(1R,2S,4S')-(+)-2-(4-isopropyl-2-oxazolin-2-yl)-1-phenyl-1,2-epoxypropane | 432504-76-2

• 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: (1R,2S,4S')-(+)-2-(4-isopropyl-2-oxazolin-2-yl)-1-phenyl-1,2-epoxypropane
• 英文别名: (4S)-2-[(2S,3R)-2-methyl-3-phenyloxiran-2-yl]-4-propan-2-yl-4,5-dihydro-1,3-oxazole
• CAS: 432504-76-2
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: JOTFYLNHOWGOPS-NFAWXSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S')-(+)-2-(4-isopropyl-2-oxazolin-2-yl)-1-phenyl-1,2-epoxypropane 在 palladium on activated charcoal 四甲基乙二胺 、 氢气 、 仲丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 64.5h， 生成 (2S,3S,4S)-4-amino-3,4-diphenyl-2-methyl-2,3-epoxybutyric acid
  参考文献：
  名称：

  Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones

  摘要：

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

  DOI：

  10.1021/ol0618609
• 作为产物：
  描述：

  (4S)-2-chloromethyl-4-isopropyl-2-oxazoline 在 titanium(IV) isopropylate 、 四甲基乙二胺 、 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 生成 (1R,2S,4S')-(+)-2-(4-isopropyl-2-oxazolin-2-yl)-1-phenyl-1,2-epoxypropane
  参考文献：
  名称：

  Stereospecific β-Lithiation of Oxazolinyloxiranes:  Synthesis of α,β-Epoxy-γ-butyrolactones

  摘要：

  Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.

  DOI：

  10.1021/ol025781i

文献信息

• Stereospecific β-Lithiation of Oxazolinyloxiranes:  Synthesis of α,β-Epoxy-γ-butyrolactones
  作者：Vito Capriati、Leonardo Degennaro、Raffaele Favia、Saverio Florio、Renzo Luisi

  DOI：10.1021/ol025781i

  日期：2002.5.1

  Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.
• Stereoselective Synthesis of Novel 4,5-Epoxy-1,2-oxazin-6-ones and α,β-Epoxy-γ-amino Acids from β-Lithiated Oxazolinyloxiranes and Nitrones
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi、Pasqualina Punzi

  DOI：10.1021/ol0618609

  日期：2006.10.1

  A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5] decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-amino gamma- acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.