2,2'-[(1E)-3-甲基-1-三氮烯-1,3-二基]二苯甲腈 | 29588-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 2,2'-[(1E)-3-甲基-1-三氮烯-1,3-二基]二苯甲腈
• 英文名称: (S)-5-benzyl-3-phenyl-2-thioxoimidazolidin-4-one
• 英文别名: 5-benzyl-3-phenyl-2-thioxoimidazolidin-4-one；(5S)-5-benzyl-3-phenyl-2-sulfanylideneimidazolidin-4-one
• CAS: 29588-07-6
• 化学式: C₁₆H₁₄N₂OS
• 分子量: 282.366
• InChiKey: HIDCDSHFIITFOM-AWEZNQCLSA-N

物化性质

• 熔点：
  189-190 °C
• 沸点：
  410.6±28.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,2'-[(1E)-3-甲基-1-三氮烯-1,3-二基]二苯甲腈 在 lithium aluminium tetrahydride 、 四氯化钛 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.75h， 生成 (2R,3S)-1-[(5S)-5-benzyl-3-phenyl-2-sulfanylideneimidazolidin-1-yl]-3-(4-methoxyanilino)-2-methyl-3-phenylpropan-1-one
  参考文献：
  名称：

  Investigation of the diastereoselective Mannich reaction using imidazolidin-2-thione as a chiral auxiliary

  摘要：

  Titanium mediated asymmetric Mannich reactions using imidazolidin-2-thione as a chiral auxiliary proceeded in good yields and with high diastereoselectivity to afford the anti-products in the presence of PPh3 additive. A non-chelated transition state with the PPh3-bound titanium enolate was proposed to explain the stereochemistry of the product. Alcoholysis of the adducts with methanol cleaved the imidazolidin-2-thione auxiliary to give the methyl esters in good yields and with excellent ee values. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.008
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2,2'-[(1E)-3-甲基-1-三氮烯-1,3-二基]二苯甲腈
  参考文献：
  名称：

  Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins

  摘要：

  A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.041

文献信息

• 1-(Methyldithiocarbonyl)imidazole as Thiocarbonyl Transfer Reagent: A Facile One-Pot Three-Component Synthesis of 3,5- and 1,3,5-Substituted-2-Thiohydantoins
  作者：H. Ila、G. Sundaram、C. Venkatesh、H. Junjappa

  DOI：10.1055/s-2007-967987

  日期：2007.2

  therapeutics 2 as well as fungicides and herbicides. 3 They have also been used widely for the sequence analy- sis of polypeptides and proteins (Edman degradation). 4 These compounds are usually prepared by reaction of amino acids or amino acid esters with an isothiocyanate. 5 A few of the 2-thiohydantoins have been synthesized by reaction of amino acids with dithiocarbamate esters. 6 We have recently

  已经报道了使用容易获得的氨基酸酯、伯胺和 1-（甲基二硫代羰基）咪唑作为硫代羰基转移试剂的 3,5- 和 1,3,5- 取代的 2-硫代乙内酰脲的高效三组分一锅法合成. 乙内酰脲及其 2-硫代类似物代表了一类重要的杂环，显示出广泛的生物（抗惊厥、抗心律失常、抗毒蕈碱、抗神经、抗癌）活性。1 2-乙内酰脲衍生物在有机合成中也发挥着重要作用，尤其是作为制备合成中间体的原料，具有广泛的治疗作用 2 以及杀真菌剂和除草剂。3 它们也被广泛用于多肽和蛋白质的序列分析（Edman 降解）。4 这些化合物通常通过氨基酸或氨基酸酯与异硫氰酸酯反应制备。5 一些 2-硫代乙内酰脲是通过氨基酸与二硫代氨基甲酸酯的反应合成的。6 我们最近 7 报道了 1-（甲基二硫代羰基）咪唑作为有用的硫代羰基转移试剂的合成应用 8 用于在温和且简单的无危险条件下合成对称和不对称的单、二和三取代硫脲和二硫代氨基甲酸酯。反应条件
• Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light‐Mediated Antibacterial Activity
  作者：Martín S. Faillace、Ana P. Silva、Antonio L. Alves Borges Leal、Luciana Muratori da Costa、Humberto M. Barreto、Walter J. Peláez

  DOI：10.1002/cmdc.202000048

  日期：2020.5.19

  analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light-mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light-enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV-A (400-320 nm) light

  具有不同环外取代基的咪唑啉衍生物可以简单地从常见的起始原料制备。该程序以环保的方式进行。这些衍生物的抗氧化活性通过不同的实验测定方法进行了探索，例如ABTS。+和DPPH。清除测定以及降低功率测定。根据结果​​讨论结构差异。含硫类似物显示出比其含氧同类物更高的抗氧化活性。在微生物学研究中观察到了相同的趋势，其中分析了相同的咪唑啉化合物对金黄色葡萄球菌和大肠杆菌菌株的光介导活性。暴露于UV-A（400-320 nm）光后，几乎所有硫酸化的咪唑啉均观察到光增强活性。
• New functionalized 8-hydroxyquinoline-5-sulfonic acid mesoporous silica (HQS-SBA-15) as an efficient catalyst for the synthesis of 2-thiohydantoin derivatives
  作者：Vaezeh Fathi Vavsari、Ghodsi Mohammadi Ziarani、Saeed Balalaie、Arezoo Latifi、Mehdi Karimi、Alireza Badiei

  DOI：10.1016/j.tet.2016.07.034

  日期：2016.9

  Mesoporous silica SBA-15 functionalized with 8-hydroxyquinoline-5-sulfonic acid (HQS-SBA-15) was used as a new recyclable nanocatalyst for the one-pot synthesis of 2-thiohydantoin derivatives under solvent-free conditions. The catalyst exhibited excellent recyclability at least for 3 times with a high catalytic activity.

  使用8-羟基喹啉-5-磺酸（HQS-SBA-15）功能化的介孔二氧化硅SBA-15作为一种新型可回收纳米催化剂，用于在无溶剂条件下一锅合成2-硫代乙内酰脲衍生物。该催化剂至少具有3次优异的可再循环性，并具有高催化活性。
• Simple and Efficient Synthesis of 5-Substituted-3-phenyl-2-thioxoimidazolidin-4-one Derivatives from<i>S</i>-Amino Acids and Phenylisothiocyanate in Et₃N/DMF-H₂O
  作者：Asha D. Jangale、Yogesh B. Wagh、Yogesh A. Tayade、Dipak S. Dalal

  DOI：10.1080/00397911.2015.1052506

  日期：2015.8.18

  A concise approach for the transformation of various S-amino acids into the 5-alkyl-3-phenyl-2-thioxoimidazolidin-4-one heterocycles using phenylisothiocyanate is described. Phenylthiohydantoins of amino acid were synthesized at room temperature in Et3N/DMF-H2O with easy workup and excellent yields.
• Microwave-assisted traceless synthesis of thiohydantoin
  作者：Mei-Jung Lin、Chung-Ming Sun

  DOI：10.1016/j.tetlet.2003.09.156

  日期：2003.11

  An efficient, microwave-assisted method for the liquid-phase combinatorial synthesis of 3,5-disubstituted-thiohydantoin has been developed. Fmoc-protected amino acids were coupled with HO-PEG-OH and after deprotection, reacted with various isothiocyanates in microwave cavity. The PEG bound thiourea compounds underwent base mediated cyclization/cleavage step by microwave flash heating. The desired products were then liberated from the soluble matrix in good yield and purity under microwave exposure. (C) 2003 Elsevier Ltd. All rights reserved.