(-)-(1'E)-(2S,7R,9R,10S)-3-benzyl-4,4,7-trimethyl-2-(prop-1'-enyl)octahydro-2H-1,3-benzoxazine | 1206592-13-3

• 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'E)-(2S,7R,9R,10S)-3-benzyl-4,4,7-trimethyl-2-(prop-1'-enyl)octahydro-2H-1,3-benzoxazine
• 英文别名: (2S,4aS,7R,8aR)-3-benzyl-4,4,7-trimethyl-2-[(E)-prop-1-enyl]-4a,5,6,7,8,8a-hexahydro-2H-benzo[e][1,3]oxazine
• CAS: 1206592-13-3
• 化学式: C₂₁H₃₁NO
• 分子量: 313.483
• InChiKey: HPVANVIGTHHXSM-RJIJDGDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硝基乙烷 、 (-)-(1'E)-(2S,7R,9R,10S)-3-benzyl-4,4,7-trimethyl-2-(prop-1'-enyl)octahydro-2H-1,3-benzoxazine 在 异氰酸苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以19.9%的产率得到
  参考文献：
  名称：

  Preparation of 2-alkenylperhydro-1,3-benzoxazines and application for 2-isoxazolines synthesis

  摘要：

  Various 2-substituted-N-benzyl-4,4,7-trimethyl-trans-octahydro-1,3-benzoxazines 2 were prepared from the condensation of (-)-8-benzylaminomenthol 1 derived from (+)-pulegone, with acrolein, crotonaldehyde, cinnamaldehyde, 2(E)-N,N-diisopropyl-4-oxobut-2-enamide, ethyl (2E)-4-oxobut-2-enoate, and 2-furaldehyde in 71-96% yield. The 1,3-dipolar cycloaddition with aceto- and benzonitrile oxide gave the corresponding 2-isoxazoline cycloadducts. The origin of the stereoselectivity (4'S, 5'S-cycloadducts up to 64% de) arises from the cycloaddition of the dipole to the top of the Re,Re-alkene face of dipolarophile 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.033
• 作为产物：
  描述：

  巴豆醛 、 (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 以 甲苯 为溶剂， 反应 15.0h， 以81%的产率得到(-)-(1'E)-(2S,7R,9R,10S)-3-benzyl-4,4,7-trimethyl-2-(prop-1'-enyl)octahydro-2H-1,3-benzoxazine
  参考文献：
  名称：

  Preparation of 2-alkenylperhydro-1,3-benzoxazines and application for 2-isoxazolines synthesis

  摘要：

  Various 2-substituted-N-benzyl-4,4,7-trimethyl-trans-octahydro-1,3-benzoxazines 2 were prepared from the condensation of (-)-8-benzylaminomenthol 1 derived from (+)-pulegone, with acrolein, crotonaldehyde, cinnamaldehyde, 2(E)-N,N-diisopropyl-4-oxobut-2-enamide, ethyl (2E)-4-oxobut-2-enoate, and 2-furaldehyde in 71-96% yield. The 1,3-dipolar cycloaddition with aceto- and benzonitrile oxide gave the corresponding 2-isoxazoline cycloadducts. The origin of the stereoselectivity (4'S, 5'S-cycloadducts up to 64% de) arises from the cycloaddition of the dipole to the top of the Re,Re-alkene face of dipolarophile 2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.033

文献信息

• Preparation of 2-alkenylperhydro-1,3-benzoxazines and application for 2-isoxazolines synthesis
  作者：Carl Poisson、Jean-Éric Lacoste、Fernande D. Rochon、Livain Breau

  DOI：10.1016/j.tetasy.2009.10.033

  日期：2009.11

  Various 2-substituted-N-benzyl-4,4,7-trimethyl-trans-octahydro-1,3-benzoxazines 2 were prepared from the condensation of (-)-8-benzylaminomenthol 1 derived from (+)-pulegone, with acrolein, crotonaldehyde, cinnamaldehyde, 2(E)-N,N-diisopropyl-4-oxobut-2-enamide, ethyl (2E)-4-oxobut-2-enoate, and 2-furaldehyde in 71-96% yield. The 1,3-dipolar cycloaddition with aceto- and benzonitrile oxide gave the corresponding 2-isoxazoline cycloadducts. The origin of the stereoselectivity (4'S, 5'S-cycloadducts up to 64% de) arises from the cycloaddition of the dipole to the top of the Re,Re-alkene face of dipolarophile 2. (C) 2009 Elsevier Ltd. All rights reserved.