N(1)-Carbethoxyhydrazon | 70249-88-6

• 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(1)-Carbethoxyhydrazon
• 英文别名: ethyl 2-[-ethoxy(p-tolyl)methylene]hydrazine carboxylate；ethyl N-ethoxycarbonyl-4-methylbenzenecarbohydrazonate
• CAS: 70249-88-6
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: IXYQTCXYGPHEBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N(1)-Carbethoxyhydrazon 在 三氟乙酸 作用下， 反应 11.0h， 生成 5-{[4-amino-5-(4-methylphenyl)-4H-1,2,4-triazol-3-yl]methyl}-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives

  摘要：

  合成乙基[3-(氰甲基)-5-烷基-4H-1,2,4-三氮唑-4-基]氨基甲酸酯（2a-d）是从乙基2-[乙氧基(4-芳基)亚甲基]肼甲酸酯（1a, 1b）开始进行的。将化合物2a与硫半脲反应后得到了乙基[3-[(5-氨基-1,3,4-噻二唑-2-基)甲基]-5-(4-硝基苯基)-4H-1,2,4-三氮唑-4-基]氨基甲酸酯（3a），而化合物2b则在相同反应条件下产生了5-{[4-氨基-5-(4-甲基苯基)-4H-1,2,4-三氮唑-3-基]甲基}-1,3,4-噻二唑-2-胺（3b）。将叔丁基2-[2-(4-氯苯基)-1-乙氧基乙烯基]肼甲酸酯（5）与丙二酸肼或氰乙肼反应得到了相应的1,2,4-三氮唑基氨基甲酸酯衍生物（6或9）；然后这些化合物的水解反应形成了3-{[4-氨基-5-(4-氯苯甲基)-4H-1,2,4-三氮唑-3-基]甲基}-5-(4-氯苯甲基)-4H-1,2,4-三氮唑-4-胺（7）和[4-氨基-5-(4-氯苯甲基)-4H-1,2,4-三氮唑-3-基]乙腈（10）。从化合物7和10与水杨醛（8）或2,6-二氯苯甲醛（12）反应中合成了Schiff碱衍生物3-(4-氯苯甲基)-5-{[5-(4-氯苯甲基)-4-[(2-羟基苯基-亚甲基)氨基]-4H-1,2,4-三氮唑-3-基]甲基}-N-(2-羟基苯基亚甲基)-4H-1,2,4-三氮唑-4-胺（8）和(5-(4-氯苯甲基)-4-{[(2,6-二氯苯基)亚甲基]氨基}-4H-1,2,4-三氮唑-3-基)乙腈（12）。将化合物5或10与硫半脲反应生成了5-{[4-氨基-5-(4-氯苯甲基)-4H-1,2,4-三氮唑-3-基]甲基}-1,3,4-噻二唑-2-胺（11）。所有新合成的化合物都进行了抗微生物活性筛选，结果发现具有良好或中等的抗微生物活性。

  DOI：

  10.3906/kim-1004-570

文献信息

• Synthesis and Antimicrobial Activities of Some New 1,2,4-Triazole Derivatives
  作者：Hakan Bektaş、Nesrin Karaali、Deniz Şahin、Ahmet Demirbaş、Şengül Alpay Karaoglu、Neslihan Demirbaş

  DOI：10.3390/molecules15042427

  日期：——

  Some novel 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazol-3-one (3, 6, 8, 9) derivatives and or 3-(4-methylphenyl)[1,2,4]triazolo[3,4-b][1,3]benzoxazole (5) were synthesized from the reaction of various ester ethoxycarbonylhydrazones (1a-e) with several primary amines. The synthesis of 4-amino-5-(4-chlorophenyl)-2-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (13) was

  一些新的 4,5-二取代-2,4-二氢-3H-1,2,4-三唑-3-酮 (3, 6, 8, 9) 衍生物和/或 3-(4-甲基苯基)[1,2 ,4] 三唑并 [3,4-b][1,3] 苯并恶唑 (5) 由各种酯乙氧基羰基腙 (1a-e) 与几种伯胺反应合成。4-氨基-5-(4-氯苯基)-2-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2的合成， 4-三唑-3-一(13)由4-氨基-5-(4-氯苯基)-2,4-二氢-3H-1,2,4-三唑-3-一(2)为原料，由四脚步; 然后使用 4-甲氧基苯甲醛将 13 转化为相应的席夫碱 (14)。最后，以吗啉或甲基哌嗪为胺组分，得到14的两种曼尼希碱衍生物。
• Synthesis, crystal structure, and antioxidant properties of novel 1,2,4-triazol-5-ones containing 3,4-dimethoxyphenyl and 3,4-dihydroxyphenyl moiety
  作者：YASEMİN ÜNVER、SEVGİ MEYDANAL、KEMAL SANCAK、DİLEK ÜNLÜER、REŞAT USTABAŞ、ESRA DÜĞDÜ

  DOI：10.3906/kim-1006-707

  日期：——

  A series of new 4-(3,4-dimethoxyphenethyl)-5-akyl/aryl-2H- 1,2,4-triazol-3(4H)-ones (3a-g) was obtained by the reaction of ethyl 2-(ethoxy)(alkylidene/arylidene)hydrazinecarboxylate (1) and 2-(3,4-dimethoxyphen- yl)ethanamine (2). Compounds 4a-f and 5 were synthesized from the reaction of corresponding compounds 3a-f and 3g with BBr_3, respectively. With elemental analysis, IR, ^1H-NMR, and ^13C-NMR spectral data, 14 newly synthesized compounds were characterized. The structure of compound 3a was inferred through IR, ^1H- and ^13}C-NMR, elemental analysis, and X-ray spectral techniques. In addition, the newly synthesized chemicals were screened for their antioxidant properties. Among the chemicals tested, 4a, 4c, 4d, 4f, and 5 exhibited the highest degree of antioxidant activity.

  由 2-(乙氧基)(亚烷基/亚芳基)肼羧酸乙酯 (1) 和 2-(3,4-二甲氧基苯-基)乙胺 (2) 反应得到一系列新的 4-(3,4-二甲氧基苯乙基)-5-酰基/芳基-2H- 1,2,4-三唑-3(4H)-酮 (3a-g)。 化合物 4a-f 和 5 分别由相应的化合物 3a-f 和 3g 与 BBr_3 反应合成。 通过元素分析、红外光谱、^1H-NMR 和 ^13C-NMR光谱数据，对 14 个新合成的化合物进行了表征。 通过红外光谱、^1H-、^13}C-NMR、元素分析和 X 射线光谱技术，推断出了化合物 3a 的结构。 此外，还对新合成的化学物质进行了抗氧化性筛选。 在测试的化学品中，4a、4c、4d、4f 和 5 的抗氧化活性最高。
• Reaction of Ester Ethoxycarbonylhydrazones with Aliphatic Diamines
  作者：Aykut A. Ikizler、Kemal Sancak

  DOI：10.1135/cccc19950903

  日期：——

  Reaction of esters of (N-ethoxycarbonyl)alkanehydrazonic acids with aliphatic diamines were prepared α,ω-bis(3-alkyl-4,5-dihydro-1H -1,2,4-triazol-5- one-4-yl)alkanes. All compounds were characterized by elemental analyses, IR and ¹H NMR spectra.

  酯类（N-乙氧羰基）烷基肼酸与脂肪族二胺反应制备了α,ω-双(3-烷基-4,5-二氢-1H-1,2,4-三唑-5-酮-4-基)烷烃。所有化合物均通过元素分析、红外光谱和1H核磁共振光谱进行了表征。
• Experimental and theoretical studies of the molecular structure of 4-(3-(1H-imidazol-1-yl)propyl)-5-p-tolyl-2H-1,2,4-triazol-3(4H)-one
  作者：Reşat Ustabaş、Nevin Süleymanoğlu、Hasan Tanak、Yelda Bingöl Alpaslan、Yasemin Ünver、Kemal Sancak

  DOI：10.1016/j.molstruc.2010.09.018

  日期：2010.12

  The triazol-imidazol compound, 4-(3-(1H-imidazol-1-yl)propyl)-5-p-tolyl-2H-1,2,4-triazol-3(4H)-one (3), (C15H17N5O), was prepared and characterized by H-1 NMR, C-13 NMR, IR and single-crystal X-ray diffraction. By using the density functional theory (DFT) method with 6-31G(d) basis set, the molecular geometry, vibrational frequencies and gauge including atomic orbital (CIAO) H-1 and C-13 NMR chemical shift values of the title compound (3) in the ground state were calculated and compared with the experimental data. The calculated results are show that the optimized geometry can well reproduce the crystal structure. X-ray, FT-IR and NMR spectral results of the title compound (3) indicate that the compound exists as keto form. To determine most favorable conformation as theoretically, molecular energy profile of the title compound (3) were obtained as a function of the selected torsion angles T(N1-C8-C7-C6), T1 and T(C8-N1-C10-C11), T2, which is varied from -180 degrees to +180 degrees in every 10 by semi-empirical (PM3) calculations. In addition, DFT calculations of the title compound (3), molecular electrostatic potential and frontier molecular orbitals were performed at B3LYP/6-31G(d) level of theory. (C) 2010 Elsevier B.V. All rights reserved.
• Ikizler; Demirbas; Demirbas, Polish Journal of Chemistry, 1996, vol. 70, # 9, p. 1114 - 1120
  作者：Ikizler、Demirbas、Demirbas、Ikizler

  DOI：——

  日期：——