(3S,5S,8R,9S)-3-isopropyl-9-methyl-7,7,8-triphenyl-8,9-epoxy-1,6-dioxa-4-azaspiro[4.4]nonane | 432504-77-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,5S,8R,9S)-3-isopropyl-9-methyl-7,7,8-triphenyl-8,9-epoxy-1,6-dioxa-4-azaspiro[4.4]nonane
• 英文别名: (1'S,2S,4S,5'S)-1'-methyl-4',4',5'-triphenyl-4-propan-2-ylspiro[1,3-oxazolidine-2,2'-3,6-dioxabicyclo[3.1.0]hexane]
• CAS: 432504-77-3
• 化学式: C₂₈H₂₉NO₃
• 分子量: 427.543
• InChiKey: DKVJQBUZQFZPIG-PSXRRJEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S,8R,9S)-3-isopropyl-9-methyl-7,7,8-triphenyl-8,9-epoxy-1,6-dioxa-4-azaspiro[4.4]nonane 在 草酸 作用下， 以95%的产率得到(1S,5R)-(-)-1-methyl-4,4,5-triphenyl-3,6-dioxabicyclo[3.1.0]hexan-2-one
  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
• 作为产物：
  描述：

  (4S,2'S,3'R)-(-)-4-isopropyl-2-(3'-phenyloxiranyl)-4,5-dihydrooxazole 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 生成 (3S,5S,8R,9S)-3-isopropyl-9-methyl-7,7,8-triphenyl-8,9-epoxy-1,6-dioxa-4-azaspiro[4.4]nonane
  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.