methyl (2Z)-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolidin-5-ylidene]acetate | 66628-63-5

• 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: methyl (2Z)-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolidin-5-ylidene]acetate
• 英文别名: methyl (Z)-2-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetate；methyl (Z)-2-[4-oxo-3-phenyl-2-(phenylimino)thiazolidin-5-ylidene]acetate；((Z)-4-oxo-3-phenyl-2-(Ξ)-phenylimino-thiazolidin-5-ylidene)-acetic acid methyl ester；methyl (2Z)-2-(4-oxo-3-phenyl-2-phenylimino-1,3-thiazolidin-5-ylidene)acetate
• CAS: 66628-63-5
• 化学式: C₁₈H₁₄N₂O₃S
• 分子量: 338.387
• InChiKey: ZPSGVSOKCIKALB-XXBNJKRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N'-二苯基硫脲 以 甲苯 、 乙腈 为溶剂， 反应 1.17h， 生成 methyl (2Z)-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolidin-5-ylidene]acetate
  参考文献：
  名称：

  5-亚烷基和5-亚氨基取代的若丹宁衍生物的制备及其抗氧化和抗菌活性的新方法

  摘要：

  通过Wittig反应，从α-二氧噻唑系统和膦烷中报道了5-亚氨基或5-亚亚甲基取代的1，3-噻唑烷-4-酮衍生物的多功能合成。评价了化合物的抗微生物和抗氧化活性。5-羰基亚甲基取代的2-thioxo-1,3-thiazolidines具有比5-arilimino取代的抗氧化剂更好的抗氧化性能。在相同浓度下，化合物3的％抑制值（90.8％）接近于标准BHT（93.6％）。在1，3-噻唑烷环的C-5位具有亚烷基-酰胺基的化合物5和15在合成的化合物中显示出最高的抗菌活性。

  DOI：

  10.1016/j.tet.2015.04.069

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。
• Addition reactions of heterocyclic compounds. Part 74. Products from dimethyl acetylenedicarboxylate with thiourea, thioamide, and guanidine derivatives
  作者：R. Morrin Acheson、John D. Wallis

  DOI：10.1039/p19810000415

  日期：——

  in acetonitrile gave a fused thiazolidinone derivative, but in methanol a fused thiazinone was obtained. Structures were assigned to adducts from other thioureas by comparison with the 13C n.m.r. spectra for these compounds. A method has been developed for distinguishing between the possible structural types of adducts for guanidine and amidine derivatives with DMAD using 1H and 13C n.m.r. spectroscopy

  将苯并咪唑-2-硫酮与乙炔二甲酸二甲酯（DMAD）在乙腈中混合，得到稠合的噻唑烷酮衍生物，但在甲醇中，得到了稠合的噻嗪酮。通过与这些化合物的13 C nmr光谱比较，将结构分配给其他硫脲的加合物。已开发出一种使用1 H和13 C nmr光谱技术来区分DMAD与胍和am衍生物的加合物可能的结构类型的方法。从各种硫代酰胺和DMAD的产物通过其核磁共振谱和其他光谱进行鉴定。
• An efficient solvent-tuning approach for the rapid synthesis of thiazolidinone derivatives and the selective synthesis of 2-amino-4H-1,3-thiazin-4-one and dimethyl 3,3′-thiodiacrylates
  作者：Garima Choudhary、Rama Krishna Peddinti

  DOI：10.1016/j.tetlet.2014.08.032

  日期：2014.10

  Green synthetic approach has been developed for the rapid generation of thiazolidinone derivatives as crystallized products under catalyst-free conditions in water by polarity adjustment with ethyl lactate as a co-solvent in excellent yields. Additionally, interesting findings on the synthesis of 2-amino-4H-1,3-thiazin-4-one and dimethyl 3,3'-thiodiacrylates have been reported. (C) 2014 Elsevier Ltd. All rights reserved.
• One-Pot Stereoselective Synthesis of Alkyl (<i>Z</i>)-2-[4-Oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetates from Acetylenic Esters and N, N′ -Diphenylthiourea
  作者：Monireh Heshmati Gonbari、Ali Ramazani、Ali Souldozi

  DOI：10.1080/10426500802111488

  日期：2009.2.3

  N, N' -diphenylthiourea reacts with dialkyl acetylenedicarboxylates in acetone to form 1:1 adducts, which undergo a cyclization reaction to produce alkyl (Z)-2-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetates in fairly good yields. NMR spectra indicated that the reaction is completely stereoselective.
• A new method for the preparation of 5-acylidene and 5-imino substituted rhodanine derivatives and their antioxidant and antimicrobial activities
  作者：Şevket Hakan Üngören、Sevil Albayrak、Ahmet Günay、Lutfiye Yurtseven、Nurgül Yurttaş

  DOI：10.1016/j.tet.2015.04.069

  日期：2015.6

  Versatile syntheses of 5-imino or 5-acylidene substituted 1,3-thiazolidin-4-one derivatives are reported from α-dioxothiazole systems and phosphoranes via Wittig reactions. Antimicrobial and antioxidant activity of the compounds were evaluated. 5-Carbonylmethylene substituted 2-thioxo-1,3-thiazolidines have better antioxidant properties than the 5-arylimino substituted ones. The % inhibition value

  通过Wittig反应，从α-二氧噻唑系统和膦烷中报道了5-亚氨基或5-亚亚甲基取代的1，3-噻唑烷-4-酮衍生物的多功能合成。评价了化合物的抗微生物和抗氧化活性。5-羰基亚甲基取代的2-thioxo-1,3-thiazolidines具有比5-arilimino取代的抗氧化剂更好的抗氧化性能。在相同浓度下，化合物3的％抑制值（90.8％）接近于标准BHT（93.6％）。在1，3-噻唑烷环的C-5位具有亚烷基-酰胺基的化合物5和15在合成的化合物中显示出最高的抗菌活性。