1,3-双[(4-甲氧基苯基)甲基]硫脲 | 22313-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,3-双[(4-甲氧基苯基)甲基]硫脲
• 英文名称: 1,3-bis(4-methoxyphenylmethyl)thiourea
• 英文别名: N,N-di(4-methoxybenzyl)thiourea；1,3-bis-(4-methoxy-benzyl)-thiourea；N,N'-bis-(4-methoxy-benzyl)-thiourea；N,N'-Bis-(4-methoxy-benzyl)-thioharnstoff；1,3-Bis[(4-methoxyphenyl)methyl]thiourea
• CAS: 22313-70-8
• 化学式: C₁₇H₂₀N₂O₂S
• 分子量: 316.424
• InChiKey: AEVPFOZAPNAKHW-UHFFFAOYSA-N

物化性质

• 熔点：
  151 °C
• 沸点：
  475.6±55.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-双[(4-甲氧基苯基)甲基]硫脲 在 sodium acetate 、 溶剂黄146 、 β-丙氨酸 作用下， 反应 1.0h， 生成 3-(5-((3-(4-methoxybenzyl)-2-(4-methoxybenzylimino)-4-oxothiazolidin-5-ylidene)methyl)furan-2-yl)benzoic acid
  参考文献：
  名称：

  Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships

  摘要：

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.014
• 作为产物：
  描述：

  (E)-4-甲氧基苯甲醛肟 在 sodium amalgam 、 乙醇 、 溶剂黄146 作用下， 生成 1,3-双[(4-甲氧基苯基)甲基]硫脲
  参考文献：
  名称：

  Goldschmidt; Polonowska, Chemische Berichte, 1887, vol. 20, p. 2407

  摘要：

  DOI：

文献信息

• Synthetic studies on 2,4-benzothiazepin-5(1H)-one and 2,4-benzodiazepin-1-one derivatives.
  作者：HIROSHI FUJITA、YASUNOBU SATO

  DOI：10.1248/cpb.23.1764

  日期：——

  2, 4-Benzothiazepin-5 (1H)-one were usually the predominant products in reactions of o-chloromethylbenzoyl chloride with 1, 3-disubstituted thioureas ; but with methyl, benzyl or allyl substituted thioureas, 2, 4-benzodiazepin-1-ones were obtained together with 2, 4-benzothiazepin-5 (1H)-ones. These structures were elucidated from infrared, ultraviolet and nuclear magnetic resonance spectra. We also found that nature of the base and solvent as well as thiourea substituents affected the course of the reactions affording 2, 4-benzothiazepin-5 (1H)-ones or 2, 4-benzodiazepin-1-ones. Several 2, 4-benzothiazepin-5 (1H)-ones and 2, 4-benzodiazepin-1-ones possessed weak pharmacological activities, such as coronary vasodilating and local anesthetic activity.

  2, 4-苯并噻嗪-5(1H)-酮通常是邻氯甲基苯甲酰氯与1,3-双取代硫脲反应中的主要产物；但当硫脲含有甲基、苄基或烯丙基取代基时，会同时得到2, 4-苯并二氮杂䓬-1-酮与2, 4-苯并噻嗪-5(1H)-酮。这些结构通过红外、紫外和核磁共振光谱得以阐明。我们还发现，碱和溶剂的性质以及硫脲的取代基会影响反应的进程，从而生成2, 4-苯并噻嗪-5(1H)-酮或2, 4-苯并二氮杂䓬-1-酮。一些2, 4-苯并噻嗪-5(1H)-酮和2, 4-苯并二氮杂䓬-1-酮具有较弱的药理活性，如冠状动脉舒张和局部麻醉作用。
• 3-methoxybenzyl thiourea derivatives and improved lipid compositions containing same
  申请人：The Fanning Corporation

  公开号：US20020147365A1

  公开（公告）日：2002-10-10

  1-(3-methoxybenzyl)-3-substituted thiourea antioxidant compounds and improved lipids compositions which are supplemented with amounts of such antioxidant compounds effective for augmenting oxidative stability of the base lipid are provided. Also provided are methods for enhancing the oxidative stability of a lipid comprising supplementing a base lipid in need of enhanced oxidative stability with at least one 1-(3-methoxybenzyl)-3-substituted thiourea compound of the present invention.

  提供了一种抗氧化化合物，其为1-(3-甲氧基苄基)-3-取代硫脲，以及通过添加这些抗氧化化合物的有效量来改善脂质组成，从而增强基础脂质的氧化稳定性的方法。还提供了一种增强脂质氧化稳定性的方法，该方法包括向需要增强氧化稳定性的基础脂质中补充至少一种本发明所述的1-(3-甲氧基苄基)-3-取代硫脲化合物。
• Rapid and highly efficient synthesis of thioureas in biocompatible basic choline hydroxide
  作者：Najmedin Azizi、Elham Farhadi

  DOI：10.1080/17415993.2017.1327591

  日期：2017.9.3

  ABSTRACT A straightforward and convenient synthesis of symmetrical thiourea derivatives by the reaction of primary amines and carbon disulfide in biocompatible basic choline hydroxide is presented. A variety of biologically important thiourea derivatives can be obtained in good to excellent yields without a tedious work-up under mild reaction conditions. A series of primary aliphatic and aromatic amines

  摘要介绍了通过伯胺和二硫化碳在生物相容性碱性氢氧化胆碱中的反应直接和方便地合成对称硫脲衍生物。无需在温和的反应条件下进行繁琐的后处理，即可以良好至极好的收率获得多种具有生物学意义的硫脲衍生物。一系列具有不同取代官能团的脂肪族和芳香族伯胺已在较温和的反应条件和较短的反应时间内转化为硫脲衍生物。图形概要
• Convenient Synthesis of 5-Arylidene-2-imino-4-thiazolidinone Derivatives Using Microwave Irradiation
  作者：Emmanuelle Braud、Manal Sarkis、Diem-Ngan Tran、Maria Dasso Lang、Christiane Garbay

  DOI：10.1055/s-0033-1341108

  日期：——

  A concise approach for the preparation of 5-arylidene-2-imino-4-thiazolidinone derivatives is described. Structurally diverse amines, isothiocyanates, aldehydes, and chloroacetyl chloride were combined under microwave irradiation to afford new 5-arylidene-2-imino-4-thiazolidinone derivatives. The one-pot synthesis involves the in situ formation of a thiourea followed by reaction with chloroacetyl chloride

  描述了一种用于制备 5-arylidene-2-imino-4-thiazolidinone 衍生物的简明方法。结构不同的胺、异硫氰酸酯、醛和氯乙酰氯在微波辐射下结合，得到新的 5-亚芳基-2-亚氨基-4-噻唑烷酮衍生物。一锅合成包括硫脲的原位形成，然后与氯乙酰氯和醛反应生成目标化合物。
• 3-Methoxybenzyl thiourea derivatives and improved lipid compositions containing same
  申请人：The Fanning Corporation

  公开号：US20010056205A1

  公开（公告）日：2001-12-27

  1-(3-methoxybenzyl)-3-substituted thiourea antioxidant compounds and improved lipids compositions which are supplemented with amounts of such antioxidant compounds effective for augmenting oxidative stability of the base lipid are provided. Also provided are methods for enhancing the oxidative stability of a lipid comprising supplementing a base lipid in need of enhanced oxidative stability with at least one 1-(3-methoxybenzyl)-3-substituted thiourea compound of the present invention.

  本发明提供了一种1-(3-甲氧基苯基)-3-取代硫脲抗氧化化合物以及含有这种抗氧化化合物的改良脂质组成物，其中这种抗氧化化合物的添加量有效增强了基础脂质的氧化稳定性。同时，本发明还提供了增强脂质氧化稳定性的方法，包括将需要增强氧化稳定性的基础脂质补充至少一种本发明的1-(3-甲氧基苯基)-3-取代硫脲化合物。