(3-methyl-4H-benzo[b][1,4]thiazin-2-yl)(phenyl)methanone | 60290-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (3-methyl-4H-benzo[b][1,4]thiazin-2-yl)(phenyl)methanone
• 英文别名: (3-methyl-4H-1,4-benzothiazin-2-yl)(phenyl)methanone；3-Methyl-4H-benzo[b][1,4]thiazin-2-ylphenylmethanone；2-benzoyl-1-methyl-3-phenyl-1H-1,4-benzothiazine；2-benzoyl-3-methyl-4H-1,4-benzothiazine；(3-methyl-4H-benzo[1,4]thiazin-2-yl)-phenyl-methanone；2-Benzoyl-3-methyl-4H-1,4-benzothiazin；Methanone, (3-methyl-4H-1,4-benzothiazin-2-yl)phenyl-；(3-methyl-4H-1,4-benzothiazin-2-yl)-phenylmethanone
• CAS: 60290-49-5
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: YRYFKYZRXINQER-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184 °C(Solv: ethanol (64-17-5))
• 沸点：
  389.4±42.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-methyl-4H-benzo[b][1,4]thiazin-2-yl)(phenyl)methanone 以94%的产率得到
  参考文献：
  名称：

  MINA, ISKANDER, G.;EL, SKIEK, EL, KHAWAD, I.;YOUSIF, G.;FISHER, K. J.;FAI+, GAZZ. CHIM. ITAL., 1985, 115, N 12, 669-675

  摘要：

  DOI：
• 作为产物：
  描述：

  benzoylacetone 以 乙醇 为溶剂， 生成 (3-methyl-4H-benzo[b][1,4]thiazin-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Alyea, Elmer C.; Malek, Abdul, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1325 - 1327

  摘要：

  DOI：

文献信息

• Graphene oxide (GO): An efficient carbocatalyst for the benign synthesis of functionalized 1,4-benzothiazines
  作者：Suchandra Bhattacharya、Pranab Ghosh、Basudeb Basu

  DOI：10.1016/j.tetlet.2017.01.068

  日期：2017.3

  Graphene oxide (GO) has been found to be highly efficient and recyclable carbocatalyst for the benign construction of heterocyclic molecule 1,4-benzothiazine from 2-aminothiophenol and 1,3-dicarbonyl compound. A vast range of highly functionalized 1,4-benzothiazine derivatives has been synthesized constituting a general and sustainable protocol. It is proposed that the large surface area of GO nanosheet

  已经发现氧化石墨烯（GO）是用于由2-氨基硫酚和1,3-二羰基化合物良性构建杂环分子1,4-苯并噻嗪的高效且可回收的碳催化剂。合成了广泛的高度官能化的1,4-苯并噻嗪衍生物，构成了一般且可持续的方案。提出GO纳米片的大表面积以及在边缘，基面和插入层上存在的酸性和氧化基团的存在有效地催化了氧化环化。
• Baker's yeast catalyzed synthesis of 1,4-benzothiazines, performed under ultrasonication
  作者：Umesh R. Pratap、Dhanaji V. Jawale、Balaji S. Londhe、Ramrao A. Mane

  DOI：10.1016/j.molcatb.2010.09.018

  日期：2011.1

  An efficient and simple one pot method has been developed for the synthesis of 1,4-benzothiazines by allowing the condensation of 2-aminobenzenethiols and 1,3-dicarbonyls using cheaper biocatalyst, baker's yeast. The role of ultrasonication in the rate expediting of the condensation has been discussed.

  已经开发出一种有效且简单的一锅法，用于合成1，4-苯并噻嗪，方法是使用较便宜的生物催化剂面包酵母使2-氨基苯硫醇和1,3-二羰基化合物缩合。讨论了超声在加速缩合速率中的作用。
• One-Pot Multi-Component Approach to the Synthesis of 1,4-Benzothiazines in Aqueous Media
  作者：Hassan Sheibani、Mohammad Reza Islami、Avid Hassanpour、Kazem Saidi

  DOI：10.1080/10426500701544599

  日期：2007.12.24

  strategy for the oxidative cyclocondensation of 2-aminobenzenethiol and 1,3-dicarbonyls has been developed in order to obtain 2,3-disubstituted 1,4-benzothiazines at ambient temperature and in aqueous media. A mechanism is presented to account for the formation of the products.

  为了在环境温度和水性介质中获得 2,3-二取代的 1,4-苯并噻嗪，已经开发了一种新的快速合成策略，用于 2-氨基苯硫醇和 1,3-二羰基的氧化环缩合。提出了一种机制来解释产品的形成。
• Novel synthesis of 1,4-benzothiazines in water accelerated by β-cyclodextrin
  作者：Balaji S. Londhe、Sudhakar L. Padwal、Manisha R. Bhosale、Ramrao A. Mane

  DOI：10.1007/s13738-015-0752-3

  日期：2016.3

  Novel one-pot synthetic protocol has been developed for obtaining 2, 3-disubstituted 1,4-benzothiazines with excellent yields, carrying cyclocondensation of 1,3-dicarbonyl compounds with substituted 2-(2-(2-aminophenyl)disulfanyl)benzenamines, under supramolecular catalysis of β-Cyclodextrin (β-CD) in water at neutral pH. The role of β-CD in accelerating the cyclocondensation has been demonstrated. This biomimic catalyzed route is simple, economic, relatively rapid and environmentally benign.

  已经开发出一种新颖的一锅合成方法，用于高效制备2, 3-二取代的1, 4-苯并噻嗪，该方法涉及在β-环糊精（β-CD）的超分子催化下，中性pH值的水相中，将1, 3-二羰基化合物与取代的2-(2-(2-氨基苯基)二硫醚)苯胺进行环缩合反应。研究表明，β-CD在加速环缩合反应中发挥了作用。这种仿生催化途径简单、经济、相对快速且环境友好。
• Ligandenaustauschreaktionen von NiCl₂ (PPh₃)₂ mit O(S)⌒N⌒S-Liganden / Ligand Exchange Reactions of NiCl₂(PPh₃)₂ with O(S )⌒ N ⌒ S Ligands
  作者：Stefan Sawusch、Uwe Schilde

  DOI：10.1515/znb-1999-0710

  日期：1999.7.1

  Ligand exchange reactions of NiCl₂(PPh₃)₂ with O (S )⌒N⌒S ligands were studied. Oxidation products of O⌒N⌒S ligands have been characterized and their structures determined: 3-methyl-4H-benzo[b] [ 1,4]thiazin-2-yl-phenylmethanone / 2-methyl-benzo[d] [ 1,3]thiazole (mixed crystal); [2-iminoisopropyl-thiophenolato(2-)](triphenyl-phosphane)-nickel(II); 1 -phenyl-3-methyl-4-(benzoyl-thiobenzoylhydrazono)-pyrazol-5-thione; [ 1 -phenyl-3-methyl- 4-(benzoyl-thiobenzoylhydrazono)-pyrazol-5-thionato](triphenyl-phosphane)-nickel(II).

  NiCl₂(PPh₃)₂与O(S)⌒N⌒S配体的配体交换反应已经研究。O⌒N⌒S配体的氧化产物已经表征并确定了它们的结构：3-甲基-4H-苯并[b][1,4]噻二唑-2-基苯甲酮/2-甲基-苯并[d][1,3]噻唑（混合晶体）；[2-亚胺异丙硫酚基(2-)](三苯基膦)-镍(II)；1-苯基-3-甲基-4-(苯甲酰硫苯甲酰肼基)-吡唑-5-硫酮；[1-苯基-3-甲基-4-(苯甲酰硫苯甲酰肼基)-吡唑-5-硫代氧基](三苯基膦)-镍(II)。