(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one | 537040-12-3

• 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: (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one
• 英文别名: benzyl (2R,4S)-4-[(E)-3-methoxy-3-oxoprop-1-enyl]-4-methyl-5-oxo-2-phenyl-1,3-oxazolidine-3-carboxylate
• CAS: 537040-12-3
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: UTPFDRGHBYXNFP-SJPVHQJXSA-N

物化性质

• 沸点：
  574.2±50.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one 在 palladium diacetate lithium hydroxide 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.5h， 生成 (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine
  参考文献：
  名称：

  Stereospecific synthesis and absolute configuration of the (2S,3S,4S)-isomer of 2-methyl-2-(carboxycyclopropyl)glycine (MCCG)

  摘要：

  The conformationally restricted metabotropic glutamate receptor antagonist (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine 1 (MCCG) has been synthesized in a stereoselective manner (>99% ee) with the (2S 3S,4S) absolute configuration of this molecule being confirmed by X-ray crystallographic analysis. Subsequent physico-chemical studies were undertaken and the data are at odds with those of the commercially available product. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00049-1
• 作为产物：
  描述：

  methyl (2E)-3-bromoacrylate 、 (2R,4R)-3-苄氧羰基-4-甲基-2-苯基-1,3-恶唑烷-5-酮 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以62%的产率得到(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one
  参考文献：
  名称：

  Stereospecific synthesis and absolute configuration of the (2S,3S,4S)-isomer of 2-methyl-2-(carboxycyclopropyl)glycine (MCCG)

  摘要：

  The conformationally restricted metabotropic glutamate receptor antagonist (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine 1 (MCCG) has been synthesized in a stereoselective manner (>99% ee) with the (2S 3S,4S) absolute configuration of this molecule being confirmed by X-ray crystallographic analysis. Subsequent physico-chemical studies were undertaken and the data are at odds with those of the commercially available product. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00049-1

文献信息

• Stereospecific synthesis and absolute configuration of the (2S,3S,4S)-isomer of 2-methyl-2-(carboxycyclopropyl)glycine (MCCG)
  作者：Hassan Pajouhesh、Kenneth Curry、Hossein Pajouhesh、Mahmonir H. Meresht、Brian Patrick

  DOI：10.1016/s0957-4166(03)00049-1

  日期：2003.3

  The conformationally restricted metabotropic glutamate receptor antagonist (2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine 1 (MCCG) has been synthesized in a stereoselective manner (>99% ee) with the (2S 3S,4S) absolute configuration of this molecule being confirmed by X-ray crystallographic analysis. Subsequent physico-chemical studies were undertaken and the data are at odds with those of the commercially available product. (C) 2003 Elsevier Science Ltd. All rights reserved.