N'-hydroxybenzimidamide

• 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'-hydroxybenzimidamide
• 英文别名: 2-amino-2-phenylethenol
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: JNFPMBQDNRNAQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.25
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N'-hydroxybenzimidamide 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 65.0~100.0 ℃ 、689.28 Pa 条件下， 反应 4.0h， 生成 3-苯基-5-(4-甲氧基苯基)-1,2,4-恶二唑
  参考文献：
  名称：

  1,2,4-恶二唑和异恶唑的新型合成

  摘要：

  通过利用a肟和α，β-炔醛和/或酮之间的反应，描述了1,2,4-恶二唑和异恶唑的新型合成方法。从a胺肟和α，β-炔醛和/或酮获得的共轭加成产物在分别用碱和酸处理时分别得到1,2,4-恶二唑和异恶唑。1,2,4-氧杂二唑也可以在碱性条件下一锅法直接由a胺肟和α，β-炔醛合成。该反应对于各种起始化合物是通用的，并且可以耐受芳基，杂芳基和烷基的存在。

  DOI：

  10.1016/j.tet.2013.12.043
• 作为产物：
  描述：

  苯甲腈 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 为溶剂， 以87%的产率得到N'-hydroxybenzimidamide
  参考文献：
  名称：

  1,2,4-恶二唑和异恶唑的新型合成

  摘要：

  通过利用a肟和α，β-炔醛和/或酮之间的反应，描述了1,2,4-恶二唑和异恶唑的新型合成方法。从a胺肟和α，β-炔醛和/或酮获得的共轭加成产物在分别用碱和酸处理时分别得到1,2,4-恶二唑和异恶唑。1,2,4-氧杂二唑也可以在碱性条件下一锅法直接由a胺肟和α，β-炔醛合成。该反应对于各种起始化合物是通用的，并且可以耐受芳基，杂芳基和烷基的存在。

  DOI：

  10.1016/j.tet.2013.12.043

文献信息

• Brønsted acid-catalyzed simple and efficient synthesis of 1,2,4-triazoles and 1,2,4-oxadiazoles using 2,2,2-trichloroethyl imidates in PEG
  作者：Nakka Mangarao、Gajula Mahaboob Basha、Tadikonda Ramu、Rayavarapu Srinuvasarao、Sarakula Prasanthi、Vidavalur Siddaiah

  DOI：10.1016/j.tetlet.2013.10.147

  日期：2014.1

  A facile and highly efficient synthesis of 3,4,5-trisubstituted 1,2,4-triazoles and 3,5-disubstituted 1,2,4-oxadiazoles from 2,2,2-trichloroethyl imidates using PEG as a solvent and employing PTSA as the catalyst under mild conditions is described.

  使用PEG作为溶剂并使用PEG从2,2,2-三氯乙基酰亚胺酯轻松高效地合成3,4,5-三取代的1,2,4-三唑和3,5-二取代的1,2,4-恶二唑描述了在温和条件下作为催化剂的PTSA。
• Platinum(IV)-Mediated Nitrile-Amidoxime Coupling Reactions: Insights into the Mechanism for the Generation of 1,2,4-Oxadiazoles
  作者：Dmitrii S. Bolotin、Nadezhda A. Bokach、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1002/cplu.201100047

  日期：2012.1

  platinum(IV) complexes trans‐[PtCl4(RCN)2] (1: R=Et, 2: Ph, 3: NMe2) proceeds in a 1:1 molar ratio and leads to the monoaddition products [PtCl4(RCN)HNC(R)ONC(R′)NH2}] (7: R/R′: Et/CH2Ph, 8: Et/Ph, 9: NMe2/CH2Ph, 10: NMe2/Ph). Meanwhile, if the nucleophilic addition proceeds in a 2:1 molar ratio the reaction gives the bisaddition species [PtCl4HNC(R)ONC(R′)NH2}2] (11: R/R′=Et/Me, 12: Et/CH2Ph, 13:

  mid胺肟R'C（NH 2）NOH（4：R'= Me，5：CH 2 Ph，6：Ph）亲核加成到铂（IV）络合物反式-[PtCl 4（RCN）中2 ]（1：R =的Et，2：pH值，3：NME 2）前进以1：1的摩尔比，并导致单加成产物[氯铂酸4（RCN）H ñ C（R）ONC（R' ）NH 2 }]（7：R / R'：Et / CH 2 Ph，8：Et / Ph，9：NMe 2 / CH2 Ph，10：NMe 2 / Ph）。同时，如果在一个2的亲核加成来进行：1的摩尔比反应给出bisaddition物种[氯铂酸4 H Ñ C（R）ONC（R'）NH 2 } 2 ]（11：R / R'=的Et / Me，12：Et / CH 2 Ph，13：Et / Ph，14：Ph / Ph，15：NMe 2 / Me，16：NMe 2 / CH 2 Ph，17：NMe 2 / Ph。所有建筑群7
• Sodium Carbonate-Promoted Formation of 5-Amino-1,2,4-thiadiazoles and 5-Amino-1,2,4-selenadiazoles with Elemental Sulfur and Selenium
  作者：Jun-Xu Lin、Guo-Hui Liu、Li-Qiu Liu、Ying-Chun Wang、Yan He

  DOI：10.1021/acs.joc.3c01716

  日期：2024.1.5

  Sodium carbonate-promoted facile synthesis of 5-amino-1,2,4-thiadiazoles and 5-amino-1,2,4-selenadiazoles with elemental sulfur and selenium, respectively, was developed. This method was carried out with O2 in the air as the green oxidant, and it has several advantages, including low cost, low toxicity, and stable sulfur and selenium sources, good to excellent yields with water as the sole byproduct

  开发了碳酸钠促进的 5-氨基-1,2,4-噻二唑和 5-氨基-1,2,4-硒二唑分别与元素硫和硒的简便合成方法。该方法以空气中的O 2为绿色氧化剂，具有成本低、毒性低、硫源和硒源稳定、收率优良、副产物为水、操作简单等优点。和广泛的底物范围。初步机理研究表明1,2,4-噻二唑环和1,2,4-硒二唑环的形成经历了不同的过程。
• Amidrazone Complexes from a Cascade Platinum(II)-Mediated Reaction between Amidoximes and Dialkylcyanamides
  作者：Dmitrii S. Bolotin、Nadezhda A. Bokach、Andreii S. Kritchenkov、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1021/ic4000878

  日期：2013.6.3

  The aryl amidoximes R'C6H4C(NH2)=NOH (R' = Me, 2a; H, 2b; CN, 2c; NO2, 2d) react with the dialkylcyanamide platinum(II) complexes trans-[PtCl2(NCNAlk(2))(2)] (Alk(2) = Me-2, 1a; C5H10, 1b) in a 1:1 molar ratio in CHCl3 to form chelated mono addition products [3a-h]Cl, viz. [PtCl-(NCNAlk(2))(N) under barH=C(NR2)O (N) under bar =C(C6H4R')NH2}]Cl (Alk(2) = Me-2; R' = Me, a; H, b; CN, c; NO2, d; Alk(2) = C5H10; R' = Me, e; H, f; CN, g; NO2, h). In the solution, these species spontaneously transform to the amidrazone complexes [PtCl2(N) under barH=C(NR2)NC(C6H4R')(N) under barH(2)}] (7a h; 36-47%); this conversion proceeds more selectively (49-60% after column chromatography) in the presence of the base (PhCH2)(3)N. The observed reactivity pattern is specific for NCNAlk(2) ligands, and it is not realized for conventional alkyl- and arylnitrile ligands. The mechanism of the cascade reaction was studied by trapping the isocyanate intermediates [PtCl(NCO)(N) under barH=C(NR2)NC(C6H4R')(N) under bar NH2}] (5a-h) and also by ESI-MS identification of the ammonia complexes [PtCl(NH3)(N) under barH=C(NR2)NC(C6H4R')(N) under bar NH2)](+) ([6a-h]) in solution. The complexes [3a]Cl, [3c-h]Cl, 5a-h and 7ah- were characterized by elemental analyses, high resolution ESI-MS, IR, and H-1 NMR, techniques, while 5b, 5d, 5g, 7b, and 7e were also studied using single crystal X-ray diffraction.
• Recyclization of 5-Aryl-1H-pyrrole-2,3-diones with Amidoximes. Synthesis of Enamines Containing a 1,2,4-Oxadiazole Fragment
  作者：D. I. Antonov、M. V. Dmitriev、I. A. Kuchumov、A. N. Maslivets

  DOI：10.1134/s1070428024030023

  日期：2024.3