(2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-((R)-1-phenylselanyl-ethyl)-octahydro-benzo[e][1,3]oxazine | 235094-09-4

• 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-((R)-1-phenylselanyl-ethyl)-octahydro-benzo[e][1,3]oxazine
• 英文别名: (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-[(1R)-1-phenylselanylethyl]-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine
• CAS: 235094-09-4
• 化学式: C₁₉H₂₉NOSe
• 分子量: 366.405
• InChiKey: BDFBBUYJLRGEJF-TWPTVVAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 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-((R)-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
• 作为产物：
  描述：

  苯基溴化硒 、 alkaline earth salt of/the/ methylsulfuric acid 在 二异丙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 生成 (2S,4aS,7R,8aR)-4,4,7-Trimethyl-2-((R)-1-phenylselanyl-ethyl)-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.