(αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-5-hydroxy-4,5-dimethyl-2-hexen-1-one | 181221-14-7

• 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: (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-5-hydroxy-4,5-dimethyl-2-hexen-1-one
• 英文别名: (E,4S)-5-hydroxy-4,5-dimethyl-1-phenyl-3-[[(1R)-1-phenylethyl]amino]hex-2-en-1-one
• CAS: 181221-14-7
• 化学式: C₂₂H₂₇NO₂
• 分子量: 337.462
• InChiKey: VGLZTQIBCMQCHK-DBZAMHTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-5-hydroxy-4,5-dimethyl-2-hexen-1-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 122.0h， 生成 (Z)-4,5-Dimethyl-1-phenyl-3-((R)-1-phenyl-ethylamino)-hexa-2,4-dien-1-one
  参考文献：
  名称：

  A directed stereoselective aldol reaction: Simple synthesis of enantiopure δ-hydroxy-β-enamino ketones by condensation of homochiral β-enamino ketones with aldehydes and ketones

  摘要：

  A simple synthesis of enantiopure anti-delta-Hydroxy-beta-enamino ketones 3 by condensation of homochiral lithium dianions derived from beta-enamino ketones 1('') with aldehydes and ketones is reported. The mechanism for the directed enantioselective aldol reaction was investigated. The anti delta-hydroxyenaminone 3 is obtained as the major diastereomer through an open transition state. In acidic conditions the delta-hydroxyenaminones 3 are cyclized to 4-imino-2,3-dihydropyranones 4 which are instable and isomerize spontaneously to gamma alkylidenenaminones 5. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00253-4
• 作为产物：
  描述：

  (R)-1-phenyl-3--pent-2-en-1-one 、 丙酮 在 六甲基磷酰三胺 、 甲基锂 作用下， 生成 (αR,4S)-1-phenyl-3-(N-α-methylbenzyl)amino-5-hydroxy-4,5-dimethyl-2-hexen-1-one
  参考文献：
  名称：

  A directed stereoselective aldol reaction: Simple synthesis of enantiopure δ-hydroxy-β-enamino ketones by condensation of homochiral β-enamino ketones with aldehydes and ketones

  摘要：

  A simple synthesis of enantiopure anti-delta-Hydroxy-beta-enamino ketones 3 by condensation of homochiral lithium dianions derived from beta-enamino ketones 1('') with aldehydes and ketones is reported. The mechanism for the directed enantioselective aldol reaction was investigated. The anti delta-hydroxyenaminone 3 is obtained as the major diastereomer through an open transition state. In acidic conditions the delta-hydroxyenaminones 3 are cyclized to 4-imino-2,3-dihydropyranones 4 which are instable and isomerize spontaneously to gamma alkylidenenaminones 5. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00253-4