N-[1-(3-hydroxyphenyl)ethylideneamino]-4-methylbenzenesulfonamide | 355812-31-6

• 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-(3-hydroxyphenyl)ethylideneamino]-4-methylbenzenesulfonamide
• CAS: 355812-31-6
• 化学式: C₁₅H₁₆N₂O₃S
• 分子量: 304.37
• InChiKey: AVHMEXCCEBQXLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-双三氟甲基溴苯 、 N-[1-(3-hydroxyphenyl)ethylideneamino]-4-methylbenzenesulfonamide 在 bis(triphenylphosphine)palladium(II) dichloride 、 caesium carbonate 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以92%的产率得到3-(1-(3,5-bis(trifluoromethyl)phenyl)vinyl)phenol
  参考文献：
  名称：

  Palladium Catalyzed Coupling of Tosylhydrazones with Aryl and Heteroaryl Halides in the Absence of External Ligands: Synthesis of Substituted Olefins

  摘要：

  Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydroxyl and amine functional groups. This method allows synthesizing a variety of heterocyclic compounds, which are difficult to access from other traditional methods and are not synthesized by employing similar coupling reactions. Application of the present methodology is validated in tandem reaction of ketones to the corresponding substituted olefins in a single pot experiment.

  DOI：

  10.1021/jo301987c
• 作为产物：
  描述：

  3-羟基苯乙酮 、 对甲苯磺酰肼 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以84%的产率得到N-[1-(3-hydroxyphenyl)ethylideneamino]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Palladium Catalyzed Coupling of Tosylhydrazones with Aryl and Heteroaryl Halides in the Absence of External Ligands: Synthesis of Substituted Olefins

  摘要：

  Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydroxyl and amine functional groups. This method allows synthesizing a variety of heterocyclic compounds, which are difficult to access from other traditional methods and are not synthesized by employing similar coupling reactions. Application of the present methodology is validated in tandem reaction of ketones to the corresponding substituted olefins in a single pot experiment.

  DOI：

  10.1021/jo301987c

文献信息

• Palladium‐Catalyzed Ring‐Opening Addition of Activated Vinyl Cyclopropanes with N‐Tosylhydrazones
  作者：Yiding Wang、Lei Shen、Helin Wang、Yixin Luo、Qingle Zeng

  DOI：10.1002/ejoc.202200942

  日期：2023.2.13

  Palladium-catalyzed ring-opening addition reaction of activated vinyl cyclopropanes with N-tosylhydrazones provides N-tosylhydrazone butenylmalonate compounds in good yields. Aromatic aldehyde-derived N-tosylhydrazones produced terminal and internal N-allylated products, in which the terminal products are the main. While ketone-derived tosylhydrazones produced only terminal addition products.

  钯催化的活化乙烯基环丙烷与N-甲苯磺酰腙的开环加成反应以良好的收率提供N-甲苯磺酰腙丁烯基丙二酸酯化合物。芳香醛衍生的N-甲苯磺酰腙产生末端和内部N-烯丙基化产物，其中以末端产物为主。而酮衍生的甲苯磺酰腙只产生末端加成产物。
• Palladium Catalyzed Coupling of Tosylhydrazones with Aryl and Heteroaryl Halides in the Absence of External Ligands: Synthesis of Substituted Olefins
  作者：Devi Prasan Ojha、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo301987c

  日期：2012.12.21

  Palladium catalyzed cross-coupling reaction of hydrazones with aryl halides in the absence of external ligand is reported. The versatility of this coupling reaction is demonstrated in showcasing the selectivity of coupling reaction in the presence of hydroxyl and amine functional groups. This method allows synthesizing a variety of heterocyclic compounds, which are difficult to access from other traditional methods and are not synthesized by employing similar coupling reactions. Application of the present methodology is validated in tandem reaction of ketones to the corresponding substituted olefins in a single pot experiment.