4,4-dimethyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole | 42407-05-6

• 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: 4,4-dimethyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole
• 英文别名: 4,4-dimethyl-2-(4-nitrophenyl)-4,5-dihydrooxazole；4,4-dimethyl-2-(4-nitrophenyl)-5H-1,3-oxazole
• CAS: 42407-05-6
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: XYFBYFUMLQSBIH-UHFFFAOYSA-N

物化性质

• 熔点：
  96.5-99 °C(Solv: ligroine (8032-32-4); dichloromethane (75-09-2))
• 沸点：
  345.7±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole 在 三乙胺 作用下， 以 环己烷 为溶剂， 反应 3.0h， 生成 dichloro-[3-dichloroacetyl-4,4-dimethyl-2-(4-nitro-phenyl)-oxazolidin-2-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Addition of dichloroketene to 2-aryl-.DELTA.2-oxazolines

  摘要：

  DOI：

  10.1021/jo00965a029
• 作为产物：
  描述：

  N-hydroxy-N-(1,1-dimethylethyl)-4-nitrobenzamide 在 吡啶 、 对甲苯磺酰氯 作用下， 生成 4,4-dimethyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Sulfonic Acid Esters as Alkylating Agents: Formation of 2-Oxazolines¹

  摘要：

  DOI：

  10.1021/ja01119a033

文献信息

• Silicon-rhodamine isothiocyanate for fluorescent labelling
  作者：Veselin Nasufović、Patrick Then、Fabian Dröge、Michael Duong、Christoph Kaether、Benjamin Dietzek、Rainer Heintzmann、Hans-Dieter Arndt

  DOI：10.1039/d0ob02016h

  日期：——

  An efficient synthesis for silicon-rhodamines was developed, enabling the preparation and evaluation of silicon-rhodamine isothiocyanate (SITC) as a novel tool for facile fluorescent labeling. Ease of use in conjugation to amino groups, high stability and excellent photophysical properties are demonstrated. SITC-actin was found to be neutral to F-actin polymerization induction and well suited for high

  开发了一种有效的合成方法，可用于制备和评估异硫氰酸硅罗丹明（SITC），将其作为简便的荧光标记新工具。易于与氨基结合使用，具有高稳定性和出色的光物理性质。发现SITC-肌动蛋白对F-肌动蛋白聚合诱导是中性的，并且非常适合于高分辨率荧光显微术。
• Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions
  作者：B.P Bandgar、S.S Pandit

  DOI：10.1016/s0040-4039(03)00251-x

  日期：2003.3

  2-Acyloxy-4,6-dimethoxy-1,3,5-triazines obtained from carboxylic acids and 2-chloro-4,6-dimethoxy-1,3,5-triazine were subsequently treated with 2-amino-2-methyl-1-propanol to afford the corresponding 2-oxazolines in excellent yield at room temperature.

  随后将由羧酸获得的2-酰氧基-4,6-二甲氧基-1,3,5-三嗪和2-氯-4,6-二甲氧基-1,3,5-三嗪用2-氨基-2-甲基处理-1-丙醇在室温下以优异的收率得到相应的2-恶唑啉。
• Facile Syntheses of Oxazolines and Thiazolines with <i>N</i>-Acylbenzotriazoles under Microwave Irradiation
  作者：Alan R. Katritzky、Chunming Cai、Kazuyuki Suzuki、Sandeep K. Singh

  DOI：10.1021/jo0355092

  日期：2004.2.1

  Microwave reactions of 2-amino-2-methyl-1-propanol (2) or 2-aminoethanethiol hydrochloride (4) with readily available N-acylbenzotriazoles 1a−j in the presence of SOCl2 produced 2-substituted 2-oxazolines 3a−j in 84−98% yields and 2-substituted thiazolines 5a−i in 85−97% yields, respectively. With use of this method chiral oxazoline 6, bisoxazoline 7, bisthiazoline 8, and 5,6-dihydro-4H-1,3-oxazines

  在SOCl 2的存在下，2-氨基-2-甲基-1-丙醇（2）或2-氨基乙硫醇盐酸盐（4）与易于获得的N-酰基苯并三唑1a - j的微波反应产生了2-取代的2-恶唑啉3a - j分别以84-98％的产率和2-取代的噻唑啉5a - i的产率为85-97％。使用该方法时，手性恶唑啉6，双恶唑啉7，双噻唑啉8和5,6-二氢-4 H -1,3-恶嗪9或10还制备了82-96％的产率。这些结果证明了N-酰基苯并三唑在温和条件下和微波辐射下反应时间短的情况下在恶唑啉和噻唑啉制备中的新应用。
• An Efficient, Eco-Friendly, One-Pot Protocol for the Synthesis of 2-Oxazolines Promoted by Ionic Liquid/Indium Chloride
  作者：R. Kamakshi、Boreddy S. R. Reddy

  DOI：10.1071/ch06061

  日期：——

  2-Oxazolines have been synthesized using a solventless ionic liquid melt in good yields at ambient temperatures. The efficiency of various Lewis acid catalysts for the same reaction has been compared. The effectiveness of different alkyl chains in the ionic liquids for the synthesis of oxazolines has been studied and a butylmethylimidazolinium chloride/indium chloride melt has been found to be the best media for promoting the reaction.

  使用无溶剂离子液体熔体合成了 2-恶唑啉类化合物，并在常温下获得了良好的产率。比较了各种路易斯酸催化剂在相同反应中的效率。研究了离子液体中不同烷基链对合成噁唑啉的有效性，发现丁基甲基氯化咪唑啉鎓/氯化铟熔体是促进反应的最佳介质。
• Pd(OAc)2/2-aryl-2-oxazolines catalyzed Suzuki coupling reactions of aryl bromides and arylboronic acids
  作者：Bin Tao、David W Boykin

  DOI：10.1016/s0040-4039(02)00955-3

  日期：2002.7

  A series of 2-aryl-2-oxazolines were prepared and examined as ligands for the Suzuki coupling reaction of aryl bromides and arylboronic acids. 2,2′-(1,3-Phenylene)bisoxazoline/Pd(OAc)2 was found to be an efficient catalyst for a variety of substrates to afford the coupling products in good to excellent yields.

  制备了一系列2-芳基-2-恶唑啉，并作为芳基溴化物和芳基硼​​酸的Suzuki偶联反应的配体进行了检测。发现2,2'-（1,3-亚苯基）双恶唑啉/ Pd（OAc）2是多种底物的有效催化剂，以良好的产率提供了良好的偶联产物。

表征谱图