(3R)-3-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]undecan-1-ol | 1260396-03-9

• 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-phenyl-5-thioxo-1H-tetrazol-1-yl]undecan-1-ol
• CAS: 1260396-03-9
• 化学式: C₁₈H₂₈N₄OS
• 分子量: 348.513
• InChiKey: OEXHSQHYINKMKD-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.87
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R)-3-[4-phenyl-5-thioxo-1H-tetrazol-1-yl]undecan-1-ol 在 盐酸 、 氢气 作用下， 以 水 、 甲苯 为溶剂， 20.0 ℃ 、607.99 kPa 条件下， 反应 72.0h， 以73%的产率得到(4R,Z)-N-(4-octyl-1,3-oxazinan-2-ylidene)aniline
  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-2-十一烯醛 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-phenyl-5-thioxo-1H-tetrazol-1-yl]undecan-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