(1-[2-hydroxyphenyl]-ethylidene)hydrazinecarboxylic acid methyl ester | 246229-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (1-[2-hydroxyphenyl]-ethylidene)hydrazinecarboxylic acid methyl ester
• 英文别名: 2'-hydroxyacetophenone carbomethoxyhydrazone；2-hydroxyacetophenonemethylcarbazate；N'-[1-(2-hydroxyphenyl)ethylidene]methoxycarbohydrazide；methyl N-[1-(2-hydroxyphenyl)ethylideneamino]carbamate
• CAS: 246229-63-0
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: YDDKNJIGRRUFCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻甲酸甲酯苯磺酰胺 、 (1-[2-hydroxyphenyl]-ethylidene)hydrazinecarboxylic acid methyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  2的制备ħ -螺[苯并[ d ]异噻唑-3,3'-吡唑] -1,1-二氧代-2'（4' ħ）从二锂-carboxylates Ç（α），Ñ -carboalkoxyhydrazones和2- （氨基磺酰基）苯甲酸酯

  摘要：

  通过将二锂化的C（α），N-羰基烷氧基azo与锂化的2-（氨基磺酰基）苯甲酸甲酯缩合，然后用乙酸酐环化中间体，制得了各种取代的螺（苯并异噻唑-吡唑）。当使用碳甲氧基hydr或碳乙氧基hydr时，N-乙酰化产物；当使用碳-叔丁氧基hydr时，螺为NH产物。杂环化学杂志，46，231（2009）。

  DOI：

  10.1002/jhet.50
• 作为产物：
  描述：

  肼基甲酸甲酯 、 2'-羟基苯乙酮 以 乙醇 为溶剂， 以81.16 %的产率得到(1-[2-hydroxyphenyl]-ethylidene)hydrazinecarboxylic acid methyl ester
  参考文献：
  名称：

  Crystal design, spectroscopic analyses and antibacterial study of new carbazate ligands and their Cu(II) complexes

  摘要：

  DOI：

  10.1016/j.ica.2023.121421

文献信息

• A New Series of Proton/Charge Transfer Molecules: Synthesis and Spectral Studies of 2-(5-Aryl-1-carbomethoxy-1H-pyrazol-3-yl)phenols
  作者：Mary E. Rampey、Carrie E. Halkyard、Angela R. Williams、April J. Angel、Douglas R. Hurst、Jessica D. Townsend、Anne E. Finefrock、Charles F. Beam、Shannon L. Studer-Martinez

  DOI：10.1111/j.1751-1097.1999.tb07987.x

  日期：1999.8

  Abstract. The carbomethoxyhydrazone of 2′‐hydroxyacetophenone was trilithiated with excess lithium diisopropylamide and C‐acylated with a variety of benzoate esters followed by acid cyclization of the intermediates to 2‐(5‐aryl‐l‐car‐bomethoxy‐lHpyrazol‐3‐yl)phenols [3‐(2‐hydroxyphen‐yl)‐lH‐pyrazoles]. The products were characterized by Fourier transform‐IR, lH NMR, 13C NMR, UV‐visible absorption and fluorescence. All the derivatives in n ‐heptane have an absorption maximum at ˜304 nm and an extremely weak (φr= 10 4) fluorescence with maxima in the range of 335–460 nm. The broad range of fluorescence maxima and fluorescence quantum yields is attributed to varying contributions of charge transfer that are dependent on both the identity of the substituent and solvent polarity. A phenomenally large Stokes‐shifted fluorescence maximum at 620 nm was observed for 2‐(l‐car‐bomethoxy‐5‐[4‐dimethylaminophenyl]‐lff‐pyrazol‐3‐y1)phenol in n‐heptane and attributed to excited‐state intramolecular proton transfer. As a result, competitive excited‐state proton/charge transfer properties have been observed in the pyrazoles studied, of which the spectral properties can be fine tuned by substituent as well as solvent effects.
• Preparation of 2<i>H</i>-spiro[benzo[<i>d</i>]isothiazole-3,3′-pyrazole]-1, 1-dioxide-2′(4′<i>H</i>)-carboxylates from dilithiated<i>C</i>(α),<i>N</i>-carboalkoxyhydrazones and methyl 2-(aminosulfonyl)benzoate
  作者：Anna C. Dawsey、Chandra Potter、John D. Knight、Zachary C. Kennedy、Ellyn A. Smith、Amanda M. Acevedo-Jake、Andrew J. Puciaty、Clyde R. Metz、Charles F. Beam、William T. Pennington、Donald G. VanDerveer

  DOI：10.1002/jhet.50

  日期：2009.3

  A variety of substituted spiro(benzoisothiazole-pyrazoles) have been prepared by the condensation of dilithiated C(α),N-carboalkoxyhydrazones with lithiated methyl 2-(aminosulfonyl)benzoate followed by the cyclization of intermediates with acetic anhydride, which also resulted in spiro N-acetylated products when carbomethoxyhydrazones or carboethoxyhydrazones were used, and spiro NH products when

  通过将二锂化的C（α），N-羰基烷氧基azo与锂化的2-（氨基磺酰基）苯甲酸甲酯缩合，然后用乙酸酐环化中间体，制得了各种取代的螺（苯并异噻唑-吡唑）。当使用碳甲氧基hydr或碳乙氧基hydr时，N-乙酰化产物；当使用碳-叔丁氧基hydr时，螺为NH产物。杂环化学杂志，46，231（2009）。
• Crystal design, spectroscopic analyses and antibacterial study of new carbazate ligands and their Cu(II) complexes
  作者：Eduardo de A. Duarte、Mariana B. Santiago、Nagela B.S. Silva、Carlos H.G. Martins、Claudia C. Gatto

  DOI：10.1016/j.ica.2023.121421

  日期：2023.5