(3R)-3-[4-(4-methoxyphenyl)-5-thioxo-1H-tetrazol-1-yl]pentan-1-ol | 1260396-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3R)-3-[4-(4-methoxyphenyl)-5-thioxo-1H-tetrazol-1-yl]pentan-1-ol
• 英文别名: 1-[(3R)-1-hydroxypentan-3-yl]-4-(4-methoxyphenyl)tetrazole-5-thione
• CAS: 1260396-07-3
• 化学式: C₁₃H₁₈N₄O₂S
• 分子量: 294.378
• InChiKey: KGHGBLLLWLJCIC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-3-[4-(4-methoxyphenyl)-5-thioxo-1H-tetrazol-1-yl]pentan-1-ol 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 20.0 ℃ 、607.99 kPa 条件下， 反应 108.0h， 生成 (3R,e)-methyl N-1-(tert-butyldiphenylsilyloxy)pentan-3-yl-N'-(4-methoxyphenyl)carbamimidate
  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
• 作为产物：
  描述：

  反式-2-戊烯醛 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 sodium tetrahydroborate 、 苯甲酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 94.0h， 生成 (3R)-3-[4-(4-methoxyphenyl)-5-thioxo-1H-tetrazol-1-yl]pentan-1-ol
  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