itaconimides catalyzed by l‐tert‐leucine‐derived tertiary amine–urea compounds. The reaction was modulated to harness either tandem conjugate addition–protonation or [4+2] cycloaddition as major product with excellent enantio‐ and diastereoselectivities

  我们报告的化学选择性开关和用于5不对称反应中的非对映发散方法合成策略ħ -恶唑-4-酮和Ñ -itaconimides催化升-叔亮氨酸衍生的叔胺-尿素化合物。调节反应以利用串联共轭加成-质子化或[4 + 2]环加成为主要产物，具有出色的对映异构和非对映异构选择性。将对映体富集的环加成产物置于碱性硅胶试剂中，与在加成质子化条件下直接获得的产物相比，可生成非对映异构体，从而开辟了非对映异构路线，从而形成了1,3-叔-叔-季铵盐立体中心。量子化学研究进一步为[4 + 2]过程提供了立体化学分析，并提出了这种化学选择性开关的合理机制。
• 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.