ethyl 2-[(4-chlorophenyl)(ethoxy)methylene]hydrazinecarboxylate | 70249-86-4

• 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: ethyl 2-[(4-chlorophenyl)(ethoxy)methylene]hydrazinecarboxylate
• 英文别名: N(1)-Carbethoxyhydrazon；Ethyl 2-((4-chlorophenyl)(ethoxy)methylene]hydrazinecarboxylate；ethyl 4-chloro-N-ethoxycarbonylbenzenecarbohydrazonate
• CAS: 70249-86-4
• 化学式: C₁₂H₁₅ClN₂O₃
• 分子量: 270.716
• InChiKey: YDXCZAZPHSWVQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(4-chlorophenyl)(ethoxy)methylene]hydrazinecarboxylate 在 羟胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以61%的产率得到N'-{(4-Chloro-phenyl)-[(Z)-hydroxyimino]-methyl}-hydrazinecarboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4-hydroxy-4,5-dihydro-1,2,4-triazol-5-ones

  摘要：

  A series of hydroxamic acid ethoxycarbonylhydrazides was obtained by reactions of ester ethoxycarbonylhydrazones with hydroxylamine. The corresponding 3-substituted 4-hydroxy-4,5-dihydro-1,2,4-triazol-5-ones were synthesized by cyclization of these hydroxamic acid derivatives in basic medium.

  DOI：

  10.1007/bf00810474

文献信息

• Synthesis of new derivatives of 4-amino-2,4-dihydro-1,2,4-triazol-3-one as potential antibacterial agents
  作者：Frédérique Malbec、René Milcent、Patrick Vicart、Anne Marie Bure

  DOI：10.1002/jhet.5570210641

  日期：1984.11

  characterised by their sharp melting points, elemental analysis, ir and 1H nmr spectra. These new derivatives of 5-nitro-2-furaldehyde were screened for their antibacterial activities. Most of the compounds showed good activity against one test organism, Staphylococcus aureus. For a few compounds, C.M.I. ranged from 4 to 8 μg/ml (higher results than nitrofurantoin).

  三十个新的2-取代的-4-氨基-5-烷基或芳基-2,4-二氢-1,2,4-三唑-3-酮和十个2-取代的-5-烷基或芳基-4-（5-合成了硝基-2-糠基亚氨基）氨基-2,4-二氢-1,2,4-三唑-3-酮，并通过其尖锐的熔点，元素分析，ir和1 H nmr光谱对其进行了表征。筛选了5-硝基-2-呋喃甲醛的这些新衍生物的抗菌活性。大多数化合物对一种测试生物金黄色葡萄球菌显示出良好的活性。对于一些化合物，CMI范围为4至8μg/ ml（比呋喃妥因更高的结果）。
• Synthesis and antimicrobial activities of some new 1,2,4-triazole derivatives
  作者：NESLİHAN DEMİRBAŞ、AHMET DEMİRBAŞ、HACER BAYRAK、HAKAN BEKTAŞ、ŞENGÜL ALPAY KARAOĞLU

  DOI：10.3906/kim-1004-570

  日期：——

  The synthesis of ethyl [3-(cyanomethyl)-5-alkyl-4H-1,2,4-triazol- 4-yl]carbamates (2a-d) was performed starting from ethyl 2-[ethoxy(4- (aryl)methylene]hydrazinecarboxylates (1a, 1b). The treatment of 2a with thiosemicarbazide afforded ethyl [3-[(5-amino-1,3,4-thiadiazol- 2-yl)methyl]-5-(4-nitrophenyl)-4H-1,2,4-triazol-4-yl]carbamates (3a), whereas compound 2b produced 5-[4-amino-5-(4-methylphenyl)- 4H-1,2,4-triazol-3-yl]methyl}-1,3,4-thiadiazol-2-amine (3b) in the same reaction conditions. The treatment of tert-butyl 2-[2-(4-chlorophenyl)-1-ethoxyethylidene]hydrazinecarboxylate (5) with malonohydrazide or cyanoacethydrazide gave the corresponding 1,2,4-triazol-ylcarbamate derivatives (6 or 9); then the hydrolysis of these compounds resulted in the formation of 3-[4-amino-5-(4- chlorobenzyl)-4H-1,2,4-triazol-3-yl]methyl}-5-(4-chlorobenzyl)-4H- 1,2,4-triazol-4-amine (7) and [4-amino-5-(4-chlorobenzyl)-4H- 1,2,4-triazole-3-yl]acetonitrile (10), respectively. The synthesis of the Schiff base derivatives 3-(4-chlorobenzyl)-5-[5-(4-chloroben- zyl)-4-[(2-hydroxyphenyl-methylene)amino]-4H-1,2,4-triazol-3-yl]methyl} -N-(2-hydroxyphenylmethylene)-4H-1,2,4-triazol-4-amine (8), and (5-(4-chlorobenzyl)-4-[(2,6-dichlorophenyl)methylene]amino}-4H-1,2,4- triazol-3-yl)acetonitrile (12) was performed from the reaction of compounds 7 and 10 with salicyl aldehyde (for 8) or 2,6-dichlorobenzaldehyde (for 12), respectively. The treatment of compounds 5 or 10 with thiosemicarbazide gave 5-[4-amino-5-(4-chlorobenzyl)-4H-1,2,4-triazol- 3-yl]methyl}-1,3,4-thiadiazol-2-amine (11). All the newly synthesized compounds were screened for their antimicrobial activities and were found to possess good or moderate antimicrobial activity.

  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。
• 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。
• The synthesis of some new imidazole and triazole derivatives: crystal Structure and DFT-TDDFT investigation on electronic structure
  作者：Kemal Sancak、Yasemin Ünver、Hasan Tanak、Ismail Değirmencioğlu、Esra Dügdü、Mustafa Er、Şamil Işik

  DOI：10.1007/s10847-009-9714-7

  日期：2010.8

  A series of new N′-3-(1H-imidazol-1-yl)propylcarbamoyl-4-halogenebenzo hydrazonate (3a–b) were obtained by reaction Ethyl 2-((4-halogene phenyl) (ethoxy) methylene) hydrazinecarboxylate (1) and N-(3-aminopropyl)imidazole (2) at 120–140 °C. Compounds (4a–b) were obtained by the reaction compound 1 and N-(3-aminopropyl)imidazole (2) at 160–180 °C. The structures of compounds 3,4 have been inferred through UV–Vis, IR, 1H/13C NMR, mass spectrometry, elemental analyses, and X-ray crystallography. DFT level 6-31G (d) calculations provided structural information. The electronic structure of compound 3a has been studied by DFT level 6-31G (d) calculations using the X-ray data. The results are accordance with X-ray data.

  由 2-((4-卤代苯基)(乙氧基)亚甲基)肼羧酸乙酯 (1) 和 N-(3-氨基丙基)咪唑 (2) 在 120-140 ℃ 反应得到一系列新的 N′-3-(1H-咪唑-1-基)丙基氨基甲酰基-4-卤代苯肼(3a-b)。化合物 1 和 N-(3-氨基丙基)咪唑 (2) 在 160-180 ℃ 反应得到化合物 (4a-b)。化合物 3 和 4 的结构是通过紫外可见光、红外光谱、1H/13C NMR、质谱分析、元素分析和 X 射线晶体学推断出来的。DFT 6-31G (d) 级计算提供了结构信息。利用 X 射线数据，通过 DFT 6-31G (d) 级计算研究了化合物 3a 的电子结构。结果与 X 射线数据相符。