2-[3-(2,2-Diethyl-4-oxo-1,3-benzoxazin-3-yl)-3-oxopropyl]isoindole-1,3-dione | 178396-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[3-(2,2-Diethyl-4-oxo-1,3-benzoxazin-3-yl)-3-oxopropyl]isoindole-1,3-dione
• CAS: 178396-66-2
• 化学式: C₂₃H₂₂N₂O₅
• 分子量: 406.438
• InChiKey: IGIGKEOAYBEDBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  594.5±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(2,2-Diethyl-4-oxo-1,3-benzoxazin-3-yl)-3-oxopropyl]isoindole-1,3-dione 在 4-二甲氨基吡啶 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.33h， 生成 [(2S,3R)-4-(2,2-diethyl-4-oxo-1,3-benzoxazin-3-yl)-3-[(1,3-dioxoisoindol-2-yl)methyl]-4-oxobutan-2-yl] dodecanoate
  参考文献：
  名称：

  A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution

  摘要：

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00132-2
• 作为产物：
  描述：

  水杨酰胺 在 对甲苯磺酸 、 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 22.0h， 生成 2-[3-(2,2-Diethyl-4-oxo-1,3-benzoxazin-3-yl)-3-oxopropyl]isoindole-1,3-dione
  参考文献：
  名称：

  A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution

  摘要：

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00132-2

文献信息

• A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution
  作者：Masahiko Seki、Toshiyuki Furutani、Tsutomu Miyake、Takeshi Yamanaka、Hiroshi Ohmizu

  DOI：10.1016/0957-4166(96)00132-2

  日期：1996.5

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd