ethyl (2S)-4-hydroxy-2-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]butanoate | 1260396-05-1

• 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
• 英文名称: ethyl (2S)-4-hydroxy-2-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]butanoate
• CAS: 1260396-05-1
• 化学式: C₁₃H₁₆N₄O₃S
• 分子量: 308.361
• InChiKey: NGRIQFGOHOEJGD-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.28
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.17
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  反式-4-氧基-2-丁烯酸乙酯 、 1-苯基-5-巯基四氮唑 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 苯甲酸 、 sodium tetrahydroborate 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 94.0h， 生成 ethyl (2R)-4-hydroxy-2-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]butanoate 、 ethyl (2S)-4-hydroxy-2-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]butanoate
  参考文献：
  名称：

  5-Mercaptotetrazoles as Synthetic Equivalents of Nitrogen-Contaning Functional Groups. The Case of the Organocatalytic Enantioselective aza-Michael Reaction

  摘要：

  5-Mercaptotetrazoles have been identified as useful and versatile Michael donors in enantioselective amine-catalyzed aza-Michael reactions with alpha,beta-unsaturated aldehydes, showing excellent behavior as N-nucleophiles instead of their usual trend to react as S-nucleophiles. In addition several unprecedented chemical modifications on the tetrazolothione moiety have been carried out leading to the enantioselective preparation of different compounds incorporating nitrogen-containing functionalities such as oxazinimines, formamidines, ureas and isoureas.

  DOI：

  10.1021/ol102892f