3-(diphenylthiophosphoryl)-N-phenylbenzenecarbothioamide | 1048667-65-7

• 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: 3-(diphenylthiophosphoryl)-N-phenylbenzenecarbothioamide
• 英文别名: 3-diphenylphosphinothioyl-N-phenylbenzenecarbothioamide
• CAS: 1048667-65-7
• 化学式: C₂₅H₂₀NPS₂
• 分子量: 429.546
• InChiKey: VCVGNGVNQMBREB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(diphenylthiophosphoryl)-N-phenylbenzenecarbothioamide 在 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以54%的产率得到2-[3-(diphenylthiophosphoryl)phenyl]-1,3-benzothiazole
  参考文献：
  名称：

  杂硫代磷酰基-苯并噻唑钯SCN-Pincer配合物：合成和结构修饰对铃木交叉偶联催化性能的影响

  摘要：

  的新颖的混合钳型配体3，6，9，和11，轴承，作为供位点，硫代基和苯并噻唑环的亚胺部分结合的直接向中央苯核或通过O或附连到后者NH接头在与（PhCN）2 PdCl 2（MeCN或PhCN为溶剂，80-120°C）反应的中央苯核的C（2）位置经历直接环palpalladation，得到5,5-和5 6元κ 3 -SCN -钯配合物钳形12 - 15以良好至高产率。仅在N的情况下，用相关的铂前体直接进行环铂电镀才成功-[3-（1，3-苯并噻唑-2-基）苯基] -P，P-二苯基硫代次膦酸酰胺9。将Pd（II）配合物12 - 15被发现是用于一系列与苯基硼酸改变电子芳基溴化物的Suzuki交叉偶联高活性（前）的催化剂。活性最高的复合物14a还有效促进了氯苯乙酮的偶联，在该反应建议的最佳钳形复合物中位居前列。

  DOI：

  10.1021/om101012r
• 作为产物：
  描述：

  (3-Carboxy-phenyl)-diphenyl-phosphinoxid 在 劳森试剂 、 氯化亚砜 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 3-(diphenylthiophosphoryl)-N-phenylbenzenecarbothioamide
  参考文献：
  名称：

  Thiophosphoryl-, Thiophosphoryloxy-, and Thiophosphorylamino-Benzene Derivatives as Novel Classes of Hybrid Pincer Ligands

  摘要：

  The synthetic approaches to novel families of SCE (E = S',N,O) hybrid pincer-type ligands bearing thophosphoryl, thiophosphoryloxy, and thiophosphorylamino groups in various combinations with thiophosphoryl-, thiocarbamoyl-, and imine- (including that of benzothiazole ring) donating functions have been developed. All of the ligands readily undergo direct cyclometallation (metal = Pd(II), Pt(II)) to afford 5,5- or 5,6-membered pincer complexes. Palladium complexes displayed from high to excellent catalytic performance in the Suzuki cross-coupling reaction of aryl bromides and phenylboronic acid and the higher asymmetry for a complex served as a factor of its higher catalytic activity.

  DOI：

  10.1080/10426507.2010.507726

文献信息

• Cyclopalladated Complexes of 3-Thiophosphorylbenzoic Acid Thioamides: Hybrid Pincer Ligands of a New Type. Synthesis, Catalytic Activity, and Photophysical Properties
  作者：V. A. Kozlov、D. V. Aleksanyan、Yu. V. Nelyubina、K. A. Lyssenko、E. I. Gutsul、L. N. Puntus、A. A. Vasil’ev、P. V. Petrovskii、I. L. Odinets

  DOI：10.1021/om8002762

  日期：2008.8.1

  Treatment of the 3-diphenylphosphorylbenzoic acid amides 3a,b with the Lawesson reagent resulted in 3-diphenylthiophosphorylbenzoic acid thioamides 4a,b, which easily underwent cyclopalladation at the C-2 position of the central benzene ring to give new hybrid pincer complexes 5a,b with kappa(3)-SCS coordination. Molecular structures of the complexes were characterized by X-ray diffraction. The peculiarities of chemical bonding in 5a were investigated via topological analysis of charge density in the crystal. The palladium complexes 5a,b demonstrated high catalytic activity for the Suzuki cross-coupling reactions of aryl bromides with phenylboronic acid and exhibited luminescence at 77 and 300 K.