(2S,4aS,7R,8aR)-N-methoxy-3-[(E)-3-phenylbut-2-enyl]-N,4,4,7-tetramethyloctahydro-2H-benzo[e][1,3]oxazine-2-carboxamide | 1200450-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4aS,7R,8aR)-N-methoxy-3-[(E)-3-phenylbut-2-enyl]-N,4,4,7-tetramethyloctahydro-2H-benzo[e][1,3]oxazine-2-carboxamide
• CAS: 1200450-61-8
• 化学式: C₂₄H₃₆N₂O₃
• 分子量: 400.561
• InChiKey: OPNNPDOVTZTIEJ-UHEOZRNISA-N

物化性质

• 沸点：
  495.9±55.0 °C(predicted)
• 密度：
  1.036±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  42.01
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4aS,7R,8aR)-N-methoxy-3-[(E)-3-phenylbut-2-enyl]-N,4,4,7-tetramethyloctahydro-2H-benzo[e][1,3]oxazine-2-carboxamide 、 异丙基氯化镁 以 四氢呋喃 为溶剂， 以1.1 g的产率得到(2S,4aS,7R,8aR)-2-methyl-1-[3-[(E)-3-phenylbut-2-enyl]-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazin-2-yl]propan-1-one
  参考文献：
  名称：

  Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines

  摘要：

  Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.091
• 作为产物：
  描述：

  (2S,4aS,7R,8aR)-2-(ethoxycarbonyl)-3-[(E)-3-phenylbut-2-enyl]-4,4,7-trimethyloctahydro-2H-benzo[e][1,3]oxazine 、 异丙基氯化镁 、 二甲羟胺盐酸盐 以 四氢呋喃 、 乙醚 为溶剂， 以1.6 g的产率得到(2S,4aS,7R,8aR)-N-methoxy-3-[(E)-3-phenylbut-2-enyl]-N,4,4,7-tetramethyloctahydro-2H-benzo[e][1,3]oxazine-2-carboxamide
  参考文献：
  名称：

  Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines

  摘要：

  Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.091