ethyl (E)-2-(hydroxyimino)-4-<2(E)-<(3'-phenyl-2'-propenyl)oxy>phenyl>-3-butenoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (E)-2-(hydroxyimino)-4-<2(E)-<(3'-phenyl-2'-propenyl)oxy>phenyl>-3-butenoate
• 英文别名: ethyl (E)-2-(hydroxyimino)-4-{2(E)-[(3'-phenyl-2'-propenyl)oxy]phenyl}-3-butenoate；ethyl (E,2Z)-2-hydroxyimino-4-[2-[(E)-3-phenylprop-2-enoxy]phenyl]but-3-enoate
• 化学式: C₂₁H₂₁NO₄
• 分子量: 351.402
• InChiKey: CRKVHQRJIYUCOM-OPTQYSODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲烷亚磺酰氯化物 、 ethyl (E)-2-(hydroxyimino)-4-<2(E)-<(3'-phenyl-2'-propenyl)oxy>phenyl>-3-butenoate 生成 2-(ethoxycarbonyl)-4-phenyl-5H-<1>benzopyrano<3,4-c>pyridine
  参考文献：
  名称：

  4.pi. Participation of 1-aza-1,3-butadienes in [4 + 2] cycloaddition reactions: intramolecular Diels-Alder reactions of .alpha.,.beta.-unsaturated N-sulfonylimines

  摘要：

  The 4pi participation of alpha,beta-unsaturated N-sulfonylimines in intramolecular Diels-Alder reactions with unactivated dienophiles is detailed in studies which further extend the scope of the [4 + 2] cycloaddition reactions of this new class of 1-aza-1,3-butadienes. Similar to observations made in the intermolecular [4 + 2] cycloaddition reactions, a strong endo diastereoselectivity (>20:1) was observed to dominate in the cycloaddition reaction of 5b versus 5a and 5c. This endo specific reaction may be attributed to the combination of a pronounced, stabilizing secondary orbital interaction and preferred cycloaddition through an anti-endo transition state in which the lone pair on nitrogen and the C-aryl bond of the dienophile lie trans periplanar to one another benefiting from stabilization analogous to the ground-state anomeric effect.

  DOI：

  10.1021/jo00060a022
• 作为产物：
  描述：

  <2-(ethoxycarbonyl)-2-<(2-tetrahydropyranyloxy)imino>ethyl>triphenylphosphonium bromide 在 Amberlyst H-15 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 108.08h， 生成 ethyl (E)-2-(hydroxyimino)-4-<2(E)-<(3'-phenyl-2'-propenyl)oxy>phenyl>-3-butenoate
  参考文献：
  名称：

  4.pi. Participation of 1-aza-1,3-butadienes in [4 + 2] cycloaddition reactions: intramolecular Diels-Alder reactions of .alpha.,.beta.-unsaturated N-sulfonylimines

  摘要：

  The 4pi participation of alpha,beta-unsaturated N-sulfonylimines in intramolecular Diels-Alder reactions with unactivated dienophiles is detailed in studies which further extend the scope of the [4 + 2] cycloaddition reactions of this new class of 1-aza-1,3-butadienes. Similar to observations made in the intermolecular [4 + 2] cycloaddition reactions, a strong endo diastereoselectivity (>20:1) was observed to dominate in the cycloaddition reaction of 5b versus 5a and 5c. This endo specific reaction may be attributed to the combination of a pronounced, stabilizing secondary orbital interaction and preferred cycloaddition through an anti-endo transition state in which the lone pair on nitrogen and the C-aryl bond of the dienophile lie trans periplanar to one another benefiting from stabilization analogous to the ground-state anomeric effect.

  DOI：

  10.1021/jo00060a022

文献信息

• 4.pi. Participation of 1-aza-1,3-butadienes in [4 + 2] cycloaddition reactions: intramolecular Diels-Alder reactions of .alpha.,.beta.-unsaturated N-sulfonylimines
  作者：Dale L. Boger、Wendy L. Corbett

  DOI：10.1021/jo00060a022

  日期：1993.4

  The 4pi participation of alpha,beta-unsaturated N-sulfonylimines in intramolecular Diels-Alder reactions with unactivated dienophiles is detailed in studies which further extend the scope of the [4 + 2] cycloaddition reactions of this new class of 1-aza-1,3-butadienes. Similar to observations made in the intermolecular [4 + 2] cycloaddition reactions, a strong endo diastereoselectivity (>20:1) was observed to dominate in the cycloaddition reaction of 5b versus 5a and 5c. This endo specific reaction may be attributed to the combination of a pronounced, stabilizing secondary orbital interaction and preferred cycloaddition through an anti-endo transition state in which the lone pair on nitrogen and the C-aryl bond of the dienophile lie trans periplanar to one another benefiting from stabilization analogous to the ground-state anomeric effect.