1-[(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-(phenylselanylmethyl)-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-3-yl]prop-2-en-1-one | 235094-13-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 1-[(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-(phenylselanylmethyl)-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-3-yl]prop-2-en-1-one
• CAS: 235094-13-0
• 化学式: C₂₁H₂₉NO₂Se
• 分子量: 406.427
• InChiKey: KTWUXULKDMTJOD-UIXUWTQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  1-[(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-(phenylselanylmethyl)-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-3-yl]prop-2-en-1-one 在 aluminium hydride 、 氢氧化钾 、 偶氮二异丁腈 、 4 A molecular sieve 、 三正丁基氢锡 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (S)-3-甲基吡咯烷
  参考文献：
  名称：

  Diastereoselective 5-exo-trig radical cyclisation on N-Acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines

  摘要：

  N-Acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02091-6
• 作为产物：
  描述：

  Phenylselenoacetaldehyde 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-[(2S,4aS,7R,8aR)-4,4,7-trimethyl-2-(phenylselanylmethyl)-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazin-3-yl]prop-2-en-1-one
  参考文献：
  名称：

  Diastereoselective 5-exo-trig radical cyclisation on N-Acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines

  摘要：

  N-Acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02091-6

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.
• Diastereoselective 5-exo-trig radical cyclisation on N-Acryloyl-tetrahydro-1,3-oxazines. A novel approach to enantiopure 3-substituted pyrrolidines
  作者：Celia Andrés、J.Pablo Duque-Soladana、Jesús M. Iglesias、Rafael Pedrosa

  DOI：10.1016/s0040-4039(96)02091-6

  日期：1996.12

  N-Acryloyl-2-(phenylselenomethyl)-tetrahydro-1,3-oxazine 1 generates a carbon-centred radical in the presence of tri-n-butyltin hydride and AIBN. This radical underwent diastereoselective 5-exo-trig cyclisation leading to a mixture of five-membered lactams 2a and 2b (d.e. 68%). Chromatographic separation of the diastereomers and elimination of the chiral auxiliary provided enantiopure (R)-3-methylpyrrolidine in good chemical yield. Copyright (C) 1996 Elsevier Science Ltd