2-(3-Chlorophenyl)-5-methyl-1,3-oxazol-4-one | 1426339-57-2

• 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: 2-(3-Chlorophenyl)-5-methyl-1,3-oxazol-4-one
• 英文别名: 2-(3-chlorophenyl)-5-methyl-1,3-oxazol-4-one
• CAS: 1426339-57-2
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: ODLNCTSPLJODHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  β-硝基苯乙烯 、 2-(3-Chlorophenyl)-5-methyl-1,3-oxazol-4-one 在 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(3,3-dimethyl-1-(piperidin-1-yl)butan-2-yl)thiourea 作用下， 以 甲基叔丁基醚 为溶剂， 反应 40.5h， 以93%的产率得到(S)-2-(3-chlorophenyl)-5-methyl-5-((S)-2-nitro-1-phenylethyl)oxazol-4(5H)-one
  参考文献：
  名称：

  Organocatalytic Asymmetric Michael Addition of 5H-Oxazol-4-ones to Nitroolefins

  摘要：

  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.

  DOI：

  10.1021/ol401062z

文献信息

• Chiral Guanidine-catalyzed 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones to Alkynones
  作者：Tomonori Misaki、Nari Jin、Kei Kawano、Takashi Sugimura

  DOI：10.1246/cl.2012.1675

  日期：2012.12.5

  An asymmetric 1,4-addition reaction of 5H-oxazol-4-ones to alkynones using chiral guanidine catalysts bearing a hydroxy group at the appropriate position was developed, and applied to several substrates. The method provides a synthetically useful enone-substituted α-hydroxy acid derivatives with a chiral quaternary α-carbon atom.

  使用在适当位置带有羟基的手性胍催化剂，开发了 5H-恶唑-4-酮与炔酮的不对称 1,4-加成反应，并将其应用于多种底物。该方法提供了合成上有用的具有手性季α-碳原子的烯酮取代的α-羟基酸衍生物。
• Stereoconvergent 1,4-Addition Reaction of 5<i>H</i> -Oxazol-4-ones with <i>E</i> ,<i>Z</i> Isomeric Mixture of Alkylidene β-Ketoesters Catalyzed by Chiral Guanidines
  作者：Tomonori Misaki、Toshifumi Tatsumi、Tatsumasa Okamoto、Yusuke Hayashi、Nari Jin、Takashi Sugimura

  DOI：10.1002/chem.201802271

  日期：2018.7.11

  A 1,4‐addition reaction of 5H‐oxazol‐4‐ones to alkylidene β‐ketoesters, which was catalyzed by using chiral guanidines via a dynamic kinetic resolution process that involved geometric isomerization of the alkylidene β‐ketoesters, was developed. This method allowed using E,Z isomeric mixture of various acyclic alkylidene β‐ketoesters to obtain the products stereoselectively. The relation between the

  开发了5 H-恶唑-4-酮与亚烷基β-酮酸酯的1,4加成反应，该反应是通过使用手性胍通过动态动力学拆分过程催化的，该过程涉及亚烷基β-酮酸酯的几何异构化。该方法允许使用各种无环亚烷基β-酮酸酯的E，Z异构体混合物立体选择性地获得产物。研究了产物的几何形状与立体选择性之间的关系，并对产物进行了衍生化为相应的α-酰基-γ-内酯。
• 1,4-Addition Reaction of 5<i>H</i>-Oxazol-4-ones to Allenic Esters and Ketones Catalyzed by Chiral Guanidines
  作者：Nari Jin、Tomonori Misaki、Takashi Sugimura

  DOI：10.1246/cl.130295

  日期：2013.8.5

  In this paper, a chiral guanidine-catalyzed 1,4-addition reaction of 5H-oxazol-4-ones to allenic esters and ketones is described. 5H-Oxazol-4-ones substituted with a 2-chlorophenyl group were suitable pronucleophiles that gave high enantioselectivities. Subsequent hydrolysis of the obtained adduct gave the corresponding γ-butenolide ester without loss of enantiopurity and was transformed into (+)-crobarbatic acid in a few steps.

  本文介绍了手性胍催化的 5H-oxazol-4-ones 与异烯酯和酮的 1,4 加成反应。用 2-氯苯基取代的 5H-恶唑-4-酮是合适的代核物，具有很高的对映选择性。随后对获得的加合物进行水解，可得到相应的γ-丁烯内酯，且不失对映纯度，并在几个步骤中转化为(+)-巴巴拉汀酸。
• 1,6-Addition Reaction of 5<i>H</i>-Oxazol-4-ones to Conjugated Dienones Catalyzed by Chiral Guanidines
  作者：Akane Morita、Tomonori Misaki、Takashi Sugimura

  DOI：10.1246/cl.140713

  日期：2014.12.5

  A chiral guanidine-catalyzed 1,6-addition reaction of 5H-oxazol-4-ones to α,β,γ,δ-diunsaturated ketones is described in this study. The addition reaction proceeded regiospecifically to yield a 1,6-addition product with high enantioselectivity. Obtained adducts of the 1,6-addition could be converted into the corresponding chiral 7-oxo-α-hydroxy acid derivatives or chiral α-homoallylic-hydroxy acid derivatives via 2nd generation Grubbs catalyst-mediated olefin metatheses.

  本研究描述了一种手性胍催化的 5H-恶唑-4-酮与α,β,γ,δ-二不饱和酮的 1,6-加成反应。加成反应以区域特异性的方式进行，生成了具有高对映体选择性的 1,6 加成产物。通过第二代 Grubbs 催化剂介导的烯烃偏析，1,6-加成反应得到的加合物可转化为相应的手性 7-氧代-α-羟基酸衍生物或手性 α-高烯丙基羟基酸衍生物。
• 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.