N-((1R,2R,3S,4S)-6-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2-(hydroxymethyl)-3-(thiophen-2-yl)bicyclo[2.2.2]oct-5-en-2-yl)benzamide | 1392201-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((1R,2R,3S,4S)-6-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2-(hydroxymethyl)-3-(thiophen-2-yl)bicyclo[2.2.2]oct-5-en-2-yl)benzamide
• CAS: 1392201-62-5
• 化学式: C₂₈H₃₉NO₄SSi
• 分子量: 513.773
• InChiKey: YEZILWPKZIGSLX-ZXAUVLDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-((1R,2R,3S,4S)-6-(tert-butyldimethylsilyloxy)-5'-oxo-2'-phenyl-3-(thiophen-2-yl)-5'Hspiro[bicyclo[2.2.2]oct[5]ene-2,4'-oxazole]-5-yl)acetaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.17h， 以92%的产率得到N-((1R,2R,3S,4S)-6-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2-(hydroxymethyl)-3-(thiophen-2-yl)bicyclo[2.2.2]oct-5-en-2-yl)benzamide
  参考文献：
  名称：

  Cross-trienamines in Asymmetric Organocatalysis

  摘要：

  Cross-conjugated trienamines are introduced as a new concept in asymmetric organocatalysis. These intermediates are applied in highly enantioselective Diels-Alder and addition reactions, providing functionalized bicyclo[2.2.2]octane compounds and gamma'-addition products, respectively. The nature of the transformations and the intermediates involved are investigated by computational calculations and NMR analysis.

  DOI：

  10.1021/ja3068269