4,4'-Diisobutyl-[4,4']bithiazolidinyl-2,5,2',5'-tetraone | 199447-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,4'-Diisobutyl-[4,4']bithiazolidinyl-2,5,2',5'-tetraone
• 英文别名: 4-(2-methylpropyl)-4-[4-(2-methylpropyl)-2,5-dioxo-1,3-thiazolidin-4-yl]-1,3-thiazolidine-2,5-dione
• CAS: 199447-97-7
• 化学式: C₁₄H₂₀N₂O₄S₂
• 分子量: 344.456
• InChiKey: NMJIUFZXFWYOIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-Diisobutyl-[4,4']bithiazolidinyl-2,5,2',5'-tetraone 、 甘氨酸乙酯盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以39%的产率得到(3a,6a-Diisobutyl-2,4,6-trioxo-hexahydro-pyrrolo[3,4-d]imidazol-5-yl)-acetic acid ethyl ester
  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：

  2,2'-Diethoxy-4,4'-diisobutyl-4H,4'H-[4,4']bithiazolyl-5,5'-dione 在 盐酸 作用下， 以 苯 为溶剂， 反应 3.0h， 以80%的产率得到4,4'-Diisobutyl-[4,4']bithiazolidinyl-2,5,2',5'-tetraone
  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