2-(4-叔丁基苯基)-5-(氯甲基)-1,3,4-恶二唑 | 754214-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-叔丁基苯基)-5-(氯甲基)-1,3,4-恶二唑
• 英文名称: 2-(chloromethyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole
• 英文别名: 2-[4-(tert-Butyl)phenyl]-5-(chloromethyl)-1,3,4-oxadiazole；2-(4-tert-butylphenyl)-5-(chloromethyl)-1,3,4-oxadiazole
• CAS: 754214-36-3
• 化学式: C₁₃H₁₅ClN₂O
• mdl: MFCD06797381
• 分子量: 250.728
• InChiKey: LKDRJSXAQNUYMR-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70°
• 沸点：
  350.2±52.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (2R)-3-(2-methylbenzothiazol-5-yloxy)-1-piperazinylpropan-2-ol 、 2-(4-叔丁基苯基)-5-(氯甲基)-1,3,4-恶二唑 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-{4-[5-(4-tert-butyl-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-piperazin-1-yl}-3-(2-methyl-benzothiazol-5-yloxy)-propan-2-ol
  参考文献：
  名称：

  CVT-4325: a potent fatty acid oxidation inhibitor with favorable oral bioavailability

  摘要：

  New inhibitors of palmitoyl-CoA oxidation are based on the introduction of nitrogen heterocycles in the 'Western Portion' of the molecule. SAR studies led to the discovery of CVT-4325 (shown), a potent FOXi (IC50 = 380 nM rat mitochondria) with favorable PK properties (F= 93%, t(1/2) = 13.6 h, dog). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.077
• 作为产物：
  描述：

  对叔丁基苯甲酸 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 32.25h， 生成 2-(4-叔丁基苯基)-5-(氯甲基)-1,3,4-恶二唑
  参考文献：
  名称：

  Structural Variations in the Central Heterocyclic Scaffold of Tripartite 2,6-Difluorobenzamides: Influence on Their Antibacterial Activity against MDR Staphylococcus aureus

  摘要：

  本研究制备了五个系列的杂环三方 2,6-二氟苯甲酰胺，即 1,2,3-三唑、1,2,4- 和 1,3,4-恶二唑，它们是已报道的抗葡萄球菌模型化合物的类似物。目的是研究杂环中心支架的性质对三种金黄色葡萄球菌菌株（包括两种耐药菌株）生物活性的影响。在新收集的 15 种化合物中，一种 3-(4-叔丁基苯基)-1,2,4-恶二唑通过一个亚甲基与 2,6-二氟苯甲酰胺分子相连（II.c），根据菌株的不同，其最小抑制浓度介于 0.5 至 1 µg/mL 之间。随后对 II.c 进行的研究表明，它以细菌的分裂体为靶标，对人类没有细胞毒性。

  DOI：

  10.3390/molecules27196619

文献信息

• Anthracene-tethered aminomethyl oxadiazole chemosensor: a probe offering selective chromo- and fluorogenic signalings for targeting Cu(II)
  作者：Sabir H. Mashraqui、Tabrez Khan、Mukesh Chandiramani、Rupesh Betkar、Kiran Poonia

  DOI：10.1007/s10847-009-9717-4

  日期：2010.8

  A new optical chemosensor featuring anthracene as a fluorophore and an aminomethyl oxadiazole moiety as a bidentate chelate has been synthesized. From photophysical studies, we find the probe to offer remarkably selective chromo- and fluorogenic signaling responses towards biologically and environmentally significant Cu2+. In the presence of Cu2+, fluorescence is quenched to the extent of 95%, while the absorbance due to the anthracene chromophore is nearly completely bleached out. On the other hand, Li+, Na+, K+, Ba2+, Ca2+, Zn2+, Mg2+, Cd2+, Co2+, Ni2+, Ag+, Pb2+ and Hg2+ even at 10 times higher concentration than Cu2+ do not cause detectable photophysical perturbations. The stability constants, logK for Cu2+ were calculated to be 4.36 and 4.76 on the basis of spectrophotometric and fluorimetric titrations, respectively. However, logKs for other metal ions are too low (<0.1) to pose any interferences in the optical detection of Cu2+. Though, not fully defined, the uncommon phenomenon of the absorbance bleaching by Cu2+ is tentatively explained by invoking the involvement of non-covalent anthracene-Cu2+ complex.

  我们合成了一种新的光学化学传感器，它以蒽为荧光团，以氨基甲基噁二唑分子为双叉螯合物。通过光物理研究，我们发现该探针对具有生物和环境意义的 Cu2+ 具有显著的选择性发色和荧光信号反应。在 Cu2+ 存在的情况下，荧光被淬灭 95%，而蒽发色团的吸光度几乎完全被漂白。另一方面，Li+、Na+、K+、Ba2+、Ca2+、Zn2+、Mg2+、Cd2+、Co2+、Ni2+、Ag+、Pb2+ 和 Hg2+ 即使浓度比 Cu2+ 高 10 倍，也不会引起可检测到的光物理扰动。根据分光光度法和荧光滴定法计算，Cu2+ 的稳定常数 logK 分别为 4.36 和 4.76。然而，其他金属离子的 logK 太低（0.1），不会对 Cu2+ 的光学检测造成任何干扰。Cu2+ 对吸光的漂白这一不常见的现象虽然还没有完全确定，但可以初步解释为非共价蒽-Cu2+ 复合物的参与。
• Synthesis and Antimicrobial Properties of 1,3,4-Oxadiazole Analogs Containing Dibenzosuberane Moiety
  作者：Manjunath Moger、Vijay Satam、Darshan Raj C. Govindaraju、A. S. Paniraj、Vadiraj S. Gopinath、Rama Mohan Hindupura、Hari N. Pati

  DOI：10.5935/0103-5053.20130275

  日期：——

  A series of ten novel 1,3,4-oxadiazole analogs containing dibenzosuberane moiety were synthesized using linear as well as convergent synthesis approach. All the compounds were characterized by mass spectrometry, infrared (IR), H-1 and C-13 nuclear magnetic resonance (H-1 NMR and C-13 NMR) spectroscopies and elemental analysis. These compounds were evaluated for antibacterial and antifungal activities. Among ten analogs, four compounds, namely, 8a, 8d, 8e and 8j were found to be highly active antibacterial and antifungal agents.
• Microwave‐Assisted One‐Step Synthesis of Substituted 2‐Chloromethyl‐1,3,4‐oxadiazoles
  作者：Reina Natero、Dmitry O. Koltun、Jeffery A. Zablocki

  DOI：10.1081/scc-200025582

  日期：2004.1.1

  We have developed a simple one-step synthesis of 2-chloromethyl-1,3,4-oxadiazoles from commercially available acylhydrazides using 1-chloro-2,2,2-trimethoxyethane as a solvent under microwave irradiation.
• CVT-4325: a potent fatty acid oxidation inhibitor with favorable oral bioavailability
  作者：Elfatih Elzein、Prabha Ibrahim、Dmitry O. Koltun、Ken Rehder、Kevin D. Shenk、Timothy A. Marquart、Bob Jiang、Xiaofen Li、Reina Natero、Yuan Li、Marie Nguyen、Suresh Kerwar、Nancy Chu、Daniel Soohoo、Jia Hao、Victoria Y. Maydanik、David A. Lustig、Dewan Zeng、Kwan Leung、Jeff A. Zablocki

  DOI：10.1016/j.bmcl.2004.09.077

  日期：2004.12

  New inhibitors of palmitoyl-CoA oxidation are based on the introduction of nitrogen heterocycles in the 'Western Portion' of the molecule. SAR studies led to the discovery of CVT-4325 (shown), a potent FOXi (IC50 = 380 nM rat mitochondria) with favorable PK properties (F= 93%, t(1/2) = 13.6 h, dog). (C) 2004 Elsevier Ltd. All rights reserved.
• Structural Variations in the Central Heterocyclic Scaffold of Tripartite 2,6-Difluorobenzamides: Influence on Their Antibacterial Activity against MDR Staphylococcus aureus
  作者：Thibaut Barbier、Cédric Badiou、Floriane Davy、Yves Queneau、Oana Dumitrescu、Gérard Lina、Laurent Soulère

  DOI：10.3390/molecules27196619

  日期：——

  Five series of heterocyclic tripartite 2,6-difluorobenzamides, namely 1,2,3-triazoles, 1,2,4- and 1,3,4-oxadiazoles, analogs of reported model anti-staphylococcal compounds, were prepared. The purpose was to investigate the influence of the nature of the heterocyclic central scaffold on the biological activity against three strains of S. aureus, including two drug-resistant ones. Among the 15 compounds of the new collection, a 3-(4-tert-butylphenyl)-1,2,4-oxadiazole linked via a methylene group with a 2,6-difluorobenzamide moiety (II.c) exhibited a minimal inhibitory concentration between 0.5 and 1 µg/mL according to the strain. Subsequent studies on II.c demonstrated no human cytotoxicity, while targeting the bacterial divisome.

  本研究制备了五个系列的杂环三方 2,6-二氟苯甲酰胺，即 1,2,3-三唑、1,2,4- 和 1,3,4-恶二唑，它们是已报道的抗葡萄球菌模型化合物的类似物。目的是研究杂环中心支架的性质对三种金黄色葡萄球菌菌株（包括两种耐药菌株）生物活性的影响。在新收集的 15 种化合物中，一种 3-(4-叔丁基苯基)-1,2,4-恶二唑通过一个亚甲基与 2,6-二氟苯甲酰胺分子相连（II.c），根据菌株的不同，其最小抑制浓度介于 0.5 至 1 µg/mL 之间。随后对 II.c 进行的研究表明，它以细菌的分裂体为靶标，对人类没有细胞毒性。