(S)-5,5-dimethyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester | 55771-72-7

• 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: (S)-5,5-dimethyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester
• 英文别名: S,N-phenylmethanylylidene-D-penicillamine methyl ester；(S)-5,5-Dimethyl-2-phenyl-4,5-dihydro-thiazol-4-carbonsaeure-methylester；methyl (4S)-5,5-dimethyl-2-phenyl-4H-1,3-thiazole-4-carboxylate
• CAS: 55771-72-7
• 化学式: C₁₃H₁₅NO₂S
• 分子量: 249.334
• InChiKey: RJEFVUNCKUZKDX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5,5-dimethyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 28.0h， 生成 (5R)-3,3-dimethyl-7-oxo-6c-(2-phenoxy-acetylamino)-5-phenyl-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid methyl ester
  参考文献：
  名称：

  Preparation and properties of 5-phenylphenoxymethylpenicillin

  摘要：

  Cycloaddition of azidoacetyl chloride to benzyl D-5,5-dimethyl-5-phenyl-2-thiazoline-4-carboxylate (1a) gave 5-phenyl-6alpha-azidopenicillanate (2a). By catalytic reduction of 2a and reaction with phenoxyacetyl chloride, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester (4a) was obtained. Oxidation of 4a gave the sulfoxide 6, which was isomerized in the presence of DBN. The sulfoxide 7 with the normal configuration could be isolated but deoxygenation of the sulfoxide was not successful. Isomerization of 4a with DBN, either with or without silylation of the side chain, gave a mixture from which 5-phenylphenoxymethylpenicillin benzyl ester (5) was isolated. Compound 5 was debenzylated to 5-phenylphenoxymethylpenicillin potassium salt (8). The antibacterial activity of 8 was low, whereas the 6-epimer 9 was inactive. Contary to published information, the 5-phenylpenam derivative 4c could be prepared by the same method.

  DOI：

  10.1021/jm00239a009
• 作为产物：
  描述：

  苯甲亚胺酸乙酯盐酸盐 、 甲基3-巯基-D-缬氨酸酯盐酸盐 在 二氯甲烷 、 三乙胺 作用下， 生成 (S)-5,5-dimethyl-2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  The Synthesis of Substituted Penicillins and Simpler Structural Analogs. III. Phthalimido β-Lactam-Thiazolidines Derived from Penicillamine

  摘要：

  DOI：

  10.1021/ja01153a099

文献信息

• The Synthesis of Substituted Penicillins and Simpler Structural Analogs. III. Phthalimido β-Lactam-Thiazolidines Derived from Penicillamine
  作者：John C. Sheehan、H. Wayne Hill、Emmett L. Buhle

  DOI：10.1021/ja01153a099

  日期：1951.9
• Preparation and properties of 5-phenylphenoxymethylpenicillin
  作者：Hubert Vanderhaeghe、Jozef Thomis

  DOI：10.1021/jm00239a009

  日期：1975.5

  Cycloaddition of azidoacetyl chloride to benzyl D-5,5-dimethyl-5-phenyl-2-thiazoline-4-carboxylate (1a) gave 5-phenyl-6alpha-azidopenicillanate (2a). By catalytic reduction of 2a and reaction with phenoxyacetyl chloride, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester (4a) was obtained. Oxidation of 4a gave the sulfoxide 6, which was isomerized in the presence of DBN. The sulfoxide 7 with the normal configuration could be isolated but deoxygenation of the sulfoxide was not successful. Isomerization of 4a with DBN, either with or without silylation of the side chain, gave a mixture from which 5-phenylphenoxymethylpenicillin benzyl ester (5) was isolated. Compound 5 was debenzylated to 5-phenylphenoxymethylpenicillin potassium salt (8). The antibacterial activity of 8 was low, whereas the 6-epimer 9 was inactive. Contary to published information, the 5-phenylpenam derivative 4c could be prepared by the same method.