N-苄基-5-(2-甲基苯基)-1,3,4-恶二唑-2-胺 | 918964-44-0

• 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: N-苄基-5-(2-甲基苯基)-1,3,4-恶二唑-2-胺
• 英文名称: N-benzyl-(5-(2-methylphenyl)-[1,3,4]oxadiazol-2-yl)-amine
• 英文别名: N-Benzyl-5-(2-methylphenyl)-1,3,4-oxadiazol-2-amine
• CAS: 918964-44-0
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: LUXLVMKLMJVPBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-甲苯甲酰肼 在 吡啶 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 N-苄基-5-(2-甲基苯基)-1,3,4-恶二唑-2-胺
  参考文献：
  名称：

  Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles

  摘要：

  A facile and general protocol for the preparation of 2-amino-1,3,4- oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.

  DOI：

  10.1021/jo0618730

文献信息

• <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.
• Prabhu, Girish; Madhu, Chilakapathi; Sureshbabu, Vommina V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 865 - 870
  作者：Prabhu, Girish、Madhu, Chilakapathi、Sureshbabu, Vommina V.

  DOI：——

  日期：——
• Superior Reactivity of Thiosemicarbazides in the Synthesis of 2-Amino-1,3,4-oxadiazoles
  作者：Sarah J. Dolman、Francis Gosselin、Paul D. O'Shea、Ian W. Davies

  DOI：10.1021/jo0618730

  日期：2006.12.1

  A facile and general protocol for the preparation of 2-amino-1,3,4- oxadiazoles is reported. This method relies on a tosyl chloride/pyridine-mediated cyclization of a thiosemicarbazide, which is readily prepared by acylation of a given hydrazide with the appropriate isothiocyanate. Cyclization of the thiosemicarbazide consistently outperforms the analogous semicarbazide cyclization under these conditions, for 18 distinct examples. Utilizing this protocol, we have prepared 5-alkyl- and 5-aryl-2-amino-1,3,4-oxadiazoles in 78-99% yield.