3-(4-chlorophenyl)-5-methyl-2-oxo-Δ⁴-1,3,4-oxadiazole | 269392-85-0

• 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: 3-(4-chlorophenyl)-5-methyl-2-oxo-Δ⁴-1,3,4-oxadiazole
• 英文别名: 3-(4-chlorophenyl)-5-methyl-1,3,4-oxadiazol-2(3H)-one；3-(4-Chlorophenyl)-5-methyl-3H-1,3,4-oxadiazole-2-one；3-(4-chlorophenyl)-5-methyl-1,3,4-oxadiazol-2-one
• CAS: 269392-85-0
• 化学式: C₉H₇ClN₂O₂
• 分子量: 210.62
• InChiKey: NRTSNFJCUKMYMA-UHFFFAOYSA-N

物化性质

• 沸点：
  290.4±42.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-5-methyl-2-oxo-Δ⁴-1,3,4-oxadiazole 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-(4-chlorophenoxy)ethyl)-2-(4-chlorophenyl)-5-methyl-2H-1,2,4-triazol-3(4H)-one
  参考文献：
  名称：

  Synthesis, characterization and in vitro anticancer evaluation of novel 1,2,4-triazolin-3-one derivatives

  摘要：

  A series of novel 2-(4-chlorophenyl)-5-methyl-4-(2-amine/oxy-ethyl)-2,4-dihydro-[1,2,4]triazol-3-one (5a-t) were synthesized and in vitro anticancerous action of the resulting compounds was studied against NCI-60 Human Tumor Cell Line at a single high dose (10(-5) M) concentration for primary cytotoxicity assay. Among the tested compounds (5a-e, 5g-h, 5k, 5p), the compound 5g (NSC: 761736/1) was further evaluated for five dose criteria at five different minimal concentrations against the full panel of 60 human tumor cell lines which exhibited activity against Leukemia (GI(50): 1.10 mu M), Non-Small Cell Lung Cancer (GI(50): 1.00 mu M), Renal Cancer (GI(50): 1.00 mu M), Colon Cancer (GI(50): 1.66 mu M), CNS Cancer (GI(50): 1.36 mu M), Melanoma (GI(50): 1.82 mu M), Ovarian Cancer (GI(50): 1.64 mu M) and Breast Cancer (GI(50): 1.69 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.004
• 作为产物：
  描述：

  3-(4-氯苯基)-1,2,3-氧杂二氮唑-3-鎓-5-酸内盐 在 溴 、 乙酸酐 作用下， 生成 3-(4-chlorophenyl)-5-methyl-2-oxo-Δ⁴-1,3,4-oxadiazole
  参考文献：
  名称：

  sydnone环转变为恶二唑啉酮。从3-芳基sydnones方便地一锅合成3-芳基-5-甲基-1,3,4-恶二唑啉-2-酮及其抗菌活性。

  摘要：

  通过与溴在乙酸酐中的一步反应，将3-芳基sydnones（Ia-u）转化为相应的3-芳基-5-甲基-1,3,4-恶二唑啉-2-酮（IIIa-u）。在所有这些化合物的初步筛选中，卤素取代的衍生物已显示出与所用标准药物相同的抗微生物活性。

  DOI：

  10.1016/s0014-827x(99)00103-2

文献信息

• The reaction of sydnones with bromine in acetic anhydride revisited: a new route to 5-substituted-3-aryl-1,3,4-oxadiazol-2(3H)-ones from N-aryl-N-bromocarbonylhydrazines
  作者：Jonathan Michael Tumey、Thijs Gerritsen、Jimmy Klaasen、Karunakar Reddy Madaram、Kenneth Turnbull

  DOI：10.24820/ark.5550190.p010.488

  日期：——

  The reaction of 3-phenylsydnone with bromine in acetic anhydride to form 5-methyl-3-phenyl-1,3,4-oxadiazol2(3H)-one has been reexamined and improved. A new mechanism involving a bromocarbonylhydrazine species is proposed and its intermediacy is supported by the observation that it reacts with acetic anhydride to yield the corresponding 1,3,4-oxadiazol-2(3H)-one. The process has been expanded to the

  3-苯基悉尼酮与溴在乙酸酐中反应生成5-甲基-3-苯基-1,3,4-恶二唑2(3H)-酮的反应得到了重新研究和改进。提出了一种涉及溴羰基肼物种的新机制，其中间体得到了观察结果的支持，即它与乙酸酐反应生成相应的 1,3,4-恶二唑-2(3H)-one。该过程已扩展到酰氯的使用，并开发了 5-取代-3-芳基-1,3,4-恶二唑-2(3H)-酮的新型合成方法。
• C₅-Alkyl-1,3,4-Oxadiazol-2-ones Undergo Dealkylation upon Nitrogen Insertion to Form 2<i>H</i>-1,2,4-Triazol-3-ones: Synthesis of 1,2,4-Triazol-3-one Hybrids with Triazolothiadiazoles and Triazolothiadiazines
  作者：Pramod P. Kattimani、Ravindra R. Kamble、Atukuri Dorababu、Raveendra K. Hunnur、Atulkumar A. Kamble、H.C. Devarajegowda

  DOI：10.1002/jhet.2813

  日期：2017.7

  study emphasizes on the dealklylation of 3‐aryl‐5‐alkyl‐2‐oxo‐Δ4‐1,3,4‐oxadiazoles when reacted with formamide resulting in the formation of 2‐aryl‐2H‐1,2,4‐triazol‐3(4H)‐ones as major product. Subsequent reactions of 2‐aryl‐2H‐1,2,4‐triazol‐3(4H)‐one gave triazolo[3,4‐b][1,3,4]thiadiazoles and triazolo[3,4‐b][1,3,4]thiadiazines derivatives incorporated with 1,2,4‐triazol‐3‐one.

  本研究中强调的3-芳基-5-烷基-2-氧代- Δ的dealklylation 4 -1,3,4-恶二唑时，导致在2-芳基2的形成甲酰胺反应ħ -1,2，主要产品4-三唑-3（4 H）-1 。随后的2-芳基-2 H -1,2,4-三唑-3（4 H）-1反应产生了三唑[3,4- b ] [1,3,4]噻二唑和三唑[3,4- b ] [1,3,4]噻二嗪衍生物与1,2,4-三唑-3-酮结合。
• Synthesis and Biological Activity of Some Novel 4-(5-Mercapto-1,3,4-thiadiazol-2-yl)-2-phenyl-5-[2-phenylvinyl]-2,4-dihydro-3H-1,2,4-triazol-3-one
  作者：Kumar Sanjeev S. Lamani、Oblennavar Kortesh

  DOI：10.1155/2010/190179

  日期：——

  A novel and efficient route have been designed for the synthesis of 4-(5-mercapto-1,3,4-thiadiazol-2-yl)-2-phenyl-5-[2-phenylvinyl]-2,4-dihydro-3H-1,2,4-triazol-3-one. All the synthesized compound were characterized by elemental analysis, IR,¹H NMR,¹³C NMR and mass spectra. All the synthesized products were evaluated for their antibacterial activity againstB. SubtilisandE.Coliand antifungal activity againstA. nigerandC.Albicanrespectively. The results indicate that the present compounds may serve as better fungicides when compared to bactericides. The synthesized compounds have turned to be wonder by possessing antimicrobial properties.

  已为合成4-(5-巯基-1,3,4-噻二唑-2-基)-2-苯基-5-[2-苯基乙烯基]-2,4-二氢-3H-1,2,4-三唑-3-酮设计了一种新颖高效的合成途径。所有合成的化合物均通过元素分析、红外光谱、1H核磁共振谱、13C核磁共振谱和质谱进行了表征。所有合成的产物均对枯草芽孢杆菌和大肠杆菌的抗菌活性以及对黑曲霉和白色念珠菌的抗真菌活性进行了评估。结果表明，与杀菌剂相比，这些化合物可能更适用于作为杀真菌剂。合成的化合物通过具有抗微生物特性而表现出奇妙的效果。
• Facile TICl4-catalyzed synthesis of novel 1,2,4-triazoles appended to thiazoles
  作者：T. Gireesh、R. R. Kamble、R. K. Hunnur、T. Taj、M. Y. Kariduraganavar

  DOI：10.1007/s10593-011-0849-2

  日期：2011.10

  The reaction of sydnone-derived 3-aryl-5-methyl-1,3,4-oxadiazol-2(3H)-ones with thiourea and α-bromoacetophenone derivatives in the presence of a catalytic amount of TiCl4 produces 2-aryl-4-(4-aryl-1,3-thiazol-2-yl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-ones. The title compounds were screened for their antibacterial and antifungal activity. The toxicity of the compounds was evaluated in terms of

  在催化量的TiCl 4的存在下，由亚砜基衍生的3-芳基-5-甲基-1,3,4-恶二唑-2（3 H）-酮与硫脲和α-溴苯乙酮衍生物的反应生成了2-芳基-4-（4-芳基-1,3-噻唑-2-基）-5-甲基-2,4-二氢-3 H -1,2,4-三唑-3-酮。筛选标题化合物的抗菌和抗真菌活性。根据致突变性，致瘤性和生殖作用评估了化合物的毒性。计算了与药物相关的特性（ClogP，药物相似性和药物评分），并讨论了结构与活性之间的关系。
• Zinc Triflate Catalyzed Facile Synthesis of Novel 1,2,4-triazolinone Derivatives Using 3-arylsydnone as Synthon
  作者：Atukuri Dorababu、Ravindra Kamble、Pramod Kattimani

  DOI：10.2174/1570178611310070009

  日期：2013.7.1

  A series of novel tetrazoles (4a-k) and thiazolidinones (6a-k) appended to 2-aryl-1,2,4-triazolin-3-ones were efficiently synthesized from 3-arylsydnones (1a-k) in excellent yields using Zinc triflate as catalyst.

  使用3-芳基sydnones（1a-k）高效合成了一系列新型的偶氮四唑（4a-k）和噻唑烷酮（6a-k），该化合物与2-芳基-1,2,4-三唑啉-3-酮高效合成，使用三氟甲磺酸锌为催化剂。