5-(2-hydroxybenzylidene)rhodanine | 34709-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(2-hydroxybenzylidene)rhodanine
• 英文别名: 5-(2-hydroxybenzylidene)-2-thioxothiazolidin-4-one；[2-Hydroxy-benzyliden]-rhodanin；5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 34709-44-9
• 化学式: C₁₀H₇NO₂S₂
• mdl: MFCD00186339
• 分子量: 237.303
• InChiKey: ZROKEZLWNZKNSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  218-220 °C (decomp)(Solv: acetic acid (64-19-7))
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxybenzylidene)rhodanine 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 0.03h， 生成 4-Hydrazono-5-[1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-thiazolidine-2-thione
  参考文献：
  名称：

  Dabholkar, Vijay V.; Ahmed, Syed Sagir, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2646 - 2649

  摘要：

  DOI：
• 作为产物：
  描述：

  罗丹宁 、 水杨醛 在 2-氨基乙醇,甲酸 作用下， 反应 0.1h， 以91%的产率得到5-(2-hydroxybenzylidene)rhodanine
  参考文献：
  名称：

  A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid

  摘要：

  2-Hydroxyethylammonium formate 作为一种任务特异性离子液体 (TSIL)，可用于羰基化合物与罗丹宁的 Knoevenagel 缩合反应，从而在无溶剂条件下获得芳基亚烷基罗丹宁，而且收率极高。此外，与有机溶剂相比，在我们的离子液体（IL）存在下获得的产率显著提高。本研究还首次报道了 TSIL 催化作用的详细机理。

  DOI：

  10.1139/v10-011

文献信息

• trans -Aconitic acid-based hetero -Diels-Alder reaction in the synthesis of thiopyrano[2,3- d ][1,3]thiazole derivatives
  作者：Nataliya Zelisko、Olexandr Karpenko、Volodymyr Muzychenko、Andrzej Gzella、Philippe Grellier、Roman Lesyk

  DOI：10.1016/j.tetlet.2017.03.062

  日期：2017.5

  hetero-Diels-Alder reaction of 5-arylideneisorhodanines with trans-aconitic acid proceeds as a regio- and diastereoselective process with spontaneous decarboxylation of the [4+2]-adduct to furnish thiopyrano[2,3-d][1,3]thiazole (2) and chromeno[4′,3′:4,5]thiopyrano[2,3-d]thiazole (3) derivatives analogously to the use of itaconic acid as a dienophile. Conversely, the one-pot, three-component reaction of 5-ar

  5-芳基异二十二碳四烯酸与反式-乌头酸的异-狄尔斯-阿尔德反应是区域和非对映选择性过程，其中[4 + 2]加合物自发脱羧生成噻喃并[2,3- d ] [1,3类似于使用衣康酸作为亲双烯体，]噻唑（2）和苯并[4'，3'：4,5]巯基吡喃并[2,3- d ]噻唑（3）衍生物。相反，5-arylideneisorhodanines，一锅，三组分反应反式-aconitic酸和苯胺进行时没有脱羧，从而导致新的相对- （5' - [R，6' - [R，7' - [R）-5'-羧基7'-芳基的1-芳基-3'，7'-二氢-2 ħ，2 ' ħ，5 ħ -螺[吡咯烷3,6'噻喃并[2,3- d ]噻唑] -2,2'，5-三酮4。有趣的是，使用的反式导致区域选择性相反-aconitic羧酸三甲酯，得到的rel - （5 - [R，6小号，7小号）-5- methyloxycarbonylmethyl -2-氧代-7-芳基-3
• Synthesis, molecular modeling, selective aldose reductase inhibition and hypoglycemic activity of novel meglitinides
  作者：Manar G. Salem、Yasmine M. Abdel Aziz、Marwa Elewa、Mohamed S. Nafie、Hosam A. Elshihawy、Mohamed M. Said

  DOI：10.1016/j.bioorg.2021.104909

  日期：2021.6

  In the present study, a novel generation of selective aldose reductase ALR2 inhibitors with significant hypoglycemic activities was designed and modulated based on rhodanine scaffold joined to an acetamide linker in between two lipophilic moieties. The synthesis of the novel compounds was accomplished throughout simple chemical pathways. Molecular docking was performed on B-cell membrane protein SUR1

  在本研究中，设计并调节了具有显着降血糖活性的新一代选择性醛糖还原酶 ALR2 抑制剂，其基础是在两个亲脂性部分之间连接到乙酰胺接头的罗丹宁支架。新化合物的合成是通过简单的化学途径完成的。在B细胞膜蛋白 SUR1、醛还原酶 ALR1 和醛糖还原酶 ALR2 活性位点上进行分子对接。化合物10B、11B、12B、15C、16C、26F和27F显示出最高的降血糖活性，血糖水平分别降低了 80.7、85.2、87、82.3、83.5、81.4 和 85.3%。它们比标准降血糖药瑞格列奈更有效，血糖水平降低 65.4%。IC 50 0.29 和 0.35 µM 的化合物12B和15C比 IC 50 0.40 µM的标准 ALR2 抑制剂依帕司他更有效。它们对 ALR2 的选择性分别超过 ALR1 134 和 116 倍。分子对接研究与体外和体内结果相匹配，以阐明化合物12B和15C的双重活性 作为 ALR2
• A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid
  作者：Abdolhamid Alizadeh、Mohammad M. Khodaei、Ali Eshghi

  DOI：10.1139/v10-011

  日期：2010.6

  2-Hydroxyethylammonium formate acts as a task-specific ionic liquid (TSIL) for the Knoevenagel condensation of carbonyl compounds with rhodanine to afford arylalkylidene rhodanines under solvent-free conditions and in good-to-excellent yields. Additionally, compared with those in organic solvents, the yields obtained in the presence of our ionic liquid (IL) were significantly increased. The detailed mechanism of the catalytic effect of TSIL is also reported for the first time.

  2-Hydroxyethylammonium formate 作为一种任务特异性离子液体 (TSIL)，可用于羰基化合物与罗丹宁的 Knoevenagel 缩合反应，从而在无溶剂条件下获得芳基亚烷基罗丹宁，而且收率极高。此外，与有机溶剂相比，在我们的离子液体（IL）存在下获得的产率显著提高。本研究还首次报道了 TSIL 催化作用的详细机理。
• Facile Synthesis of 5‐Benzylidene Rhodamine Derivatives under Microwave Irradiation
  作者：Jian‐Feng Zhou、Yuan‐Zhi Song、Feng‐Xia Zhu、Yu‐Lan Zhu

  DOI：10.1080/00397910600941166

  日期：2006.11.1

  Abstract A series of 5‐benzylidenerhodamine derivatives were synthesized by the cross‐aldol condensation of an aromatic aldehyde with rhodamine or rhodamine acetic acid in sodium acetate/acetic acid under microwave irradiation. The reaction was completed in 8–20 min with 63–94% yields and was environmentally benign with easy workup.

  摘要 通过芳香醛与罗丹明或罗丹明醋酸在醋酸钠/醋酸中在微波辐射下发生交叉羟醛缩合反应，合成了一系列 5-亚苄基罗丹明衍生物。反应在 8-20 分钟内完成，产率为 63-94%，对环境无害，易于处理。
• Synthesis, structure analysis, investigation of conductivity, thermal properties of polyphenol derivatives containing a rhodanine moiety and their Cu(II), VO(IV) complexes
  作者：İsmet Kaya、Ayşe Erçağ、Süleyman Çulhaoğlu

  DOI：10.1016/j.ica.2020.119642

  日期：2020.8

  In this study, 5-benzylidenerhodanine derivatives namely 5-(2-hydroxybenzylidene)-2-thioxothiazolidin-4-one (SAR) and 5((2-hydroxynaphthalen-1-yl)methylene)-2-thioxothiazolidin-4-one (HNAR) used as monomer. The new polymers of SAR and HNAR (PSAR and PHNAR respectively) were synthesized by oxidative polycondensation reaction. The polymers were characterized by elemental, FT-IR, UV-Vis, H-1 NMR,C- 13 NMR, TG-DTA analyses techniques. The molecular weight distribution values of the PSAR and PHNAR were determined by size exclusion chromatography (SEC) analysis. According to the SEC analyses, the number average molecular weight (M-n), weight average molecular weight (M-w) and polydispersity index (PDI) values of PSAR and PHNAR were found to be 5300, 7250 g mol(-1) and 1.368; 5750, 7350 g mol(-1) and 1.278, respectively. The Cu (II), VO (IV) complexes of PSAR and PHNAR (PSAR-Cu and PSAR-VO) were successfully prepared using Cu (AcO)(2)xH(2)O and VOSO(4)x5H(2)O hydrate salts. The polymer-metal-complexes were characterized by FT-IR, elemental and TG-DTA analysis techniques. The weight losses of PHNAR, PHNAR-Cu, PHNAR-VO, PSAR, PSAR-Cu and PSAR-VO were found to be 69.50, 58.50, 62.25, 89.05, 74.55 and 61.75% at 1000 degrees C, respectively. TG analyses were showed to be stable of synthesized polymers against thermal decomposition. Electrical properties of doped polymers, undoped polymers and their complexes were determined. Also, the optical band gaps (Eg) of these complexes were calculated from their absorption edges.