N-benzylmeroquinene aldehyde | 134261-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-benzylmeroquinene aldehyde
• 英文别名: 2-[(3R,4S)-1-benzyl-3-ethenylpiperidin-4-yl]acetaldehyde
• CAS: 134261-60-2
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: ORWGGTMCALJRFR-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzylmeroquinene aldehyde 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 [1-[(3R,4S)-1-benzyl-3-ethenylpiperidin-4-yl]-3-(6-methoxyquinolin-4-yl)propan-2-yl] acetate
  参考文献：
  名称：

  The Cinchona alkaloids: a silicon-directed synthesis of some advanced intermediates

  摘要：

  N-Benzylmeroquinene aldehyde (5b) was prepared in 10 steps and 21% overall yield from benzylamine. The key transformations involved a stereoselective Lewis acid catalyzed Diels-Alder reaction to produce bicyclic amide 18, which in turn underwent a regioselective Baeyer-Villager oxidation to produce lactone 20. Acid-catalyzed ring opening with concomitant Peterson olefination afforded the meroquinene skeleton, which was converted in high yield to meroquinene aldehyde via a reduction/oxidation sequence. Treatment of this aldehyde with anions derived from 4-methylquinoline smoothly generated alcohols 23a,b, which on acetylation yielded the advanced Cinchona alkaloid intermediates 24a,b.

  DOI：

  10.1021/jo00015a036
• 作为产物：
  描述：

  ((3R,4S)-1-Benzyl-2-oxo-3-vinyl-piperidin-4-yl)-acetic acid methyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 N-benzylmeroquinene aldehyde
  参考文献：
  名称：

  The Cinchona alkaloids: a silicon-directed synthesis of some advanced intermediates

  摘要：

  N-Benzylmeroquinene aldehyde (5b) was prepared in 10 steps and 21% overall yield from benzylamine. The key transformations involved a stereoselective Lewis acid catalyzed Diels-Alder reaction to produce bicyclic amide 18, which in turn underwent a regioselective Baeyer-Villager oxidation to produce lactone 20. Acid-catalyzed ring opening with concomitant Peterson olefination afforded the meroquinene skeleton, which was converted in high yield to meroquinene aldehyde via a reduction/oxidation sequence. Treatment of this aldehyde with anions derived from 4-methylquinoline smoothly generated alcohols 23a,b, which on acetylation yielded the advanced Cinchona alkaloid intermediates 24a,b.

  DOI：

  10.1021/jo00015a036

文献信息

• The Cinchona alkaloids: a silicon-directed synthesis of some advanced intermediates
  作者：Stephen R. Wilson、Martin J. Di Grandi

  DOI：10.1021/jo00015a036

  日期：1991.7

  N-Benzylmeroquinene aldehyde (5b) was prepared in 10 steps and 21% overall yield from benzylamine. The key transformations involved a stereoselective Lewis acid catalyzed Diels-Alder reaction to produce bicyclic amide 18, which in turn underwent a regioselective Baeyer-Villager oxidation to produce lactone 20. Acid-catalyzed ring opening with concomitant Peterson olefination afforded the meroquinene skeleton, which was converted in high yield to meroquinene aldehyde via a reduction/oxidation sequence. Treatment of this aldehyde with anions derived from 4-methylquinoline smoothly generated alcohols 23a,b, which on acetylation yielded the advanced Cinchona alkaloid intermediates 24a,b.