(E)-1-(4-methoxyphenyl)-4-morpholin-4-ylbut-2-ene-1,4-dione | 112162-77-3

• 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: (E)-1-(4-methoxyphenyl)-4-morpholin-4-ylbut-2-ene-1,4-dione
• CAS: 112162-77-3
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: SEBJYUGPJPQXCP-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硼酸 、 (E)-1-(4-methoxyphenyl)-4-morpholin-4-ylbut-2-ene-1,4-dione 在 [(S,S,R,R)-Duanphos)Rh(nbd)]BF₄ 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以96%的产率得到(R)-2,4-bis(4-methoxyphenyl)-1-morpholin-4-ylbutane-1,4-dione
  参考文献：
  名称：

  Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides

  摘要：

  [GRAPHICS]A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to > 99:1, > 96% ee) and moderate to excellent yields (54-99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines, such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets by selective derivatization of either the amide or ketone functional group. A stereochemical model predicting the absolute sense of induction was developed based on single-crystal X-ray structures of product and precatalyst.

  DOI：

  10.1021/jo701682c
• 作为产物：
  描述：

  吗啉 、 (E)-4-(4-methoxyphenyl)-4-oxo-2-butenoic acid 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(E)-1-(4-methoxyphenyl)-4-morpholin-4-ylbut-2-ene-1,4-dione
  参考文献：
  名称：

  Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides

  摘要：

  [GRAPHICS]A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to > 99:1, > 96% ee) and moderate to excellent yields (54-99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines, such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets by selective derivatization of either the amide or ketone functional group. A stereochemical model predicting the absolute sense of induction was developed based on single-crystal X-ray structures of product and precatalyst.

  DOI：

  10.1021/jo701682c

文献信息

• A Novel Aromatic Electrophilic Substitution: Acylation of Aromatics with Cyclic Isoimidium Salts to Yield<i>N,N</i>-Disubstituted β-Aroylcarboxamides
  作者：Alexandru R. Balaban、Theodor-Silviu Balaban、Gerhard V. Boyd

  DOI：10.1055/s-1987-28012

  日期：——

  Cyclic isoimidium perchlorates derived from N,N-diethylphthalamic acid and the monomorpholides of succinic and maleic acid react with benezene, toluene or anisole in the presence of aluminium chloride to give the corresponding ß-aroylcarboxamides in moderate yields.

  来源于N,N-二乙基邻苯二甲酸的环状异吡啶高氯酸盐和琥珀酸及马来酸的单吗啉酯在氯化铝存在下与苯、甲苯或 anisole 反应，产生相应的 β-芳酰羧氨基酯，产率适中。
• Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides
  作者：Jamie L. Zigterman、Jacqueline C. S. Woo、Shawn D. Walker、Jason S. Tedrow、Christopher J. Borths、Emilio E. Bunel、Margaret M. Faul

  DOI：10.1021/jo701682c

  日期：2007.11.1

  [GRAPHICS]A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to > 99:1, > 96% ee) and moderate to excellent yields (54-99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines, such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets by selective derivatization of either the amide or ketone functional group. A stereochemical model predicting the absolute sense of induction was developed based on single-crystal X-ray structures of product and precatalyst.