(2R,3R,3aS,4aR,6R,8aS)-2,3,6,9,9-Pentamethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one | 235094-19-6

• 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: (2R,3R,3aS,4aR,6R,8aS)-2,3,6,9,9-Pentamethyl-octahydro-benzo[e]pyrrolo[2,1-b][1,3]oxazin-1-one
• 英文别名: (1R,3S,4R,5R,9S,12R)-4,5,8,8,12-pentamethyl-2-oxa-7-azatricyclo[7.4.0.03,7]tridecan-6-one
• CAS: 235094-19-6
• 化学式: C₁₆H₂₇NO₂
• 分子量: 265.396
• InChiKey: QZBBHPBGBVLXKD-RWXDJMAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  (2R,3R,3aS,4aR,6R,8aS)-2,3,6,9,9-Pentamethyl-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96%的产率得到(3'R,4'R)-8-(3',4'-dimethylpyrrolidinyl)-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：

  (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-((S)-1-phenylselanyl-ethyl)-octahydro-benzo[e][1,3]oxazine 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 0.5h， 生成 (2R,3R,3aS,4aR,6R,8aS)-2,3,6,9,9-Pentamethyl-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.