phenyl (2S,4aS,7R,8aR)-[3-[(E)-3-phenylbut-2-enyl]-4,4,7-tri-methyloctahydro-2H-benzo[e][1,3]oxazin-2-yl]ketone | 1200450-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl (2S,4aS,7R,8aR)-[3-[(E)-3-phenylbut-2-enyl]-4,4,7-tri-methyloctahydro-2H-benzo[e][1,3]oxazin-2-yl]ketone
• CAS: 1200450-46-9
• 化学式: C₂₈H₃₅NO₂
• 分子量: 417.591
• InChiKey: CFPPFDRODWGDBV-INSPGVKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  phenyl (2S,4aS,7R,8aR)-[3-[(E)-3-phenylbut-2-enyl]-4,4,7-tri-methyloctahydro-2H-benzo[e][1,3]oxazin-2-yl]ketone 在 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到(1R,2S,4aS,7R,8aR,9aS)-1-phenyl-2-(1-phenylvinyl)-4,4,7-trimethyldecahydro-9-oxa-3a-azacyclopenta[b]naphthalen-1-ol
  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：

  苯基丙醇水合物 、 (1R,2S,5R)-5-methyl-2-[1-[(E)-3-phenylbut-2-enylamino]-1-methylethyl]cyclohexanol 以 甲苯 为溶剂， 反应 38.0h， 以52%的产率得到phenyl (2S,4aS,7R,8aR)-[3-[(E)-3-phenylbut-2-enyl]-4,4,7-tri-methyloctahydro-2H-benzo[e][1,3]oxazin-2-yl]ketone
  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