(1R,2S,3S,4S)-ethyl 6-(tert-butyldimethylsilyloxy)-5'-chloro-2'-oxo-5-(2-oxoethyl)spiro[bicyclo[2.2.2]oct[5]ene-2,3'-indoline]-3-carboxylate | 1392201-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1R,2S,3S,4S)-ethyl 6-(tert-butyldimethylsilyloxy)-5'-chloro-2'-oxo-5-(2-oxoethyl)spiro[bicyclo[2.2.2]oct[5]ene-2,3'-indoline]-3-carboxylate
• CAS: 1392201-64-7
• 化学式: C₃₁H₄₂ClNO₇Si
• 分子量: 604.215
• InChiKey: WLAPFAQNDRCUOF-QRDCROCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  41.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  99.21
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S)-ethyl 6-(tert-butyldimethylsilyloxy)-5'-chloro-2'-oxo-5-(2-oxoethyl)spiro[bicyclo[2.2.2]oct[5]ene-2,3'-indoline]-3-carboxylate 、 (S)-(+)-对甲基苯亚磺酰胺 在 titanium (IV) ethoxide 作用下， 以 二氯甲烷 为溶剂， 以39%的产率得到(1R,2S,3S,4S)-ethyl 6-(tert-butyldimethylsilyloxy)-6'-chloro-2'-oxo-5-((E)-2-((S)-ptolylsulfinylimino)ethyl)spiro[bicyclo[2.2.2]oct[5]ene-2,3'-indoline]-3-carboxylate
  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：

  二碳酸二叔丁酯 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 4-二甲氨基吡啶 、 邻氟苯甲酸 作用下， 以 氘代氯仿 、 乙腈 为溶剂， 反应 20.0h， 生成 (1R,2S,3S,4S)-ethyl 6-(tert-butyldimethylsilyloxy)-5'-chloro-2'-oxo-5-(2-oxoethyl)spiro[bicyclo[2.2.2]oct[5]ene-2,3'-indoline]-3-carboxylate
  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