5-methylthio-2-phenyloxazol-4-yltriphenylphosphonium iodide | 70615-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-methylthio-2-phenyloxazol-4-yltriphenylphosphonium iodide
• 英文别名: (5-methylsulfanyl-2-phenyl-oxazol-4-yl)-triphenyl-phosphonium; iodide；[5-(Methylsulfanyl)-2-phenyl-1,3-oxazol-4-yl](triphenyl)phosphanium iodide；(5-methylsulfanyl-2-phenyl-1,3-oxazol-4-yl)-triphenylphosphanium;iodide
• CAS: 70615-81-5
• 化学式: C₂₈H₂₃NOPS*I
• 分子量: 579.441
• InChiKey: AZVWBBMEVMSBQB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methylthio-2-phenyloxazol-4-yltriphenylphosphonium iodide 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以83%的产率得到5-methylthio-2-phenyloxazole
  参考文献：
  名称：

  yl-甜菜碱，2-苯基-2-恶唑啉-5-酮衍生物及其硫代和硒代类似物的结构和性质

  摘要：

  化学，光谱和X射线的综合结构研究表明，当羰基氧原子被硫或硫取代时，含有5-氧代-2-苯基-4-恶唑烷部分的三聚体三苯基phosph基化物的结构和性质发生相当大的变化。硒。与O> S> Se系列的电负性降低相反，这种取代导致内酯结构的贡献明显减少，甜菜碱结构的重要性增加，但与这些双键形成的不同能力有关。元素。硫代或硒代羰基使叶立德位点失活已应用于区域选择性合成。

  DOI：

  10.1016/0040-4020(94)01041-w
• 作为产物：
  描述：

  1-benzoylamino-2,2-dichloroethenyltriphenylphosphonium chloride 在 sodium hydrogensulfide 作用下， 以 甲醇 为溶剂， 反应 33.0h， 生成 5-methylthio-2-phenyloxazol-4-yltriphenylphosphonium iodide
  参考文献：
  名称：

  Lobanov, O. P.; Martynyuk, A. P.; Drach, B. S., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1816 - 1824

  摘要：

  DOI：

文献信息

• In silico and in vitro studies of a number PILs as new antibacterials against MDR clinical isolate <i>Acinetobacter baumannii</i>
  作者：Maria M. Trush、Vasyl Kovalishyn、Diana Hodyna、Olexandr V. Golovchenko、Svitlana Chumachenko、Igor V. Tetko、Volodymyr S. Brovarets、Larysa Metelytsia

  DOI：10.1111/cbdd.13678

  日期：2020.6

  AbstractQSAR analysis of a set of previously synthesized phosphonium ionic liquids (PILs) tested against Gram‐negative multidrug‐resistant clinical isolate Acinetobacter baumannii was done using the Online Chemical Modeling Environment (OCHEM). To overcome the problem of overfitting due to descriptor selection, fivefold cross‐validation with variable selection in each step of the model development was applied. The predictive ability of the classification models was tested by cross‐validation, giving balanced accuracies (BA) of 76%–82%. The validation of the models using an external test set proved that the models can be used to predict the activity of newly designed compounds with a reasonable accuracy within the applicability domain (BA = 83%–89%). The models were applied to screen a virtual chemical library with expected activity of compounds against MDR Acinetobacter baumannii. The eighteen most promising compounds were identified, synthesized, and tested. Biological testing of compounds was performed using the disk diffusion method in Mueller‐Hinton agar. All tested molecules demonstrated high anti‐A. baumannii activity and different toxicity levels. The developed classification SAR models are freely available online at http://ochem.eu/article/113921 and could be used by scientists for design of new more effective antibiotics.
• Brovarets, V. S.; Lobanov, O.P.; Drach, B. S., Journal of general chemistry of the USSR, 1983, vol. 53, # 9, p. 1819 - 1823
  作者：Brovarets, V. S.、Lobanov, O.P.、Drach, B. S.

  DOI：——

  日期：——
• Drach,B.S. et al., Journal of general chemistry of the USSR, 1979, vol. 49, p. 622 - 623
  作者：Drach,B.S. et al.

  DOI：——

  日期：——
• Lobanov, O. P.; Martynyuk, A. P.; Drach, B. S., Journal of general chemistry of the USSR, 1980, vol. 50, p. 1816 - 1824
  作者：Lobanov, O. P.、Martynyuk, A. P.、Drach, B. S.

  DOI：——

  日期：——
• Structure and properties of phosphonium ylides-betaines, derivatives of 2-phenyl-2-oxazolin-5-one and its thio- and seleno-analogues
  作者：Luc Van Meervelt、Geertrui S. Schuerman、Vladimir S. Brovarets、Nikolai I. Mishchenko、Evgenii A. Romanenko、Boris S. Drach

  DOI：10.1016/0040-4020(94)01041-w

  日期：1995.1

  investigation has shown that the structure and properties of mesomeric triphenylphosphonium ylides containing the 5-oxo-2-phenyl-4-oxazolidene moiety undergo considerable changes when the carbonyl oxygen atom is replaced by sulfur or selenium. This substitution leads to a clear decrease of the contribution of the ylide structure and an increased importance of the betaine structure, in contradiction with

  化学，光谱和X射线的综合结构研究表明，当羰基氧原子被硫或硫取代时，含有5-氧代-2-苯基-4-恶唑烷部分的三聚体三苯基phosph基化物的结构和性质发生相当大的变化。硒。与O> S> Se系列的电负性降低相反，这种取代导致内酯结构的贡献明显减少，甜菜碱结构的重要性增加，但与这些双键形成的不同能力有关。元素。硫代或硒代羰基使叶立德位点失活已应用于区域选择性合成。