(3S)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-hydroxy-4,4-dimethylheptane-1,5-dione | 188177-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3S)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-hydroxy-4,4-dimethylheptane-1,5-dione
• CAS: 188177-16-4
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: GYGRRRVFPIUFEZ-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 (3S)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-hydroxy-4,4-dimethylheptane-1,5-dione 在 4-二甲氨基吡啶 、 pyridin-1-ium 作用下， 反应 72.0h， 以69%的产率得到
  参考文献：
  名称：

  The chromium—Reformatsky reaction: Asymmetric synthesis of the aldol fragment of the cytotoxic epothilons from 3-(2-bromoacyl)-2-oxazolidinones

  摘要：

  In a two step, one pot reaction of 4-benzyl oxazolidinone, 2-bromoacetyl halide, chromium dichloride and a suitable 3-oxo-aldehyde derivative the C1-C6-Me-fragment of epothilons is available in its correct oxidation state and enantiomeric form. Compared to common methods, the chromium-Reformatsky variation preferentially yields the opposite diastereomers and gives improved chemo- and diastereoselection. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02494-x
• 作为产物：
  描述：

  (R)-4-benzyl-2-oxazolidinone lithium salt 在 chromium dichloride 、 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (3S)-1-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-hydroxy-4,4-dimethylheptane-1,5-dione
  参考文献：
  名称：

  The chromium—Reformatsky reaction: Asymmetric synthesis of the aldol fragment of the cytotoxic epothilons from 3-(2-bromoacyl)-2-oxazolidinones

  摘要：

  In a two step, one pot reaction of 4-benzyl oxazolidinone, 2-bromoacetyl halide, chromium dichloride and a suitable 3-oxo-aldehyde derivative the C1-C6-Me-fragment of epothilons is available in its correct oxidation state and enantiomeric form. Compared to common methods, the chromium-Reformatsky variation preferentially yields the opposite diastereomers and gives improved chemo- and diastereoselection. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02494-x

文献信息

• The chromium—Reformatsky reaction: Asymmetric synthesis of the aldol fragment of the cytotoxic epothilons from 3-(2-bromoacyl)-2-oxazolidinones
  作者：Tobias Gabriel、Ludger Wessjohann

  DOI：10.1016/s0040-4039(96)02494-x

  日期：1997.2

  In a two step, one pot reaction of 4-benzyl oxazolidinone, 2-bromoacetyl halide, chromium dichloride and a suitable 3-oxo-aldehyde derivative the C1-C6-Me-fragment of epothilons is available in its correct oxidation state and enantiomeric form. Compared to common methods, the chromium-Reformatsky variation preferentially yields the opposite diastereomers and gives improved chemo- and diastereoselection. (C) 1997 Elsevier Science Ltd.