Methyl 4-[(2-oxo-4-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoate | 890604-89-4

• 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 4-[(2-oxo-4-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoate
• CAS: 890604-89-4
• 化学式: C₁₂H₉NO₃S₂
• 分子量: 279.34
• InChiKey: YQEWVSSEEWAWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  降冰片烯 、 Methyl 4-[(2-oxo-4-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoate 在 对苯二酚 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以70%的产率得到9-(4-(methyloxycarboxy)phenyl)-3,7-dithia-5-azatetracyclo[9.2.1.0^2,10.0^4,8]tetradec-4(8)-en-6-one
  参考文献：
  名称：

  Investigation of anticancer and anti-parasitic activity of thiopyrano[2,3-d]thiazoles bearing norbornane moiety

  摘要：

  DOI：

  10.7124/bc.00094f
• 作为产物：
  描述：

  4-硫代噻唑烷-2-酮 、 对甲酰基苯甲酸甲酯 在 溶剂黄146 作用下， 反应 0.33h， 生成 Methyl 4-[(2-oxo-4-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]benzoate
  参考文献：
  名称：

  Crotonic, cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction and related tandem processes

  摘要：

  Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54-86% yields via hetero-Diels Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2-thiazolidinones with crotonic, propiolic, and cynnamic acids derivatives. Stereo- and regioselectivity of cycloaddition were investigated. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.083

文献信息

• Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids
  作者：Andrii Lozynskyi、Viktoria Zasidko、Dmytro Atamanyuk、Danylo Kaminskyy、Halyna Derkach、Olexandr Karpenko、Volodymyr Ogurtsov、Roman Kutsyk、Roman Lesyk

  DOI：10.1007/s11030-017-9737-8

  日期：2017.5

  AbstractHere it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(\(5R,6S,7R\))-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and \(\upbeta \)-aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder

  抽象的这里描述了新型rel-（\（5R，6S，7R \））-6-苯甲酰基-7-苯基-2-氧代-3,5,6,7-四氢-的合成，抗氧化剂和抗菌活性的测定2 H-硫代吡喃并[2，3 - d ]噻唑-5-羧酸。通过区域-和非对映选择性的杂-Diels-Alder反应，从5-芳叉基-4-硫代-2--2-噻唑烷酮和\（upbeta \）-芳酰基丙烯酸以高收率获得了目标化合物。通过NMR光谱证实了环加成的立体化学。进行抗氧化和抗菌活性筛选，鉴定出7种化合物（3c，3e，3f，3g，3k，3l，3p）具有高水平的自由基清除能力（43-77％DPPH测定），以及对金黄色葡萄球菌，枯草芽孢杆菌和白色念珠菌有显着影响的化合物（MIC 3.13-6.25 \（\ upmu \ hbox g / mL} \）），但对大肠杆菌有轻微影响。 图形概要
• Investigation of anticancer and anti-parasitic activity of thiopyrano[2,3-d]thiazoles bearing norbornane moiety
  作者：A. P. Kryshchyshyn、D. V. Atamanyuk、D. V. Kaminskyy、Ph. Grellier、R. B. Lesyk

  DOI：10.7124/bc.00094f

  日期：2017.6.30
• Crotonic, cynnamic, and propiolic acids motifs in the synthesis of thiopyrano[2,3-d][1,3]thiazoles via hetero-Diels–Alder reaction and related tandem processes
  作者：Nataliya Zelisko、Dmytro Atamanyuk、Olexandr Vasylenko、Andriy Bryhas、Vasyl Matiychuk、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.tet.2013.11.083

  日期：2014.1

  Various novel thiopyrano[2,3-d][1,3]thiazol-2-one-6-carboxylic acids derivatives were synthesized in 54-86% yields via hetero-Diels Alder reactions and related acylation-based tandem processes of 5-arylidene-4-thioxo-2-thiazolidinones with crotonic, propiolic, and cynnamic acids derivatives. Stereo- and regioselectivity of cycloaddition were investigated. (C) 2013 Elsevier Ltd. All rights reserved.