4-benzylidenamino-[1,2,4]triazolidine-3,5-dione | 4114-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-benzylidenamino-[1,2,4]triazolidine-3,5-dione
• 英文别名: 4-Benzylidenamino-[1,2,4]triazolidin-3,5-dion；4-Benzylidenamino-urazol；N-Benzylidenamino-urazol；4-Benzalaminourazol；4-(benzylideneamino)-1,2,4-triazolidine-3,5-dione
• CAS: 4114-10-7
• 化学式: C₉H₈N₄O₂
• 分子量: 204.188
• InChiKey: QAAGQSWYWAIPRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  蒽 、 4-benzylidenamino-[1,2,4]triazolidine-3,5-dione 在 溶剂黄146 、 sodium nitrite 作用下， 以 乙酸乙酯 为溶剂， 反应 0.2h， 以82%的产率得到9,10-(4’-benzalamino)urazolo-9,10-dihydroanthracene
  参考文献：
  名称：

  A Convenient Methodology for the in situ Oxidation of 4-Substituted Urazoles. Setting Up a One-Pot Procedure for the Efficient Protection of Dienes

  摘要：

  The oxidation of 4-substituted urazoles to the corresponding 1,2,4-triazoline-3,5-diones can be performed selectively in the presence of dienic systems by the action of the nitrosonium ion, formed in situ by stoichiometric amounts of sodium nitrite and acetic acid. This convenient methodology is mild, fast, and allows the efficient protection of dienic systems in a one-pot procedure. The dienes were not affected whatsoever by the nitrosonium ion, and react extremely fast with triazolinediones; promptly forming the corresponding Diels-Alder cycloadducts in good to excellent yields. The reaction medium did not affect steroids having an extra double bond at the side chain or an acid-labile spiroketal moiety.

  DOI：

  10.3987/com-12-12637
• 作为产物：
  描述：

  4-氨基-(4H)-1,2,4-噻唑-3,5-二醇 、 苯甲醛 以 水 为溶剂， 反应 0.5h， 以100%的产率得到4-benzylidenamino-[1,2,4]triazolidine-3,5-dione
  参考文献：
  名称：

  A Convenient Methodology for the in situ Oxidation of 4-Substituted Urazoles. Setting Up a One-Pot Procedure for the Efficient Protection of Dienes

  摘要：

  The oxidation of 4-substituted urazoles to the corresponding 1,2,4-triazoline-3,5-diones can be performed selectively in the presence of dienic systems by the action of the nitrosonium ion, formed in situ by stoichiometric amounts of sodium nitrite and acetic acid. This convenient methodology is mild, fast, and allows the efficient protection of dienic systems in a one-pot procedure. The dienes were not affected whatsoever by the nitrosonium ion, and react extremely fast with triazolinediones; promptly forming the corresponding Diels-Alder cycloadducts in good to excellent yields. The reaction medium did not affect steroids having an extra double bond at the side chain or an acid-labile spiroketal moiety.

  DOI：

  10.3987/com-12-12637

文献信息

• Improved synthesis of 1,2,4-triazoline-3,5-dione derivatives of ergosterol and a new method for their reconversion to ergosterol
  作者：Derek H.R. Barton、Xavier Lusinchi、Jesús Sandoval Ramírez

  DOI：10.1016/s0040-4039(00)88078-8

  日期：1983.1

  The ergosterol diene system reacts in excellent yield with a series of 4-substituted 1,2,4-triazoline-3,5-diones generated by in situ oxidation of the appropriate hydrazides with phenylseleninic anhydride or phenylseleninic acid. Diaryltelluroxide and diphenylselenoxide are also efficient oxdants. The diene system can be smoothly regenerated by alkaline hydrolysis.

  麦角固醇二烯系统以优异的产率与一系列的4-取代的1,2,4-三唑啉-3,5-二酮反应，所述一系列的4-取代的1,2,4-三唑啉-3,5-二酮是通过适当的酰肼与苯硒酸二酐或苯基硒酸的原位氧化而生成的。二芳基四氢呋喃和二苯硒酸也是有效的氧化剂。二烯体系可以通过碱水解而平滑地再生。
• Curtius; Heidenreich, Journal fur praktische Chemie (Leipzig 1954), 1895, vol. <2> 52, p. 485
  作者：Curtius、Heidenreich

  DOI：——

  日期：——
• Barton; Lusinchi; Sandoval Ramirez, Bulletin de la Societe Chimique de France, 1985, vol. NO. 5, # 5, p. 849 - 858
  作者：Barton、Lusinchi、Sandoval Ramirez

  DOI：——

  日期：——