2-(4-bromophenyl)-5-phenyl-4,5-dihydrooxazole | 1239713-17-7

• 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-(4-bromophenyl)-5-phenyl-4,5-dihydrooxazole
• 英文别名: 2-(4-bromophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 1239713-17-7
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: OQDJHLPIKBACJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  咪唑 、 2-(4-bromophenyl)-5-phenyl-4,5-dihydrooxazole 以 醋酸异丙酯 为溶剂， 反应 24.0h， 以41%的产率得到4-bromo-N-(2-(1H-imidazol-1-yl)-2-phenylethyl)benzamide
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides

  摘要：

  A series of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides were prepared, using an efficient three-to five-step synthesis, and evaluated for their inhibitory activity against human cytochrome P450C24A1 (CYP24A1) hydroxylase. Inhibition ranged from IC50 0.3-72 mu M compared with the standard ketoconazole IC50 0.52 mu M, with the styryl derivative (11c) displaying enhanced activity (IC50 = 0.3 mu M) compared with the standard, providing a useful preliminary lead for drug development. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.011
• 作为产物：
  描述：

  C₁₆H₁₆BrNO₄S 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-bromophenyl)-5-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis and CYP24A1 inhibitory activity of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides

  摘要：

  A series of N-(2-(1H-imidazol-1-yl)-2-phenylethyl)arylamides were prepared, using an efficient three-to five-step synthesis, and evaluated for their inhibitory activity against human cytochrome P450C24A1 (CYP24A1) hydroxylase. Inhibition ranged from IC50 0.3-72 mu M compared with the standard ketoconazole IC50 0.52 mu M, with the styryl derivative (11c) displaying enhanced activity (IC50 = 0.3 mu M) compared with the standard, providing a useful preliminary lead for drug development. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.011

文献信息

• Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses <i>via</i> C_sp³–H functionalizations
  作者：Navdeep Kaur、Elizabeth C. Ziegelmeyer、Olutayo N. Farinde、Jonathon T. Truong、Michelle M. Huynh、Wei Li

  DOI：10.1039/d1cc04588a

  日期：——

  (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3–H bonds that enabled the stereoselective synthesis of cis- and trans-oxazolines.

  此处描述了催化苄基 C sp 3 –H 功能化协议。这种可见光介导的过程集中在利用溴化物催化剂和氧化剂来生成以氮 (N) 为中心的自由基，用于位点选择性氢原子转移 (HAT) 过程。这种策略使依赖酰胺身份的许多 N-杂环的非常规合成成为可能。我们还发现了 C sp 3 -H 键立体化学分化的亲核依赖性动力学分辨率，这使得顺式和反式恶唑啉的立体选择性合成成为可能。
• Visible-Light-Driven [3 + 2]/[4 + 2] Annulation Reactions of Alkenes with <i>N</i>-Aminopyridinium Salts
  作者：Yu-Zhao Wang、Peng-Yu Liang、Hong-Chao Liu、Wu-Jie Lin、Pan-Pan Zhou、Wei Yu

  DOI：10.1021/acs.orglett.2c02323

  日期：2022.8.19

  The annulation reactions of benzoamidyl radicals with alkenes were realized under visible light irradiation with fac-Ir(ppy)3 as catalyst and N-aminopyridinium salts as benzoamidyl radical precursors. The reaction can deliver two distinct types of products: in the case of vinyl arenes, [3 + 2] annulation product dihydrooxazoles were yielded exclusively; when alkyl-substituted alkenes were used, on the

  以fac -Ir(ppy) 3为催化剂，N-氨基吡啶鎓盐为苯甲酰胺自由基前体，在可见光照射下实现了苯甲酰胺自由基与烯烃的环化反应。该反应可以产生两种不同类型的产物：在乙烯基芳烃的情况下，仅产生 [3 + 2] 环化产物二氢恶唑；另一方面，当使用烷基取代的烯烃时，它提供了[4 + 2]环化产物二氢异喹啉酮。通过 DFT 计算阐明了决定反应后果的因素。
• 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。