(R)-2-(4-methoxyphenyl)-1-morpholin-4-yl-4-phenylbutane-1,4-dione | 959511-73-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (R)-2-(4-methoxyphenyl)-1-morpholin-4-yl-4-phenylbutane-1,4-dione
• 英文别名: (2R)-2-(4-methoxyphenyl)-1-morpholin-4-yl-4-phenylbutane-1,4-dione
• CAS: 959511-73-0
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: QZPCTLXTQZHFHY-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• 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：

  (R)-2-(4-methoxyphenyl)-1-morpholin-4-yl-4-phenylbutane-1,4-dione 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以627.5 mg的产率得到(R)-4-hydroxy-2-(4-methoxyphenyl)-1-morpholin-4-yl-4-phenylbutan-1-one
  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：

  (E)-1-phenyl-4-morpholin-4-ylbut-2-ene-1,4-dione 、 4-甲氧基苯硼酸 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-methoxyphenyl)-1-morpholin-4-yl-4-phenylbutane-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

• 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.