2-(4-溴苯基)-4-恶唑甲醇 | 36841-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-溴苯基)-4-恶唑甲醇
• 英文名称: 2-(4-bromophenyl)-4-hydroxymethyloxazole
• 英文别名: [2-(4-bromo-phenyl)-oxazol-4-yl]-methanol；[2-(4-bromophenyl)-1,3-oxazol-4-yl]methanol
• CAS: 36841-48-2
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: RYNAHCKMFPVCPI-UHFFFAOYSA-N

物化性质

• 沸点：
  388.2±52.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(4-溴苯基)-4-恶唑甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(4-溴苯基)-4-(氯甲基)-1,3-恶唑
  参考文献：
  名称：

  Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB

  摘要：

  A high-throughput screening effort on 45,000 compounds resulted in the discovery of a disubstituted oxazole as a new structural class inhibitor of Mycobacterium tuberculosis (Mtb). In order to improve the activity and investigate the SAR of this scaffold, a series of disubstituted azole analogues have been designed and synthesized. The newly synthesized compounds 1a-y were evaluated for their in vitro anti-TB activity versus replicating, multi-and extensive drug resistant Mtb strains. All the compounds, except 1o, 1p and 1q, showed potent anti-TB activity with MIC of 1-64 mg/L. The test of broad spectrum panel revealed that this series are specific to Mtb. The cytotoxicity assessment indicated that the compounds were not cytotoxic against HEK 293 cells. The compounds could have a novel mechanism to anti-Mtb as they can inhibit drug sensitive and drug resistant Mtb. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.072
• 作为产物：
  描述：

  methyl 2-(4-bromophenyl)oxazole-4-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-溴苯基)-4-恶唑甲醇
  参考文献：
  名称：

  Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB

  摘要：

  A high-throughput screening effort on 45,000 compounds resulted in the discovery of a disubstituted oxazole as a new structural class inhibitor of Mycobacterium tuberculosis (Mtb). In order to improve the activity and investigate the SAR of this scaffold, a series of disubstituted azole analogues have been designed and synthesized. The newly synthesized compounds 1a-y were evaluated for their in vitro anti-TB activity versus replicating, multi-and extensive drug resistant Mtb strains. All the compounds, except 1o, 1p and 1q, showed potent anti-TB activity with MIC of 1-64 mg/L. The test of broad spectrum panel revealed that this series are specific to Mtb. The cytotoxicity assessment indicated that the compounds were not cytotoxic against HEK 293 cells. The compounds could have a novel mechanism to anti-Mtb as they can inhibit drug sensitive and drug resistant Mtb. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.072

文献信息

• Single-Step Microwave-Mediated Synthesis of Oxazoles and Thiazoles from 3-Oxetanone: A Synthetic and Computational Study
  作者：David Orr、Alexandra Tolfrey、Jonathan M. Percy、Joanna Frieman、Zoë A. Harrison、Matthew Campbell-Crawford、Vipulkumar K. Patel

  DOI：10.1002/chem.201301011

  日期：2013.7.15

  The direct microwave‐mediated condensation between 3‐oxetanone and primary amides and thioamides has delivered moderate to good yields of (hydroxymethyl)oxazoles and (hydroxymethyl)thiazoles. The reactions use a sustainable solvent and only require short reaction times. These are highly competitive methods for the construction of two classes of valuable heteroarenes, which bear a useful locus for further

  3-氧杂环丁酮与伯酰胺和硫代酰胺之间的直接微波介导缩合反应产生了中等到良好的（羟甲基）恶唑和（羟甲基）噻唑收率。反应使用可持续的溶剂，只需要很短的反应时间。这些是构建两类有价值的杂芳烃的高度竞争性方法，它们具有进一步阐明的有用位置。电子结构计算表明，事件的顺序涉及sp 3处硫属元素原子的攻击碳和烷基-氧裂解。清楚地表明了酸催化的关键作用，并证明了酸强度的重要性。计算的势垒也与所观察到的硫酰胺和酰胺反应性顺序完全一致。自发的开环涉及适度的CO裂解，减缓了应力释放的程度。在酸催化的途径上，CO的裂解仍然不太广泛，但是通过羧酸催化剂，质子转移到核反应堆中的进展非常快，而基本上是用甲磺酸完成的。
• Nitrierung und Halogenierung einiger 2-Aryl-4-chlormethyl-oxazole. XXIII. Mitt. Heterozyklische Verbindungen
  作者：I. Simiti、Elena Chindris

  DOI：10.1002/ardp.19723050706

  日期：——

  Es wird die Nitrierung und Bromierung des 2‐Aryl‐4‐chlormethyloxazols untersucht. Bei der Bromierung ist die Stellung 5 des Oxazolringes besonders reaktiv. Bei der Nitrierung wird die Nitrogruppe im Benzolring immer in ortho‐Stellung zum vorhandenen Substituenten eingeführt.

  研究了2-芳基-4-氯甲基恶唑的硝化和溴化。恶唑环的 5 位在溴化过程中特别具有反应性。在硝化过程中，苯环中的硝基总是在取代基的邻位引入。
• SIMITI I.; CHINDRIS E., ARCH. PHARM. <APBD-AJ>, 1975, 308, NO 9, 688-692
  作者：SIMITI I.、 CHINDRIS E.

  DOI：——

  日期：——
• Discovery of the disubstituted oxazole analogues as a novel class anti-tuberculotic agents against MDR- and XDR-MTB
  作者：Dongsheng Li、Nana Gao、Ningyu Zhu、Yuan Lin、Yan Li、Minghua Chen、Xuefu You、Yu Lu、Kanglin Wan、Jian-Dong Jiang、Wei Jiang、Shuyi Si

  DOI：10.1016/j.bmcl.2015.09.072

  日期：2015.11

  A high-throughput screening effort on 45,000 compounds resulted in the discovery of a disubstituted oxazole as a new structural class inhibitor of Mycobacterium tuberculosis (Mtb). In order to improve the activity and investigate the SAR of this scaffold, a series of disubstituted azole analogues have been designed and synthesized. The newly synthesized compounds 1a-y were evaluated for their in vitro anti-TB activity versus replicating, multi-and extensive drug resistant Mtb strains. All the compounds, except 1o, 1p and 1q, showed potent anti-TB activity with MIC of 1-64 mg/L. The test of broad spectrum panel revealed that this series are specific to Mtb. The cytotoxicity assessment indicated that the compounds were not cytotoxic against HEK 293 cells. The compounds could have a novel mechanism to anti-Mtb as they can inhibit drug sensitive and drug resistant Mtb. (C) 2015 Elsevier Ltd. All rights reserved.