(E)-N'-benzylidene-2-methylbenzohydrazide | 65349-27-1

• 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: (E)-N'-benzylidene-2-methylbenzohydrazide
• 英文别名: 2-methyl-benzoic acid benzylidenehydrazide；o-Toluylsaeure-benzalhydrazid；2-Methyl-benzoesaeure-benzylidenhydrazid；Benzaldehyd-o-toluylhydrazon；N-[(E)-benzylideneamino]-2-methylbenzamide
• CAS: 65349-27-1
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: OGPWPXOUEMTHSD-LFIBNONCSA-N

物化性质

• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N'-benzylidene-2-methylbenzohydrazide 在 lead dioxide 作用下， 以 溶剂黄146 为溶剂， 反应 0.67h， 以67%的产率得到2-(2-甲基苯基)-5-苯基-1,3,4-恶二唑
  参考文献：
  名称：

  Milcent, Rene; Barbier, Geo, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 77 - 80

  摘要：

  DOI：
• 作为产物：
  描述：

  邻甲基苯甲酸甲酯 在 一水合肼 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (E)-N'-benzylidene-2-methylbenzohydrazide
  参考文献：
  名称：

  Modulation of estrogen-related receptors subtype selectivity: Conversion of an ERRβ/γ selective agonist to ERRα/β/γ pan agonists

  摘要：

  Estrogen Related Receptors (ERRs) are key regulators of energy homeostasis and play important role in the etiology of metabolic disorders, skeletal muscle related disorders, and neurodegenerative diseases. Among the three ERR isoforms, ERR alpha emerged as a potential drug target for metabolic and neurodegenerative diseases. Although ERR beta/gamma selective agonist chemical tools have been identified, there are no chemical tools that effectively target ERR alpha agonism. We successfully engineered high affinity ERR alpha agonism into a chemical scaffold that displays selective ERR beta/gamma agonist activity (GSK4716), providing novel ERR alpha/beta/gamma pan agonists that can be used as tools to probe the physiological roles of these nuclear receptors. We identified the structural requirements to enhance selectivity toward ERR alpha. Molecular modeling shows that our novel modulators have favorable binding modes in the LBP of ERR alpha and can induce conformational changes where Phe328 that originally occupies the pocket is dislocated to accommodate the ligands in a rather small cavity. The best agonists up-regulated the expression of target genes PGC-1 alpha and PGC-1 beta, which are necessary to achieve maximal mitochondrial biogenesis. Moreover, they increased the mRNA levels of PDK4, which play an important role in energy homeostasis.

  DOI：

  10.1016/j.bioorg.2020.104079

文献信息

• Unsaturated compounds containing nitrogen. Part 4. Further reactions of 1-chloro-2,3-diazabutadienes with S-nucleophiles
  作者：William T. Flowers、John F. Robinson、David R. Taylor、Anthony E. Tipping

  DOI：10.1039/p19810000349

  日期：——

  1-Chloro-1,4-diaryl-2,3-diazabutadienes (Ar1CClNNCHAr2), prepared by the reaction of thionyl chloride with aroylhydrazones (Ar1CONHNCHAr2), react with thiosemicarbazide or thiocarbohydrazide to give 2-arylidenehydrazino-5-aryl-1,3,4-thiadiazoles, and with potassium thiocyanate to give 1-thiocyanato-1,4-diaryl-2,3-diaza-butadienes which isomerize thermally to arylideneamino-5-aryl-1,3,4-thiadiazoles

  通过亚硫酰氯与芳酰肼（Ar 1 CONHN CHAr 2）反应制得的1-Chloro-1,4-diaryl-2,3-diazabutadienes（Ar 1 CCl NN CHAr 2）与硫代氨基脲或硫代碳酰肼反应生成2-亚芳基肼基-5-芳基-1,3,4-噻二唑，并与硫氰酸钾反应生成1-硫氰酸根-1,4-二芳基-2,3-二氮杂-丁二烯，其热异构化为芳基氨基-5-芳基-1,3 ，4-噻二唑。1-氯-1,4-二苯基-2,3-二氮杂丁二烯与乙基黄原酸钾反应生成1-乙基黄蒽基-2,3-二氮杂丁二烯，经热解后生成2,5-二苯基-1,3,4-噻二唑。
• The synthesis of <i>N</i>,<i>N</i>′-disulfanediyl-bis(<i>N</i>′-((<i>E</i>)-benzylidene)acetohydrazide) from (<i>E</i>)-<i>N</i>′-benzylideneacetohydrazide and S₈
  作者：Hong-Yan Liu、Yu Chen、Li-Qiang Hao、Guo-Dong Wang、Hong-Shuang Li、Cheng-Cai Xia

  DOI：10.1039/d0ra08441g

  日期：——

  Herein we report an oxidative coupling reaction for N–S/S–S bond formation from (E)-N′-benzylideneacetohydrazide and S8 to furnish substituted N,N′-disulfanediyl-bis(N′-((E)-benzylidene) acetohydrazide). It provides a direct approach for the synthesis of disulfides with good yields.

  在此，我们报道了由 ( E ) -N '-亚苄基乙酰肼和 S 8形成 N-S/S-S 键的氧化偶联反应，以提供取代的N , N '-二硫基-双( N '-(( E ) -亚苄基) 乙酰肼)。它为以良好收率合成二硫化物提供了直接方法。
• Stolle; Stevens, Journal fur praktische Chemie (Leipzig 1954), 1904, vol. <2> 69, p. 378
  作者：Stolle、Stevens

  DOI：——

  日期：——
• MILCENT, R.;BARBIER, G., J. HETEROCYCL. CHEM., 1983, 20, N 1, 77-80
  作者：MILCENT, R.、BARBIER, G.

  DOI：——

  日期：——
• Milcent, Rene; Barbier, Geo, Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 77 - 80
  作者：Milcent, Rene、Barbier, Geo

  DOI：——

  日期：——