(4S)-5,5-di(2-methoxy-5-methylphenyl)-4-isopropyloxazolidin-2-one | 1130246-56-8

• 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: (4S)-5,5-di(2-methoxy-5-methylphenyl)-4-isopropyloxazolidin-2-one
• 英文别名: (4S)-5,5-bis(2-methoxy-5-methylphenyl)-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1130246-56-8
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: JVSRXNDKANYHID-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-5,5-di(2-methoxy-5-methylphenyl)-4-isopropyloxazolidin-2-one 、 3-[dimethyl(phenyl)silyl]glutaric anhydride 在 正丁基锂 、 柠檬酸 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基丙烯基脲 为溶剂， 反应 4.5h， 生成 (R)-3-(dimethyl(phenyl)silyl)-5-((S)-4-isopropyl-5,5-bis(2-methoxy-5-methylphenyl)-2-oxooxazolidin-3-yl)-5-oxopentanoic acid
  参考文献：
  名称：

  An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones

  摘要：

  The asymmetric desymmetrization of 3-substituted glutaric anhydrides 1 bearing silyl, aryl and alkyl groups with the lithium salt of chiral oxazolidin-2-ones has been studied. The effects of the substituents at the 4- and 5-positions of the oxazolidin-2-ones on the diastereoselectivity of the anhydride opening were studied in detail. A SuperQuat chiral oxazolidin-2-one 2e with 5,5-diaryl substituents showed optimum selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.010
• 作为产物：
  描述：

  (2S)-2-tert-butyloxycarbonylamino-1,1-di(2-methoxy-5-methylphenyl)-3-methyl-1-butanol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(4S)-5,5-di(2-methoxy-5-methylphenyl)-4-isopropyloxazolidin-2-one
  参考文献：
  名称：

  An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones

  摘要：

  The asymmetric desymmetrization of 3-substituted glutaric anhydrides 1 bearing silyl, aryl and alkyl groups with the lithium salt of chiral oxazolidin-2-ones has been studied. The effects of the substituents at the 4- and 5-positions of the oxazolidin-2-ones on the diastereoselectivity of the anhydride opening were studied in detail. A SuperQuat chiral oxazolidin-2-one 2e with 5,5-diaryl substituents showed optimum selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.010

文献信息

• An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one
  作者：Narendra R. Chaubey、Sunil K. Ghosh

  DOI：10.1016/j.tetasy.2012.08.001

  日期：2012.8

  The asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride 9 with lithiated chiral oxazolidin-2-one 8 has been studied. The desymmetrized product was formed with >90% de and converted into known intermediates for both (+)- and (-)-paroxetines. (c) 2012 Elsevier Ltd. All rights reserved.