2-((1R,2S,3R,4S)-6-(tert-butyldimethylsilyloxy)-3-(3-chlorophenyl)-5'-oxo-2'-phenyl-5'Hspiro[bicyclo[2.2.2]oct[5]ene-2,4'-oxazole]-5-yl)acetaldehyde | 1392201-54-5

• 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: 2-((1R,2S,3R,4S)-6-(tert-butyldimethylsilyloxy)-3-(3-chlorophenyl)-5'-oxo-2'-phenyl-5'Hspiro[bicyclo[2.2.2]oct[5]ene-2,4'-oxazole]-5-yl)acetaldehyde
• CAS: 1392201-54-5
• 化学式: C₃₀H₃₄ClNO₄Si
• 分子量: 536.143
• InChiKey: XTKKLQSYWSVQMB-AIUIFLDSSA-N

物化性质

• 沸点：
  580.7±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((1R,2S,3R,4S)-6-(tert-butyldimethylsilyloxy)-3-(3-chlorophenyl)-5'-oxo-2'-phenyl-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77%的产率得到N-((1R,2S,3R,4S)-6-(tert-butyldimethylsilyloxy)-3-(3-chlorophenyl)-5-(2-hydroxyethyl)-2-(hydroxymethyl)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
• 作为产物：
  描述：

  4-(3'-chlorobenzylidene)-2-phenyl-4-oxazolone 、 (E)-2-[2-(tert-butyldimethylsilyloxy)cyclohex-2-enylidene]acetaldehyde 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 苯甲酸 作用下， 以 氘代氯仿 为溶剂， 反应 48.0h， 生成 2-(-6-(tert-butyldimethylsilyloxy)-3-(3-chlorophenyl)-5'-oxo-2'-phenyl-5'Hspiro[bicyclo[2.2.2]oct[5]ene-2,4'-oxazole]-5-yl)acetaldehyde 、 2-((1R,2S,3R,4S)-6-(tert-butyldimethylsilyloxy)-3-(3-chlorophenyl)-5'-oxo-2'-phenyl-5'Hspiro[bicyclo[2.2.2]oct[5]ene-2,4'-oxazole]-5-yl)acetaldehyde
  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