(3R,4S)-3-benzoyl-4-methylchroman-2-one | 1194476-92-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: (3R,4S)-3-benzoyl-4-methylchroman-2-one
• 英文别名: (3S,4R)-3-benzoyl-4-methyl-3,4-dihydrochromen-2-one
• CAS: 1194476-92-0
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: WBWUVOCHYXEHSL-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基铝 、 3-苯甲酰基香豆素 在 (R,R)-(PhMeCH)2N-P(-2-O-3,5-diMe-C₆H₂-C₆H₂-3',5'-diMe-2'-O-) 、 copper(II) acetate monohydrate 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 (-)-(3R,4S)-3-benzoyl-4-methylchroman-2-one 、 (3R,4S)-3-benzoyl-4-methylchroman-2-one 、
  参考文献：
  名称：

  Asymmetric conjugate additions to 1,1′-diactivated cyclic enones—a comparative study

  摘要：

  A study of copper-phosphoramidite-catalysed ZnR2 and AlR3 additions to 1,1'-dicarbonyl-activated cyclic Michael acceptors has revealed high enantioselectivities for AlR3 (R = Me, Et) 1,4-addition to a range of 3-acylcoumarins (85-98% ee, trans:cis similar to 90:10) using commercial OF readily available ligands. Large substituents at the 6-position, and to some extent at the 5-position, of the coumarin are less well tolerated, nor is truncation of the coumarin motif to a comparable 2-acylcyclohexenone (ee values up to 78%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.006

文献信息

• Asymmetric conjugate additions to 1,1′-diactivated cyclic enones—a comparative study
  作者：Xiaoping Tang、Alexander J. Blake、William Lewis、Simon Woodward

  DOI：10.1016/j.tetasy.2009.07.006

  日期：2009.8

  A study of copper-phosphoramidite-catalysed ZnR2 and AlR3 additions to 1,1'-dicarbonyl-activated cyclic Michael acceptors has revealed high enantioselectivities for AlR3 (R = Me, Et) 1,4-addition to a range of 3-acylcoumarins (85-98% ee, trans:cis similar to 90:10) using commercial OF readily available ligands. Large substituents at the 6-position, and to some extent at the 5-position, of the coumarin are less well tolerated, nor is truncation of the coumarin motif to a comparable 2-acylcyclohexenone (ee values up to 78%). (C) 2009 Elsevier Ltd. All rights reserved.