3-oxo-4-phenyl-3,4-dihydro-2H-1,4-benzothiazine | 103110-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-oxo-4-phenyl-3,4-dihydro-2H-1,4-benzothiazine
• 英文别名: 4-phenyl-2H-benzo[b][1,4]thiazin-3(4H)-one；4-Phenyl-1,4-benzothiazin-3-one
• CAS: 103110-40-3
• 化学式: C₁₄H₁₁NOS
• 分子量: 241.313
• InChiKey: LWHWOPMOOIONNX-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  479.4±25.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₁₄H₁₁ClINO 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 、 硫代乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 13.25h， 以60%的产率得到3-oxo-4-phenyl-3,4-dihydro-2H-1,4-benzothiazine
  参考文献：
  名称：

  Copper-Catalyzed Cascade Syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and Quinoxalin-2(1H)-ones through Capturing S and N Atom Respectively from AcSH and TsNH₂

  摘要：

  A copper-catalyzed cascade method has been developed to synthesize the 2H-benzo[b][1,4]thiazin-3(4H)-ones from 2-halo-N-(2-halophenyl)-acetamides 1 and AcSH via the S(N)2/deacetylation/coupling process, and to synthesize the quinoxalin-2(1H)-ones from 1 and TsNH2 via the S(N)2/coupling/desulfonation process. The target products were obtained with diversity at three positions on their scaffolds.

  DOI：

  10.1021/jo101253a

文献信息

• Direkte<i>N</i>-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion
  作者：Bernd Renger

  DOI：10.1055/s-1985-31364

  日期：——

  Direct N-Arylation of Amides: An Improvement of the Goldberg-Reaction: The copper-catalyzed N-arylation of amides, the Goldberg reaction, usually requires drastic reaction conditions and produces only moderate yields of the desired products. Much better results can be achieved by modifying the reaction conditions, We used copper on silica as a catalyst and potassium acetate as a base and continuously removed the resulting acetic acid from the reaction mixture. In this way we gained high, in some cases nearly quantitative yields of the arylated or heteroarylated products.

  胺的直接N-芳基化：戈德堡反应的改进：铜催化的胺N-芳基化，即戈德堡反应，通常需要苛刻的反应条件，并且只产生适量的预期产物。通过改进反应条件，可以获得更好的结果。我们使用了硅胶上的铜作为催化剂，以醋酸钾作为碱，并且持续从反应混合物中去除生成的醋酸。通过这种方式，我们获得了高产率，在某些情况下几乎是定量的芳基化或杂芳基化产物。
• Copper-catalyzed one-pot synthesis of 1,4-benzothiazine-3-ones
  作者：Lingyu Zhang、Songlin Zhang

  DOI：10.1016/j.tetlet.2023.154761

  日期：2023.10

  An efficient potassium carbonate and copper-mediated CS and CN Ullmann coupling reaction between 2-bromothiophenol and 2-haloacetanilide is reported here. This protocol affords a simple and efficient approach for the construction of 1,4-benzothiazinone-3-one derivatives, avoiding the limitations of using noble metals and expensive ligands for the first time.

  本文报道了 2-溴苯硫酚和 2-卤代乙酰苯胺之间有效的碳酸钾和铜介导的 C S 和 C N Ullmann 偶联反应。该方案为构建 1,4-苯并噻嗪酮-3-酮衍生物提供了一种简单有效的方法，首次避免了使用贵金属和昂贵配体的限制。
• Expeditious synthesis of C2- or N4-aryl-1,4-benzothiazin-3-one via orthogonal Pd-catalyzed C-arylation and Cu-catalyzed N-arylation
  作者：Wei-Sheng Huang、Rongsong Xu、Rory Dodd、William C. Shakespeare

  DOI：10.1016/j.tetlet.2013.11.053

  日期：2014.1

  Direct, chemo-specific arylation at C-2 or N-4 of 1,4-benzothiazin-3-one with aryl halides, based on Pd or Cu catalyst system, respectively, provided easy entry to arylated derivatives, a class of molecules not easily accessible via existing methods. Under Pd-catalysis conditions with LiHMDS as the base, N-arylation of 1,4-benzothiazin-3-one was inhibited leading to C alpha-arylation of a secondary amide without the need for protection and de-protection of more acidic amido NH. (C) 2013 Elsevier Ltd. All rights reserved.