4-phenyl-2-phenylthiazolone | 22962-98-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-phenyl-2-phenylthiazolone
• 英文别名: 2,4-diphenyl-4H-thiazol-5-one；2,4-diphenyl-4H-1,3-thiazol-5-one
• CAS: 22962-98-7
• 化学式: C₁₅H₁₁NOS
• 分子量: 253.324
• InChiKey: GLDHKLDFAGNNLW-UHFFFAOYSA-N

物化性质

• 沸点：
  411.8±48.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-phenylthiazolone 在 potassium permanganate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.33h， 以55%的产率得到4-(5-oxo-2,4-diphenyl-1,3-thiazol-4-yl)-2,4-diphenyl-1,3-thiazol-5-one
  参考文献：
  名称：

  Synthesis of Symmetrical 2,2',4,4'-Tetrasubstituted [4,4'-Bithiazole]-5,5'(4H,4'H)-diones and Their Reactions with Some Nucleophiles.

  摘要：

  Symmetrical 2,2',4,4'-tetrasubstituted-[4,4'-bithiazole]-5,5'(4H,4'H)-diones were obtained in high yields by oxidation of 5(4H)-thiazolones by KMnO4 in acetic acid. In some cases, the isomeric 2.4'- and 2,2'-bithiazolones were also formed. Results from two crossover reactions were consistent with a free radical mechanism. Four series of thiazolones were prepared, each based on a different substituent at the 2-position; i.e., phenyl, ethoxy, ethyl and ethylthio. The effects of substituents on the isomer distributions of the dehydrodimers indicated that electronic factors were less important than steric factors. X-Ray crystallography established the structure of the dehydrodimer (4R*,4'R*)-2,2'-diethoxy-4,4'dibenzyl-[4,4'-bithiazole]-5,5'(4H,4'H)-dione. One stereoisomer of 2,2'diphenyl-4,4'-dimethyl-[4,4'-bithiazole]-5,5'(4H,4'H)-dione and a mixture of the stereoisomers of 2,2'-diphenyl-4,4'-dibenzyl-[4,4'-bithiazole]-5,5'(4H,4'K)-dione were treated with nucleophiles. The former gave imide derivatives of alpha,alpha'-dehydrodimeric amino acids when the nucleophile was L-alanine ethyl ester or I-butylamine. The structure of one of the reaction products, (4R*,5R*)-2,5-diphenyl-2-thiazoline-4-carboxylic acid piperidylamide, was established by X-ray crystallography. Treatment of stereoisomeric mixtures of 2,2'-diethoxy-4,4'-bithiazolones with HCl in benzene gave the corresponding racemic and meso bis-(N-carboxythioanhydride)s. A stereoisomeric mixture of the bis(N-carboxythioanhydride)s of leucine treated with glycine ethyl ester gave a bicyclic derivative of the alpha,alpha'-dehydrodimeric amino acid.

  DOI：

  10.3891/acta.chem.scand.51-1000
• 作为产物：
  描述：

  phenyl-thiobenzoylamino-acetic acid amide 在 三氟乙酸 作用下， 反应 12.0h， 以93%的产率得到4-phenyl-2-phenylthiazolone
  参考文献：
  名称：

  On the Tautomerism of 2,4-Disubstituted Thiazolones

  摘要：

  DOI：

  10.1002/1099-0690(20022)2002:3<557::aid-ejoc557>3.0.co;2-7

文献信息

• Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective Mannich-Type Reaction between Enamides and Thiazolones
  作者：Jun Kikuchi、Norie Momiyama、Masahiro Terada

  DOI：10.1021/acs.orglett.6b00857

  日期：2016.6.3

  An enantioselective Mannich-type reaction between enamides, serving as aliphatic imine equivalents, and thiazolones or an azlactone, serving as α-amino acid derived pronucleophiles, was investigated using a chiral phosphoric acid catalyst. By using thiazolones, Mannich adducts with a tetrasubstituted chiral carbon center at the α-position and an aliphatic substituent at the β-position were efficiently

  使用手性磷酸催化剂研究了作为脂肪族亚胺等同物的酰胺与作为α-氨基酸衍生的亲核试剂的噻唑酮或or内酯之间的对映选择性曼尼希型反应。通过使用噻唑酮，可高效地获得具有高非对映选择性和对映选择性的，在α位具有四取代的手性碳中心且在β位具有脂族取代基的曼尼希加合物。
• Addition reactions of thiazol-5(4H)-ones—II
  作者：G.C. Barrett、R. Walker

  DOI：10.1016/s0040-4020(01)93773-1

  日期：1976.1

  4-substituted 2-phenylthiazol-5(4H)-one and an electron-deficient alkene is shown to include a stable cycloadduct and a Michael adduct formed through the 2- or the 4-position of the thiazolone. The reaction can be diverted towards the Michael adduct entirely, by adding traces of aqueous alkali to the reactants in acetone solution. A novel type of 1:2-adduct is present in the reaction mixture, and is shown to

  在温和条件下在4-取代的2-苯基噻唑-5（4H）-1和缺电子的烯烃之间形成的加合物的混合物显示包括稳定的环加合物和通过2-或4-位形成的Michael加合物噻唑酮。通过在丙酮溶液中向反应物中添加痕量碱金属水溶液，可将反应完全转移至迈克尔加合物。反应混合物中存在一种新型的1：2-加合物，并且显示是通过环加合物与烯烃的反应而形成的。由环加合物挤出羰基硫形成的产物与由类似的恶唑酮和烯烃得到的产物相同，
• Palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with sulfonamido-substituted acyclic allylic carbonates
  作者：Han-Wen Rao、Tian-Lan Zhao、Long Wang、Hong-Dan Deng、Yan-Ping Zhang、Yong You、Zhen-Hua Wang、Jian-Qiang Zhao、Wei-Cheng Yuan

  DOI：10.1039/d3ob01404e

  日期：——

  A palladium-catalyzed decarboxylative α-allylation of thiazolidinones and azlactones with aza-π-allylpalladium zwitterionic intermediates, in situ generated from sulfonamido-substituted allylic carbonates, is successfully developed. This method allows the formation of a series of structurally diverse 5-alkylated thiazolidinones and 2-piperidones under mild conditions in moderate to high yields (up

  成功开发了由磺酰胺基取代的烯丙碳酸酯原位生成的氮杂-π-烯丙基钯两性离子中间体对噻唑烷酮和吖内酯进行钯催化脱羧α-烯丙基化。该方法可以在温和条件下以中等到高产率（高达 99% 的产率）形成一系列结构多样的 5-烷基化噻唑烷酮和 2-哌啶酮。
• BARRETT G. C.; WALKER R., TETRAHEDRON <TETR-AB>, 1976, 32, NO 5, 571-577
  作者：BARRETT G. C.、 WALKER R.

  DOI：——

  日期：——