(2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-(phenyl-phenylselanyl-methyl)-octahydro-benzo[e][1,3]oxazine | 235094-12-9

• 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: (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-(phenyl-phenylselanyl-methyl)-octahydro-benzo[e][1,3]oxazine
• 英文别名: (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[phenyl(phenylselanyl)methyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine
• CAS: 235094-12-9
• 化学式: C₂₄H₃₁NOSe
• 分子量: 428.476
• InChiKey: GDOZHKVLNORGOR-VCHAZVNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-(phenyl-phenylselanyl-methyl)-octahydro-benzo[e][1,3]oxazine 在 氢氧化钾 、 lithium aluminium tetrahydride 、 三氯化铝 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 5.67h， 生成 (3R,4S)-4-methyl-3-phenylpyrrolidine N-benzamide
  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：

  (-)-aminomenthol 、 (+/-)-2-phenylselenophenyacetaldehyde 以 苯 为溶剂， 反应 10.0h， 以95%的产率得到(2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-(phenyl-phenylselanyl-methyl)-octahydro-benzo[e][1,3]oxazine
  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.