(2S,3S,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-3-phenyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one | 235094-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3S,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-3-phenyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one
• 英文别名: (1R,3S,4S,5S,9S,12R)-5,8,8,12-tetramethyl-4-phenyl-2-oxa-7-azatricyclo[7.4.0.03,7]tridecan-6-one
• CAS: 235094-27-6
• 化学式: C₂₁H₂₉NO₂
• 分子量: 327.467
• InChiKey: AMMBGFXMVFQJRX-VEBAAHATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-3-phenyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以95%的产率得到(3'S,4'S)-8-(3'-methyl-4'-phenylpyrrolidinyl)-menthol
  参考文献：
  名称：

  A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (−)-8-Aminomenthol

  摘要：

  alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.

  DOI：

  10.1021/jo981693t
• 作为产物：
  描述：

  (+/-)-2-phenylselenophenyacetaldehyde 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 10.5h， 生成 (2S,3S,3aS,4aR,6R,8aS)-2,6,9,9-Tetramethyl-3-phenyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one
  参考文献：
  名称：

  A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (−)-8-Aminomenthol

  摘要：

  alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.

  DOI：

  10.1021/jo981693t

文献信息

• A Novel Approach to Chiral, Nonracemic Pyrrolidines by 5-exo-trig Diastereoselective Radical Cyclization on Acrylamides Derived from (−)-8-Aminomenthol
  作者：Celia Andrés、Juan P. Duque-Soladana、Rafael Pedrosa

  DOI：10.1021/jo981693t

  日期：1999.6.1

  alpha,beta-Unsaturated amides supported on perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol as chiral auxiliaries undergo regio- and stereoselective 5-exo-trig radical cyclization leading to diastereomeric five-membered lactams. These cyclization products are transformed into enantiopure 3,4-disubstituted pyrrolidines by reduction with aluminum hydride followed by removal of the menthol appendage.