N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester | 59834-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester
• 英文别名: ethyl carbazone of o-hydroxyacetophenone；ethyl N-[1-(2-hydroxyphenyl)ethylideneamino]carbamate
• CAS: 59834-04-7
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: IEXXMWVQEHFCIW-UHFFFAOYSA-N

物化性质

• 熔点：
  144 °C
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester 在 氯化亚砜 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 2-(甲硫基)-1-苯并呋喃
  参考文献：
  名称：

  炔硫醇盐的亲核分子内环化反应

  摘要：

  2-（邻羟基苯基）-alkynethiolates和-selenolates，通过碱催化的环切割得到的4-（邻-羟基苯基）-1,2,3-噻二唑和1,2,3- selenadiazoles，顺利转化为2-苯并呋喃硫醇盐和-硒醇盐。这些反应性中间体可以高产率烷基化。该反应序列可以用于合成富电子的硫杂冠醚。2-（邻-氨基苯基）-炔硫醇类似地形成2-甲基磺酰亚胺基。

  DOI：

  10.1016/s0040-4020(00)00315-x
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 肼基甲酸乙酯 以 乙醇 为溶剂， 生成 N'-[1-(2-hydroxy-phenyl)-ethylidene]-hydrazinecarboxylic acid ethyl ester
  参考文献：
  名称：

  摘要：

  Following the Hurd-Mori procedure, 4-(2-hydroxyaryl)-1,2,3-thiadiazoles were synthesized from o-hydroxyacetophenones. Treatment of the products with bases gives 2-benzofuranthiolates which can be involved in alkylation and arylation reactions.

  DOI：

  10.1023/a:1022568808446

文献信息

• Nucleophilic Intramolecular Cyclization Reactions of Alkynechalcogenolates
  作者：M.A. Abramov、W. Dehaen、B. D'hooge、M.L. Petrov、S. Smeets、S. Toppet、M. Voets

  DOI：10.1016/s0040-4020(00)00315-x

  日期：2000.6

  4-(ortho-hydroxyphenyl)-1,2,3-thiadiazoles and -1,2,3-selenadiazoles, smoothly transform into 2-benzofuranthiolates and -selenolates. These reactive intermediates can be alkylated in high yield. This reaction sequence could be applied to the synthesis of electron rich thiacrown ethers. The 2-(ortho-aminophenyl)-alkynethiolate analogously forms 2-methylsulfanylindole.

  2-（邻羟基苯基）-alkynethiolates和-selenolates，通过碱催化的环切割得到的4-（邻-羟基苯基）-1,2,3-噻二唑和1,2,3- selenadiazoles，顺利转化为2-苯并呋喃硫醇盐和-硒醇盐。这些反应性中间体可以高产率烷基化。该反应序列可以用于合成富电子的硫杂冠醚。2-（邻-氨基苯基）-炔硫醇类似地形成2-甲基磺酰亚胺基。
• Synthesis of benzo[b]furan-2-thioles from 4-(2-hydroxyaryl)-1,2,3-thiadiazoles
  作者：M. L. Petrov、M. Iekhlev、F. S. Teplyakov、D. A. Androsov

  DOI：10.1134/s1070428012050168

  日期：2012.5

  4-(2-Hydroxyaryl)-1,2,3-thiadiazoles treated with bases decompose with nitrogen liberation and the formation of benzo[b]furan-2-thiolates. On acidifying the thiolates benzo[b]furan-2-thiols were obtained. 4-(4- and -5-Benzyloxy-2-hydroxyphenyl)-1,2,3-thiadiazoles formed analogously the corresponding benzo[b]furan-2-thiolates whose acidifying afforded polymeric compounds.
• The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors
  作者：Anna Minkkilä、Mikko J. Myllymäki、Susanna M. Saario、Joel A. Castillo-Melendez、Ari M.P. Koskinen、Christopher J. Fowler、Jukka Leppänen、Tapio Nevalainen

  DOI：10.1016/j.ejmech.2009.01.007

  日期：2009.7

  A series of para-substituted phenolic N-alkyl carbamates were evaluated for their FAAH and MGL inhibitory activities. The compounds were generally selective for FAAH, with IC50 values in the nM range, whereas inhibition of MGL required concentrations three orders of magnitude higher. The most potent compounds, dodecylcarbamic acid 4-(4,5-dihydrothiazol-2-yl)phenyl (12) and 4-(1,2,3-thiadiazol-4-yl)phenyl (26) esters, inhibited FAAH and MGL with IC50 values at the low-nanomolar (IC(50)s: 0.0063 and 0.012 mu M) and the low-micromolar ranges (IC(50)s; 2.1 and 1.0 mu M), respectively. Compound 26 also inhibited both FAAH-dependent AEA uptake and AEA hydrolysis (IC50; 0.082 mu M) by intact RBL2H3 cells, and could also reduce 2-AG hydrolysis by these cells at concentrations >= 0.030 mu M. (C) 2009 Elsevier Masson SAS. All rights reserved.
• ——
  作者：M. L. Petrov、W. Dehaen、M. A. Abramov、I. P. Abramova、D. A. Androsov

  DOI：10.1023/a:1022568808446

  日期：——

  Following the Hurd-Mori procedure, 4-(2-hydroxyaryl)-1,2,3-thiadiazoles were synthesized from o-hydroxyacetophenones. Treatment of the products with bases gives 2-benzofuranthiolates which can be involved in alkylation and arylation reactions.