(E)-2-[2-(tert-butyldimethylsilyloxy)cyclohex-2-enylidene]acetaldehyde | 1392201-36-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-2-[2-(tert-butyldimethylsilyloxy)cyclohex-2-enylidene]acetaldehyde
• 英文别名: (2E)-2-[2-[tert-butyl(dimethyl)silyl]oxycyclohex-2-en-1-ylidene]acetaldehyde
• CAS: 1392201-36-3
• 化学式: C₁₄H₂₄O₂Si
• 分子量: 252.429
• InChiKey: RCKARYIYFXPKLW-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (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 、 sodium tetrahydroborate 、 苯甲酸 作用下， 以 甲醇 、 氘代氯仿 、 氯仿 为溶剂， 反应 72.17h， 生成 N-((1R,2S,3R,4S)-6-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2-(hydroxymethyl)-3-phenylbicyclo[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

文献信息

• Cross-trienamines in Asymmetric Organocatalysis
  作者：Kim Søholm Halskov、Tore Kiilerich Johansen、Rebecca L. Davis、Marianne Steurer、Frank Jensen、Karl Anker Jørgensen

  DOI：10.1021/ja3068269

  日期：2012.8.8

  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.