(Z)-2-Methoxycarbonylmethylene-3,4-dihydro-3-oxo-2H-benzo-1,4-thiazine | 37893-72-4

• 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: (Z)-2-Methoxycarbonylmethylene-3,4-dihydro-3-oxo-2H-benzo-1,4-thiazine
• 英文别名: methyl (2Z)-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-ylidene)acetate；2-methoxycarbonylmethylene-3,4-dihydro-2H-1,4-benzothiazine-3-one；methyl 2-(3-oxo-3,4-dihydrobenzo[b][1,4]thiazin-2-ylidene)acetate；2-methoxycarbonylmethylene-3,4-dihydro-2H-1,4-benzthiazin-3-one；((Z)-3-oxo-3,4-dihydro-benzo[1,4]thiazin-2-ylidene)-acetic acid methyl ester；((Z)-3-Oxo-3,4-dihydro-benzo[1,4]thiazin-2-yliden)-essigsaeure-methylester；methyl (2Z)-2-(3-oxo-4H-1,4-benzothiazin-2-ylidene)acetate
• CAS: 37893-72-4
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: MGAINRJZMKQGDQ-TWGQIWQCSA-N

物化性质

• 沸点：
  432.4±45.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-Methoxycarbonylmethylene-3,4-dihydro-3-oxo-2H-benzo-1,4-thiazine 在 乙醇 作用下， 生成 methyl (E)-(3'-oxo-3',4'-dihydro-2'H-1',4'-benzothiazin-2'-ylidene)acetate
  参考文献：
  名称：

  Maki; Suzuki, Chemical and pharmaceutical bulletin, 1972, vol. 20, p. 832

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl (Z)-2-(2-aminophenyl)sulfanylbut-2-enedioate 以86%的产率得到
  参考文献：
  名称：

  LISO G.; TRAPANI G.; BERARDI V.; LATROFA A.; MARCHINI P., J. HETEROCYCL. CHEM., 1980, 17, NO 4, 793-796

  摘要：

  DOI：

文献信息

• Structures of Addition Products of Acetylenedicarboxylic Acid Esters with Various Dinucleophiles. An application of C, H-spin-coupling constants
  作者：Ulrich Vögeli、Wolfgang von Philipsborn、Kuppuswamy Nagarajan、Mohan D. Nair

  DOI：10.1002/hlca.19780610207

  日期：1978.3.8

  Heterocyclic compounds obtained by addition of acetylenedicarboxylic acid esters to thioureas, cyclic amidines and o-difunctionalized aromatic systems have been studied by 13C-NMR. In particular, C, H-spin-coupling constants over two and three bonds were used to differentiate between the various constitutional isomers and to establish the configuration of trisubstituted exocyclic C, C-double bonds

  通过13 C-NMR研究了通过将乙炔二羧酸酯加到硫脲，环am和邻双官能化的芳族体系中得到的杂环化合物。特别地，在两个和三个键上的C，H-自旋偶联常数用于区分各种结构异构体并建立三取代的外环C，C-双键的构型。邻位顺式和反式C，H-spin偶联的构型意义和诊断价值在本系列中再次得到证明。
• Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and <i>o</i>-aminothiophenol
  作者：Ekaterina E Stepanova、Maksim V Dmitriev、Andrey N Maslivets

  DOI：10.3762/bjoc.16.193

  日期：——

  Two synthetic approaches to enaminones fused to 1,4-benzothiazin-2-one moiety, which can be interesting in studies on biological activity, chemosensors, and fluorescence, were developed via the reaction of furan-2,3-diones or acylpyruvic acids in the presence of carbodiimides with o-aminothiophenols. The target enaminones were formed together with pharmaceutically interesting 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones. A selective synthetic approach to 2-hydroxy-2H-1,4-benzothiazin-3(4H)-ones was developed via the solvent-switchable reaction of furan-2,3-diones with o-aminothiophenol. Preliminary biological assays (antimicrobial, acute toxicity) of the new compounds were carried out.

  通过呋喃-2,3-二酮或酰基丙酮酸在碳化二亚胺存在下与邻氨基苯硫酚的反应，我们开发了两种合成融合了 1,4-苯并噻嗪-2-酮分子的烯酰胺酮的方法，这些烯酰胺酮在生物活性、化学传感器和荧光研究方面具有重要意义。目标烯酮与具有药学意义的 2-羟基-2H-1,4-苯并噻嗪-3(4H)-酮一起形成。通过呋喃-2,3-二酮与邻氨基苯硫酚的溶剂切换反应，开发了一种 2-羟基-2H-1,4-苯并噻嗪-3(4H)-酮的选择性合成方法。对新化合物进行了初步的生物检测（抗菌、急性毒性）。
• Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1039/c1gc15701a

  日期：——

  A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis. The regio- and stereo-chemistry of the products were established by IR, NMR and single crystal X-ray analysis.

  提出了一种高效、优雅且简单的过程，用于合成β-氨基丙烯酸酯衍生物和一系列具有生物学及药物活性的苯并杂环化合物，条件极为温和。该方案为已知方法提供了一种有价值的替代方案，并将应用于绿色合成领域。产品的区域和立体化学性质通过红外光谱、核磁共振和单晶X射线分析得以确定。
• 1,4-benzothiazine-2-acetic acid derivatives
  申请人：Sapporo Breweries Limited

  公开号：US05252571A1

  公开（公告）日：1993-10-12

  1,4-Benzothiazine-2-acetic acid derivatives having an excellent aldose reductase inhibitory activity which are useful for the prevention and treatment of diabetic complications, such as diabetic cataract, retinopathy, nephropathy and neuropathy.

  具有优秀醛糖还原酶抑制活性的1,4-苯并噻嗪-2-乙酸衍生物，可用于预防和治疗糖尿病并发症，如糖尿病白内障、视网膜病变、肾病和神经病变。
• Adducts of 2-aminothiophenol with acetylenic nitriles or esters and their conversion into benzothiazoles and/or 1,4-benzothiazines
  作者：Gaetano Liso、Giuseppe Trapani、Vincenza Berardi、Andrea Latrofa、Paolo Marchini

  DOI：10.1002/jhet.5570170435

  日期：1980.6

  The reaction between 2-aminothiophenol 1 and acetylenic nitriles or esters 2a-d leads to the vinyl thio-ethers 3a-d. The conversion of 3 into benzothiazoles 8 and/or 1,4-benzothiazines 9, in boiling dimethyl sulfoxide, has been achieved. A possible pathway involving benzothiazolines 5 as key intermediates is suggested.

  2-氨基硫酚1与炔腈或酯2a-d之间的反应产生乙烯基硫醚3a-d。在沸腾的二甲基亚砜中已经实现了将3转化为苯并噻唑8和/或1，4-苯并噻嗪9。建议可能的途径涉及苯并噻唑啉5作为关键中间体。