5-phenyl-2-(thiophen-2-yl)-4,5-dihydrooxazole | 1373758-33-8

• 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-phenyl-2-(thiophen-2-yl)-4,5-dihydrooxazole
• 英文别名: 5-Phenyl-2-thiophen-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 1373758-33-8
• 化学式: C₁₃H₁₁NOS
• 分子量: 229.302
• InChiKey: NBTYDTDCUPLZAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙烯 、 3-(thiophen-2-yl)-1,4,2-dioxazol-5-one 在 carbonyl(meso-tetrakis(4-tolyl)porphyrinato)ruthenium(II) 、 碘 、 copper dichloride 作用下， 以 甲苯 为溶剂， 以62%的产率得到5-phenyl-2-(thiophen-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis of 2,5-Disubstituted Oxazoles and Oxazolines Catalyzed by Ruthenium(II) Porphyrin and Simple Copper Salts

  摘要：

  A novel and moderate synthesis of 2,5-disubstituted oxazoles and oxazolines involving ruthenium(II) porphyrin copper chloride catalyzed cyclization was developed. These reactions using readily available benzene carboxylic acids and phenylethenes or phenylacetylenes are performed under mild conditions. The reactions proceed in series, giving rise to the formation of an intermolecular C-N bond and an intramolecular C-O bond, which yield oxazole or oxazoline derivatives simultaneously.

  DOI：

  10.1021/jo202663n

文献信息

• A facile preparation of various N-heterocycles using amides and olefins
  作者：Synthia S. Gratia、Edward S. Vigneau、Sumiea Eltayeb、Kishan Patel、Terence J. Meyerhoefer、Sonia Kershaw、Victor Huang、Michael De Castro

  DOI：10.1016/j.tetlet.2013.11.054

  日期：2014.1

  one pot approach for the synthesis of various nitrogen containing heterocycles including: oxazolines, thiazolines, and dihydro dioxazines via the addition of amides to olefins in the presence of N-iodosuccinimide (NIS) and propionitrile at high temperatures. Thus, the reaction of aryl/heteroaryl amides, thioamides, N-hydroxybenzamide, and phenylurea with various olefins in the presence of NIS and propionitrile

  我们在本文中报道了在高温下在N-碘代琥珀酰亚胺（NIS）和丙腈的存在下通过将酰胺加成到烯烃中来合成各种含氮杂环的一锅法，这些杂环包括：恶唑啉，噻唑啉和二氢二恶嗪。因此，在NIS和丙腈的存在下，芳基/杂芳基酰胺，硫代酰胺，N-羟基苯甲酰胺和苯基脲与各种烯烃的反应在45°C下以良好至中等的产率提供了N-杂环。的缺电子反应三ø乙酰基d -glucal和三ö乙酰基dβ-半乳糖与苯甲酰胺和噻吩-2-羧酰胺的收率很好。测试了新制备的杂环抗各种酶的能力。仅3,6-二苯基-二氢-1,4,2-二恶嗪（1c）被发现可适度抑制己糖激酶II（hHK2）。
• Chiral Hypervalent Iodine Catalysis Enables an Unusual Regiodivergent Intermolecular Olefin Aminooxygenation
  作者：Fan Wu、Navdeep Kaur、Nur-E Alom、Wei Li

  DOI：10.1021/jacsau.1c00103

  日期：2021.6.28

  strategy is described here. Amide is used as the O- and N- source to probe for regiocontrol strategies. Notably, simple additives can be selectively introduced to achieve regiodivergent oxyamination processes for electronically activated alkenes while being regio-complementary for unactivated alkenes. Our preliminary data demonstrates that this regiocontrol strategy based on nucleophile can also be applied

  本文描述了一种新型碘化物催化分子间氨氧化策略。酰胺用作 O 源和 N 源来探测区域控制策略。值得注意的是，可以选择性地引入简单的添加剂，以实现电子活化烯烃的区域发散的氧胺化过程，同时对未活化的烯烃进行区域互补。我们的初步数据表明，这种基于亲核试剂的区域控制策略也可以应用于使用手性高价碘催化的不对称过程。
• Synthesis of 2,5-Disubstituted Oxazoles and Oxazolines Catalyzed by Ruthenium(II) Porphyrin and Simple Copper Salts
  作者：Chuan Long Zhong、Bo Yang Tang、Ping Yin、Yue Chen、Ling He

  DOI：10.1021/jo202663n

  日期：2012.5.4

  A novel and moderate synthesis of 2,5-disubstituted oxazoles and oxazolines involving ruthenium(II) porphyrin copper chloride catalyzed cyclization was developed. These reactions using readily available benzene carboxylic acids and phenylethenes or phenylacetylenes are performed under mild conditions. The reactions proceed in series, giving rise to the formation of an intermolecular C-N bond and an intramolecular C-O bond, which yield oxazole or oxazoline derivatives simultaneously.