para-(methoxy)benzoyl(thiobenzoyl)methane | 76525-84-3

• 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
• 英文名称: para-(methoxy)benzoyl(thiobenzoyl)methane
• 英文别名: 1-(4-Methoxyphenyl)-3-phenyl-3-sulfanylidenepropan-1-one
• CAS: 76525-84-3
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: VXYMWCKMZDSCOM-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±51.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯化铋 、 para-(methoxy)benzoyl(thiobenzoyl)methane 在 sodium acetate 作用下， 以 甲醇 为溶剂， 生成 tris(para-(methoxy)benzoyl-thiobenzoyl-methanato-O,S) bismuth(III)
  参考文献：
  名称：

  Synthesis and molecular structure of tris(benzoyl-thiobenzoyl-methanato-O,S) bismuth(III)

  摘要：

  The title bismuth(III) complexes, Bi[C6H5C(S)CHC(O)C6H4-X]3 (X = H, OMe, Cl in para position) have been synthesized and characterized. The crystal and molecular structure of the complex Bi[C6H5C(S)CHC(O)C6H5]3 has been determined. It crystallizes in the triclinic space group P1BAR. The molecule associates to a loosely held dimer through a weak Bi-S interaction forming a highly asymmetrical four-membered Bi2S2 bridge structure.

  DOI：

  10.1016/s0277-5387(00)86932-6
• 作为产物：
  描述：

  Thiobenzoic acid O-ethyl ester 、 对甲氧基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以72.1%的产率得到para-(methoxy)benzoyl(thiobenzoyl)methane
  参考文献：
  名称：

  Bismuth(iii) β-thioxoketonates as antibiotics against Helicobacter pylori and as anti-leishmanial agents

  摘要：

  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 [Bi{R1C(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 [Bi{C5H4NC(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。

  DOI：

  10.1039/c3dt52544a

文献信息

• Saini, S. K.; Gupta, V. D.; Mehrotra, R. C., Journal of the Indian Chemical Society, 1982, vol. 59, # 11/12, p. 1424 - 1426
  作者：Saini, S. K.、Gupta, V. D.、Mehrotra, R. C.

  DOI：——

  日期：——
• 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。
• Synthesis and molecular structure of tris(benzoyl-thiobenzoyl-methanato-O,S) bismuth(III)
  作者：Anil K. Mishra、Vishnu D. Gupta、Gerald Linti、Heinrich Nöth

  DOI：10.1016/s0277-5387(00)86932-6

  日期：1992.1

  The title bismuth(III) complexes, Bi[C6H5C(S)CHC(O)C6H4-X]3 (X = H, OMe, Cl in para position) have been synthesized and characterized. The crystal and molecular structure of the complex Bi[C6H5C(S)CHC(O)C6H5]3 has been determined. It crystallizes in the triclinic space group P1BAR. The molecule associates to a loosely held dimer through a weak Bi-S interaction forming a highly asymmetrical four-membered Bi2S2 bridge structure.