5-((3S,5S)-5-methylpyrrolidin-3-yl)-1H-tetrazole | 1004750-53-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-((3S,5S)-5-methylpyrrolidin-3-yl)-1H-tetrazole
• 英文别名: 5-[(3S,5S)-5-methylpyrrolidin-3-yl]-2H-tetrazole
• CAS: 1004750-53-1
• 化学式: C₆H₁₁N₅
• 分子量: 153.187
• InChiKey: ZSIRYDZCPWIPMM-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl (2S,4S)-2-methyl-4-(1H-tetrazol-5-yl)pyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到5-((3S,5S)-5-methylpyrrolidin-3-yl)-1H-tetrazole
  参考文献：
  名称：

  Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions:  Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol

  摘要：

  The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with a-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the beta-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.

  DOI：

  10.1021/ja074907+