2-methyl-5-(4-methylphenyl)-1,3-oxazole | 68395-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-5-(4-methylphenyl)-1,3-oxazole
• 英文别名: 2-methyl-5-(4'-methylphenyl)oxazole；2-methyl-5-(4-methylphenyl)oxazole；2-methyl-5-(p-tolyl)oxazole；2-methyl-5-p-tolyl-oxazole；2-Methyl-5-p-tolyl-oxazol
• CAS: 68395-78-8
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: TUJNUAINMWCGSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(4-methylphenyl)-1,3-oxazole 在 氯磺酸 、 氯化亚砜 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 2-Methyl-5-(2-methyl-1,3-oxazol-5-yl)benzenesulfonyl chloride
  参考文献：
  名称：

  Probing the ‘bipolar’ nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms

  摘要：

  A series of potent inhibitors of human carbonic anhydrase (CA) isoforms I and II has been prepared via a direct, chemoselective sulfochlorination of a range of 1,3-oxazolyl benzenes and thiophenes, followed by primary sulfonamide synthesis. The latter functionality is a known zinc-binding group (ZBG) responsible for anchoring the inhibitors to the CA's zinc metal ion. The compound's periphery as well as the overall scaffold geometry was designed to enable optimal interactions with the two distinct sides of the enzyme's active site, one of which is lined with hydrophobic residues and while the other is predominantly hydrophilic. As a result, several compounds inhibiting the therapeutically important cytosolic CA I and CA II in picomolar range have been identified. These compounds are one of the most potent CA inhibitors identified to-date. Not only the remarkable (>10 000-fold), cytosolic CA I and CA II selectivity vs. the membrane-bound CA IX and CA XII isoforms, but also the pronounced CA II/I selectivity observed in some cases, allow considering this series as a set of isoform-selective chemical biology tools and promising starting points for drug candidate development. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.022
• 作为产物：
  描述：

  2-叠氮基-1-(4-甲基苯基)乙酮 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 环己烷 为溶剂， 反应 25.0h， 生成 2-methyl-5-(4-methylphenyl)-1,3-oxazole
  参考文献：
  名称：

  Synthesis of novel carbo- and heteropolycycles. 12. A new versatile synthesis of oxazoles by intramolecular aza-Wittig reaction

  摘要：

  DOI：

  10.1021/jo00263a033

文献信息

• THE BF₃-CATALYZED DECOMPOSITION OF DIAZO CARBONYL COMPOUNDS IN NITRILES. FORMATION OF ENAMIDES
  作者：Toshikazu Ibata、Masahiko Yamamoto

  DOI：10.1246/cl.1981.161

  日期：1981.2.5

  The BF3-catalyzed decomposition of α-diazoacetopheones in acetonitrile, propionitrile, or methyl thiocyanate in the presence of 1,3,5-trimethoxybenzene produced enamides (7) in good yield.

  在 1,3,5-三甲氧基苯存在下，α-重氮苯乙酮在乙腈、丙腈或甲基硫氰酸酯中的 BF3 催化分解以良好的收率生成烯酰胺 (7)。
• Synthesis and Catalytic Use of Gold(I) Complexes Containing a Hemilabile Phosphanylferrocene Nitrile Donor
  作者：Karel Škoch、Ivana Císařová、Petr Štěpnička

  DOI：10.1002/chem.201502968

  日期：2015.11.2

  [Au(1‐κP)2][SbF6]. The particular combination of a firmly coordinated (phosphane) and a dissociable (nitrile) donor moieties renders complexes 3/3′ attractive for catalysis because they can serve as shelf‐stable precursors of coordinatively unsaturated AuI fragments, analogous to those that result from the widely used [Au(PR3)(RCN)]X catalysts. The catalytic properties of the Au‐1 complexes were evaluated in model

  从[AUCL（氯化物配体的去除1个-κ P）]（2含有P-1单齿'） - （二苯基膦基）-1- cyanoferrocene配体（1），通过使用银（I）盐，得到阳离子络合物类型[Au（1）] X的类型，以环状二聚体[Au（1）] 2 X 2（3 a，X = SbF 6；3 c，X = NTf 2）或线性配位聚合物[Au（1） ] n X n（3 a'，X = SbF 6 ; 3 b'，X = ClO 4），取决于阴离子X和分离步骤。所证明为3' ，该聚合物可容易地通过加入给体，如Cl的裂解- ，四氢噻吩（THT）或1，从而产生母体化合物2，[金（THT）（1个-κ P） ] [的SbF 6 ]（5）或[AU（1个-κ P）2 ] [的SbF 6 ]（4），分别，其中最后两个化合物也可以通过在[金逐步置换THT的制备（1 ‐κ P）2 ] [SbF 6]。牢固配位的（膦）和可解离的（腈）供体
• Iron‐Promoted Practical One‐Pot Synthesis of 2,5‐Disubstituted Oxazoles
  作者：Songhui Chen、Donghu Bai、Feng Shi、Jian Li、Chunju Li、Xueshun Jia

  DOI：10.1002/cjoc.201100683

  日期：2012.7

  A practical one‐pot protocol for the synthesis of 2,5‐disubstituted oxazoles from 1‐aryl‐2‐nitroethanones was reported. In the presence of iron/AcOH in acetonitrile, the reaction of 1‐aryl‐2‐nitroethanones with trimethyl orthoacetate or trimethyl orthobenzoate delivered the corresponding 2,5‐disubstituted oxazoles in moderate to good yields.

  据报道，有一个实用的一锅法从1-芳基-2-硝基乙酮合成2，5-二取代的恶唑。在乙腈中存在铁/ AcOH时，1-芳基-2-硝基乙酮与原乙酸三甲酯或原苯甲酸三甲酯的反应以中等至良好的产率生成了相应的2,5-二取代的恶唑。
• Iodoarene-Mediated One-Pot Preparation of 2,4,5-Trisubstituted Oxazoles from Ketones
  作者：Hideo Togo、Yuhta Kawano

  DOI：10.1055/s-2007-1000871

  日期：2008.1

  2-Methyl-5-aryloxazole and 2-ethyl-5-aryloxazole derivatives were smoothly and efficiently obtained in one-pot manner from alkyl aryl ketones with iodoarene, m-chloroperbenzoic acid, and trifluoromethanesulfonic acid in acetonitrile and propionitrile, respectively. In these reactions, iodoarene works as a catalyst.

  2-甲基-5-芳基恶唑和2-乙基-5-芳基恶唑衍生物分别在乙腈和丙腈中以烷基芳基酮与碘芳烃、间氯过苯甲酸和三氟甲磺酸为原料，通过一锅法顺利高效地获得。在这些反应中，碘芳烃起到催化剂的作用。
• Iodoarene-catalyzed one-pot preparation of 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with mCPBA in nitriles
  作者：Yuhta Kawano、Hideo Togo

  DOI：10.1016/j.tet.2009.05.003

  日期：2009.8

  aryliodonium I(III) species reacts with alkyl aryl ketone to form β-keto aryliodonium species. This in turn, reacts with nitrile to form the corresponding oxazole. Iodoarene works as a catalyst. However, one equivalent of iodoarene is required because one equivalent of reactive aryliodonium I(III) species must be formed prior to the reaction with alkyl aryl ketone. Then, by introducing an ionic liquid

  2,4,5-三取代的恶唑类可以在中等的收率由烷基芳基酮，iodoarene的反应容易地制备，中号氯过苯甲酸，并在乙腈，丙腈，丁腈三氟甲磺酸，和异丁腈，分别。在这里，反应性芳基碘鎓I（III）物种是通过碘芳烃与m的反应原位形成的CPBA和三氟甲磺酸与形成的芳基碘鎓I（III）物种与烷基芳基酮反应形成β-酮基芳基碘鎓物种。这又与腈反应形成相应的恶唑。碘芳烃起催化剂的作用。然而，需要一当量的碘芳烃，因为必须在与烷基芳基酮反应之前形成一当量的反应性芳基碘鎓I（III）。然后，通过将离子液体基团引入碘代芳烃中，形成离子液体负载的碘代芳烃，可简化恶唑的分离过程。向反应混合物中加入乙酸乙酯，用NaHCO 3水溶液洗涤反应混合物。，除去乙酸乙酯并用醚萃取残留物可提供中等纯度的恶唑，残留的离子液体负载的碘芳烃可在同一反应中重复使用。