4-苄基-2-苯基-4H-1,3-噻唑-5-酮 | 22963-07-1

• 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
• 中文名称: 4-苄基-2-苯基-4H-1,3-噻唑-5-酮
• 英文名称: 4-benzyl-2-phenylthiazol-5(4H)-one
• 英文别名: 4-benzyl-2-phenylthiazolone；4-benzyl-2-phenyl-4H-thiazol-5-one；4-Benzyl-2-phenyl-4H-thiazol-5-on；2-Phenyl-4-benzylthiazolin-5-one；4-benzyl-2-phenyl-4H-1,3-thiazol-5-one
• CAS: 22963-07-1
• 化学式: C₁₆H₁₃NOS
• 分子量: 267.351
• InChiKey: DVLLTPNSYDQAED-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  416.8±28.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-苄基-2-苯基-4H-1,3-噻唑-5-酮 在 potassium permanganate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 36.33h， 生成 (Z)-4-benzylidene-2-phenylthiazol-5(4H)-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：

  N-thiobenzoyl-phenylalanine 在 三氟乙酸 作用下， 生成 4-苄基-2-苯基-4H-1,3-噻唑-5-酮
  参考文献：
  名称：

  Konopinska,D. et al., Roczniki Chemii, 1973, vol. 47, p. 35 - 42

  摘要：

  DOI：

文献信息

• Asymmetric catalytic alkynylation of thiazolones and azlactones for synthesis of quaternary α-amino acid precursors
  作者：Beibei Meng、Qian Shi、Yuan Meng、Jie Chen、Weiguo Cao、Xiaoyu Wu

  DOI：10.1039/d1ob00582k

  日期：——

  Asymmetric alkynylation of thiazolones and azlactones with alkynylbenziodoxolones as the electrophilic alkyne source catalyzed by thiourea phosphonium salt is described. By using thiazolones as nucleophiles, the desired alkyne functionalized thiazolones were obtained in 55–89% yields with 31–86% ee. Azlactones gave the desired products in comparable yields with lower enantioselectivities. Ring-opening

  描述了硫脲鏻盐催化的噻唑酮和吖内酯的不对称炔基化反应，其中炔基苯并氧唑酮作为亲电炔烃源。通过使用噻唑酮作为亲核试剂，以 55-89% 的产率和 31-86% 的 ee 获得所需的炔烃官能化噻唑酮。Azlactones 以较低的对映选择性以相当的产率得到所需的产物。炔基化产物的开环导致α，α-二取代的α-氨基酸衍生物有效而不会损失对映选择性。
• Trifluoroacetic acid as a cyclisation reagent for the synthesis of thiazol-5(4H)-ones and 2-thiazolines
  作者：G. C. Barrett、A. R. Khokhar

  DOI：10.1039/j39690001117

  日期：——

  The title compounds are obtained by cyclisation with trifluoroacetic acid of N-thiobenzoyl-α-amino-acids and 2-thiobenzamidoalkanols, respectively.

  通过分别用N-硫代苯甲酰基-α-氨基酸和2-硫代苯甲酰胺基链烷醇的三氟乙酸环化获得标题化合物。
• Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones
  作者：Joyce Z. Crich、Rosario Brieva、Peer Marquart、Rui Lin Gu、Steffen Flemming、Charles J. Sih

  DOI：10.1021/jo00064a010

  日期：1993.6

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.
• On the Tautomerism of 2,4-Disubstituted Thiazolones
  作者：Yuhui Lin、Kenneth K. Andersen

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

  日期：2002.2
• Dakin-West Reaction of N-Thioacylprolines Using Trifluoroacetic Anhydride: Novel Access to 5-Trifluoromethylthiazoles
  作者：Masami Kawase、Yuri Hagimoto、Ryosuke Saijo

  DOI：10.3987/com-13-12904

  日期：——

  The reaction between N-thioacylprolines and trifluoro acetic anhydride in the presence of pyridine afforded a good yield of 5-trifluoromethylthiazoles. This reaction proceeded through mesoionic 1,3-thiazolium-5-olates, followed by cleavage of the pyrrolidine ring and the formation of thiazoles, introducing a trifluoromethyl group at position 5 in the thiazole ring.