(5S)-5-((1H-tetrazol-5-yl)methyl)-2,2,3-trimethylimidazolidin-4-one | 1194424-83-3

• 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: (5S)-5-((1H-tetrazol-5-yl)methyl)-2,2,3-trimethylimidazolidin-4-one
• 英文别名: (5S)-2,2,3-trimethyl-5-(2H-tetrazol-5-ylmethyl)imidazolidin-4-one
• CAS: 1194424-83-3
• 化学式: C₈H₁₄N₆O
• 分子量: 210.239
• InChiKey: UVQXQKCOPBLLOY-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[(4S)-1,2,2-trimethyl-5-oxoimidazolidin-4-yl]acetonitrile 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (5S)-5-((1H-tetrazol-5-yl)methyl)-2,2,3-trimethylimidazolidin-4-one
  参考文献：
  名称：

  Synthesis and application of novel imidazole and 1H-tetrazolic acid containing catalysts in enantioselective organocatalyzed Diels–Alder reactions

  摘要：

  Herein we report studies on the organocatalytic Diels-Alder reaction using a variety of catalysts capable of activating alpha,beta-unsaturated carbonyl compounds for reactions with dienes. The structurally attractive catalysts 4 and 14 were utilized in the enantioselective organocatalytic Diels-Alder reactions. Catalyst 4 provided the products in fair yields and more importantly in good enantioselectivities of up to 83% ee. Catalyst 14 was synthesized in high yield and was assessed in the enantioselective organocatalytic Diels-Alder reaction. Catalyst 14 proved to be a highly active and selective catalyst providing the products in high yield and high enantioselectivities up to 95% ee. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.029

文献信息

• Synthesis and application of novel imidazole and 1H-tetrazolic acid containing catalysts in enantioselective organocatalyzed Diels–Alder reactions
  作者：Antti Hartikka、Leila Hojabri、Partha Pratim Bose、Per I. Arvidsson

  DOI：10.1016/j.tetasy.2009.07.029

  日期：2009.8

  Herein we report studies on the organocatalytic Diels-Alder reaction using a variety of catalysts capable of activating alpha,beta-unsaturated carbonyl compounds for reactions with dienes. The structurally attractive catalysts 4 and 14 were utilized in the enantioselective organocatalytic Diels-Alder reactions. Catalyst 4 provided the products in fair yields and more importantly in good enantioselectivities of up to 83% ee. Catalyst 14 was synthesized in high yield and was assessed in the enantioselective organocatalytic Diels-Alder reaction. Catalyst 14 proved to be a highly active and selective catalyst providing the products in high yield and high enantioselectivities up to 95% ee. (C) 2009 Elsevier Ltd. All rights reserved.