2-[(2S,3R)-2-(2,2-diethyl-4-oxo-1,3-benzoxazine-3-carbonyl)-3-hydroxybutyl]isoindole-1,3-dione | 178458-81-6

• 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-[(2S,3R)-2-(2,2-diethyl-4-oxo-1,3-benzoxazine-3-carbonyl)-3-hydroxybutyl]isoindole-1,3-dione
• CAS: 178458-81-6
• 化学式: C₂₅H₂₆N₂O₆
• 分子量: 450.491
• InChiKey: XPLIVSMOUYUPKC-BEFAXECRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(2S,3R)-2-(2,2-diethyl-4-oxo-1,3-benzoxazine-3-carbonyl)-3-hydroxybutyl]isoindole-1,3-dione 在 咪唑 、 4-二甲氨基吡啶 、 phosphate buffer 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 2-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(2,2-diethyl-4-oxo-1,3-benzoxazine-3-carbonyl)butyl]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
• 作为产物：
  描述：

  水杨酰胺 在 四氯化钛 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 24.33h， 生成 2-[(2S,3R)-2-(2,2-diethyl-4-oxo-1,3-benzoxazine-3-carbonyl)-3-hydroxybutyl]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