1,3-二苯基-3-硫代-1-丙酮 | 1215-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3-二苯基-3-硫代-1-丙酮
• 英文名称: benzoyl(thiobenzoyl)methane
• 英文别名: Monothiodibenzoylmethan；monothiodibenzoylmethane；Thiodibenzoylmethan；1,3-diphenyl-3-thioxopropan-1-one；1-Propanone, 1,3-diphenyl-3-thioxo-；1,3-diphenyl-3-sulfanylidenepropan-1-one
• CAS: 1215-43-6
• 化学式: C₁₅H₁₂OS
• 分子量: 240.326
• InChiKey: CELMQLYNQRJGQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1,3-二苯基-3-硫代-1-丙酮 在 ammonium acetate 、 氧气 、 溶剂黄146 作用下， 反应 7.0h， 以158 mg的产率得到3,5-二苯基异噻唑
  参考文献：
  名称：

  在无金属条件下使用苯乙酮和二硫酯合成 3,5-二取代异硫唑的新方法

  摘要：

  摘要 为了在过渡金属和无催化剂条件下利用容易获得的苯乙酮、二硫酯和 NH4OAc 合成 3,5-二取代和环状异硫唑，设计了一种简便易行的新方案。该策略涉及通过依次形成亚胺，随后分子内环化和空气氧化在一个锅中分别形成连续的 C-N 和 S-N 键的 C=O 和 C=S 功能化。该协议为 3,5-二取代异噻唑提供了一种低成本、用户友好、直接且广泛适用的方法。图形概要

  DOI：

  10.1080/00397911.2020.1748656
• 作为产物：
  描述：

  2,3-二溴代-1,3-二苯基-1-丙酮 在 甲醇 、 硫化氢 、 sodium methylate 作用下， 生成 1,3-二苯基-3-硫代-1-丙酮
  参考文献：
  名称：

  Tornetta; Agnello, Annali di Chimica, 1958, vol. 48, p. 581,585, 586

  摘要：

  DOI：

文献信息

• Synthesis of β-Amino-α,β-unsaturated Ketone Derivatives via Sequential Rhodium-Catalyzed Sulfur Ylide Formation/Rearrangement
  作者：Jun He、Zengming Man、Yinping Shi、Chuan-Ying Li

  DOI：10.1021/acs.joc.5b00521

  日期：2015.5.1

  a Rh(II) catalyst and β-(methylthio)-α,β-unsaturated ketones, 1-sulfonyl-1,2,3-triazoles can be converted into functionalized β-amino-α,β-unsaturated ketones via formation of α-imino rhodium carbene/sulfur ylide and subsequent rearrangement. The products decompose to useful 2-methylthiopyrrole derivatives conveniently in high yield.

  在Rh（II）催化剂和β-（甲硫基）-α，β-不饱和酮的存在下，可以将1-磺酰基-1,2,3-三唑转化为官能化的β-氨基-α，β-不饱和酮通过形成α-亚氨基铑卡宾/叶立德和随后的重排。该产物可方便地以高产率分解为有用的2-甲基硫代吡咯衍生物。
• Thiolan and monothio-β-diketone formation through the use of a nucleo-electrophilic thiating agent
  作者：Robert T. LaLonde

  DOI：10.1039/c39820000401

  日期：——

  While the treatment of chalcone with anhydrous sodium polysulphide in anhydrous ethanol gave 2,4-dibenzoyl-3,5-diphenylthiolan, which was dehydrogenated to the corresponding thiophen for structure confirmation, the same two reactants in anhydrous 1,2-dimethoxyethane gave 1,3-diphenyl-3-thioxopropan-1-one.

  在无水乙醇中用无水多硫化钠处理查尔酮时，得到2,4-二苯甲酰基-3,5-二苯硫基噻吩，将其脱氢为相应的噻吩以确认结构，而在无水1,2-二甲氧基乙烷中的相同两个反应物则得到1， 3-二苯基-3-硫代丙烷-1-酮。
• Bismuth(<scp>iii</scp>) β-thioxoketonates as antibiotics against Helicobacter pylori and as anti-leishmanial agents
  作者：Philip C. Andrews、Victoria L. Blair、Richard L. Ferrero、Peter C. Junk、Lukasz Kedzierski、Roshani M. Peiris

  DOI：10.1039/c3dt52544a

  日期：——

  Nine different β-thioxoketones of general formula R1C(O)CH2C(S)R2 (R1 = C6H5, R2 = C6H5L1; R1 = C6H5, R2 = p-CF3C6H4L2; R1 = p-MeOC6H4, R2 = C6H5L3; R1 = p-MeOC6H4, R2 = p-CF3C6H4L4; R1 = C5H4N, R2 = C6H5L5; R1 = p-IC6H4, R2 = C6H5L6; R1 = C6H5, R2 = p-IC6H4L7; R1 = C6H5, R2 = C10H7L8 and R1 = CH3, R2 = C6H5L9) and their tris-substituted bismuth(III) complexes having the general formula [BiR1C(O)CHC(S)R2}3] were synthesised and fully characterised. The solid state structure of [BiC5H4NC(O)CHC(S)C6H5}3] B5 was determined by crystallography and revealed that the three β-thioxoketonato ligands are bound to bismuth(III) centre in a bidentate fashion through O and S atoms. The bismuth(III) complexes and the corresponding thioxoketones were assessed for their activity against H. pylori. All of the bismuth(III) complexes were highly active against H. pylori having a MIC of greater than or equal to 3.125 μg mL−1, while the free acids were essentially not toxic to the bacteria. The anti-leishmanial activity of all the bismuth(III) β-thioxoketonates and the corresponding free acids were assessed against L. major promastigotes. The toxicity towards human fibroblast cells was also assessed. All of the free β-thioxoketones were selectively toxic to the L. major promastigotes displaying some potential as anti-leishmanial agents. Among these [C6H5C(O)CH2C(S)C6H5] L1 and [C5H4NC(O)CH2C(S)C6H5] L5 showed comparable activity to that of Amphotericin B, killing about 80% of the L. major promastigotes at a concentration of 25 μM (6.0 μg mL−1). The bismuth(III) β-thioxoketonate complexes were toxic to both the L. major promastigotes and fibroblast cells at high concentrations, but gave no improvement in anti-leishmanial activity over the free β-thioxoketones.

  通式为 R1C(O)CH2C(S)R2（R1 = C6H5，R2 = C6H5L1；R1 = C6H5，R2 = p-CF3C6H4L2；R1＝p-MeOC6H4，R2＝C6H5L3； R1＝p-MeOC6H4，R2＝p-CF3C6H4L4； R1＝C5H4N，R2＝C6H5L5； R1＝p-IC6H4，R2＝C6H5L6；R1＝C6H5，R2＝p-IC6H4L7；R1＝C6H5，R2＝C10H7L8 和 R1＝CH3，R2＝C6H5L9）及其通式为 [BiR1C(O)CHC(S)R2}3] 的三取代铋（III）配合物进行了合成和全面表征。通过晶体学方法确定了 [BiC5H4NC(O)CHC(S)C6H5}3] B5 的固态结构，发现三个δ-硫酮配体通过 O 原子和 S 原子以双齿方式与铋（III）中心结合。评估了铋（III）配合物和相应的硫酮酮对幽门螺杆菌的活性。所有铋（III）络合物对幽门螺杆菌都有很高的活性，其 MIC 大于或等于 3.125 δ¼g mLâ1 ，而游离酸对细菌基本上没有毒性。对所有δ-硫酮酸铋（III）和相应游离酸的抗大肠杆菌原虫活性进行了评估。此外，还评估了对人类成纤维细胞的毒性。所有游离的 β-thioxoketone 都能选择性地对 L. major 原虫产生毒性，显示出作为抗利什曼病原体制剂的一些潜力。其中[C6H5C(O)CH2C(S)C6H5] L1和[C5H4NC(O)CH2C(S)C6H5] L5显示出与两性霉素B相当的活性，在浓度为25δ¼M（6.0δ¼g mLâ1）时可杀死约80%的大鼠原虫。在高浓度下，δ-硫酮酸铋（III）络合物对大叶原虫和成纤维细胞都有毒性，但与游离的δ-硫酮相比，抗利什曼病的活性没有提高。
• Indium derivatives of monothio-β-diketones and the X-ray structure of tris[benzoyl(thiobenzoyl)methanato-o,s]indium(<scp>III</scp>)
  作者：Channareddy Sreelatha、Vishnu D. Gupta、Chaitanya K. Narula、Heinrich Nöth

  DOI：10.1039/dt9850002623

  日期：——

  Six-co-ordinated mono-, bis-, and tris-(monothio-β-diketonates) of iridium(III) have been synthesized and character ized. The X-ray crystal structure of the title compound reveals a distorted octahedral geometry with facia I arrangement of the sulphur and oxygen ligand atoms.

  合成并表征了六配位的铱（III）的单，双和三（单硫代-β-二酮）。标题化合物的X射线晶体结构显示出畸变的八面体几何形状，其中硫和氧配体原子以面相I排列。
• Investigations on technetium and rhenium monothio-βdiketonate complexesand x-ray structure of tris(monothiodibenzoylmethanato)technetium(III)
  作者：Giuliano Bandoli、Ulderico Mazzi、Hartmut Spies、Rudolf Münze、Eberhard Ludwig、Erhard Ulheman、Dieter Scheller

  DOI：10.1016/s0020-1693(00)81739-9

  日期：1987.9

  Six-coordinated tris(monothio-β-diketonates) of Tc(III) and Re(III) have been synthesized by the reaction of M(III) thiourea complexes with the appropriate monothio-β-diketone ligands in methanol. Characterization of the compounds by IR, UV-Vis, 1H NMR and mass spectroscopy indicates that the ligands coordinate as bidentate. The 1H NMR spectra of the paramagnetic substances are well resolved and the

  Tc（III）和Re（III）的六配位三（单硫代-β-二酮）（三价）是通过M（III）硫脲络合物与适当的单硫代-β-二酮配体在甲醇中的反应合成的。通过IR，UV-Vis，1 H NMR和质谱对化合物的表征表明，配体作为二齿配位。顺磁性物质的1 H NMR光谱得到很好的解析，螯合环质子显示Tc复合物的大高场频移和相应的Re类似物的低场频移。在三（单硫代二苯甲酰基甲基甲烷）tech（III）上进行的完整晶体和分子结构测定，是具有O和S螯合配体的Tc（III）化合物的首次结构表征。