N-phenyl-(5-benzyl-[1,3,4]oxadiazol-2-yl)-amine | 2027-70-5

• 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: N-phenyl-(5-benzyl-[1,3,4]oxadiazol-2-yl)-amine
• 英文别名: 5-benzyl-N-phenyl-1,3,4-oxadiazole-2-amine；5-benzyl-N-phenyl-1,3,4-oxadiazol-2-amine；(5-benzyl-[1,3,4]oxadiazol-2-yl)-phenyl-amine；JL0200；2-Benzyl-5-phenylamino-1,3,4-oxadiazol；5-Anilino-2-benzyl-1,3,4-oxadiazol
• CAS: 2027-70-5
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: XEYXALFBHVEWEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酸肼 在 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 N-phenyl-(5-benzyl-[1,3,4]oxadiazol-2-yl)-amine
  参考文献：
  名称：

  2 (5) - [苄基或氰甲基] -1,3,4-恶二唑的合成与反应

  摘要：

  一系列五元杂环，即5-（苄基或氰甲基）-3-乙酰基-2,2-二取代-1,3,4-恶二唑啉（3a-e），2,5-二取代-1,3,4 -恶二唑 (4a, b), 2-羟基-5- (苄基或氰甲基) -1,3,4-恶二唑 (5a, b), 1,2,5-三取代-1,3,4-三唑 (6a , b), 和 2- (苄基或氰基-甲基)-1,3,4-恶二唑-5-硫醇 (10a, b), 合成。因此制备了5-氯-2-苄基-1,3,4-恶二唑7。胺、肼和叠氮化钠与 7 反应分别得到相应的 2-芳基氨基 (8a, b)、5-肼或苯肼 (8c, d) 和 2-叠氮衍生物 9。曼尼希碱 (11a, b) 通过仲胺与 9a 的反应制备。5-羧甲硫基-1,3,4-恶二唑（12a，b）及其乙酯（13a，b）也被制备。

  DOI：

  10.1002/ardp.19903230908

文献信息

• [EN] NOVEL AZOLES AND RELATED DERIVATIVES AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS (NNRTIS) IN ANTIVIRAL THERAPY (HIV)<br/>[FR] NOUVEAUX AZOLES ET DÉRIVÉS APPARENTÉS À TITRE D'INHIBITEURS NON NUCLÉOSIDIQUES DE TRANSCRIPTASE INVERSE (NNRTIS) EN THÉRAPIE ANTIVIRALE (VIH)
  申请人：UNIV YALE

  公开号：WO2009005811A1

  公开（公告）日：2009-01-08

  The present invention relates to novel heterocyclic compounds, including oxadiazole compounds, pharmaceutical compositions and their use in the inhibition of reverse transcriptase and the treatment of HIV (1 and 2) infections, AIDS and ARC and other viral infections.

  本发明涉及新颖的杂环化合物，包括噁二唑化合物，药物组合物及其在抑制逆转录酶以及治疗HIV（1和2）感染、艾滋病和ARC以及其他病毒感染中的用途。
• Hypervalent iodine(V) mediated mild and convenient synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Girish Prabhu、V.V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.05.154

  日期：2012.8

  A simple protocol for the synthesis of 2-amino-1,3,4-oxadiazoles starting from the corresponding acylhydrazides by cyclodesulfurization of intermediate acylthiosemicarbazides mediated by o-iodoxybenzoic acid in good yields has been described. The protocol is mild with wide substrate scope, and thus a range of 2-amino-1,3,4-oxadiazoles have been prepared.

  已经描述了一种简单的方案，该方案通过由邻碘代碘苯甲酸介导的中间体酰基硫代氨基脲在高产率下进行环脱硫，从相应的酰肼开始合成2-氨基-1,3,4-恶二唑。该方案温和，底物范围广，因此已制备了一系列的2-氨基-1,3,4-恶二唑。
• Novel azoles and related derivatives as non-nucleoside reverse transcriptase inhibitors (nnrtis) in antiviral therapy (hiv)
  申请人：Jorgensen William L.

  公开号：US20100168190A1

  公开（公告）日：2010-07-01

  The present invention relates to novel heterocyclic compounds, including oxadiazole compounds, pharmaceutical compositions and their use in the inhibition of reverse transcriptase and the treatment of HIV (1 and 2) infections, AIDS and ARC and other viral infections.

  本发明涉及新型杂环化合物，包括噁唑化合物，制药组合物及其在抑制反转录酶和治疗HIV（1和2）感染，艾滋病和ARC以及其他病毒感染方面的用途。
• Efficient one-pot synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Eugene L. Piatnitski Chekler、Hassan M. Elokdah、John Butera

  DOI：10.1016/j.tetlet.2008.09.057

  日期：2008.11

  A convenient one-pot method for the preparation of substituted 2-amino-1,3,4-oxadiazoles has been developed. The method is a significant improvement over previously reported syntheses. Reaction of carboxylic acids with thiosemicarbazides afforded the corresponding oxadiazoles in moderate to good yields. In general, the products precipitated from the reaction mixture, and were collected by filtration. In most of the cases, no chromatographic separations were required. To explore the scope and limitations of this reaction, various aliphatic, aromatic, and heteroaromatic carboxylic acids were reacted with different substituted thiosemicarbazides. The influence of R-1 and R-2 substituents on the reaction yield and additional results demonstrating the versatility of this method are presented. (c) 2008 Elsevier Ltd. All rights reserved.
• <i>o</i>-Iodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles
  作者：Pramod S. Chaudhari、Sagar P. Pathare、Krishnacharaya G. Akamanchi

  DOI：10.1021/jo2025509

  日期：2012.4.20

  A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.