2-[(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2Z)-ylidene]-ethanol | 176979-83-2

• 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: 2-[(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2Z)-ylidene]-ethanol
• 英文别名: (2Z)-2-[(1S,3S,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-bicyclo[2.2.1]hept-5-enylidene]ethanol
• CAS: 176979-83-2
• 化学式: C₁₆H₂₈O₂Si
• 分子量: 280.483
• InChiKey: WWPIESBANKZCRQ-JBACWGDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2Z)-ylidene]-ethanol 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1R,2S,4S)-3-[2-Trityloxy-eth-(Z)-ylidene]-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
  参考文献：
  名称：

  Enantioselective Total Synthesis of cis-Trikentrin B

  摘要：

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

  DOI：

  10.1021/jo951767q
• 作为产物：
  描述：

  [(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2Z)-ylidene]-acetic acid methyl ester 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 以164 mg的产率得到2-[(1S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-bicyclo[2.2.1]hept-5-en-(2Z)-ylidene]-ethanol
  参考文献：
  名称：

  Enantioselective Total Synthesis of cis-Trikentrin B

  摘要：

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

  DOI：

  10.1021/jo951767q