(2E)-N,N-diisopropyl-4-oxobut-2-enamide | 1206592-12-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E)-N,N-diisopropyl-4-oxobut-2-enamide
• 英文别名: (E)-4-oxo-N,N-di(propan-2-yl)but-2-enamide
• CAS: 1206592-12-2
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: AGEJRXONBGCDAD-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-N,N-diisopropyl-4-oxobut-2-enamide 、 (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 以 甲苯 为溶剂， 反应 60.0h， 以73%的产率得到(-)-(2E)-3-[(2S,7R,9R,10S)-3-benzyl-4,4,7-trimethyloctahydro-2H-1,3-benzoxazin-2-yl]-N,N-diisopropylprop-2-enamide
  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：

  在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 为溶剂， 以83 mg的产率得到(2E)-N,N-diisopropyl-4-oxobut-2-enamide
  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.