methyl 2,2-dichloro-2-[(4S,5R)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidin-5-yl]acetate | 147092-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,2-dichloro-2-[(4S,5R)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidin-5-yl]acetate
• CAS: 147092-89-5
• 化学式: C₁₀H₁₅Cl₂NO₄
• 分子量: 284.139
• InChiKey: UGEHZSANRRXCBE-NKWVEPMBSA-N

物化性质

• 沸点：
  422.0±25.0 °C(predicted)
• 密度：
  1.296±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dichloro-2-[(4S,5R)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidin-5-yl]acetate 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 二丁基锡烷 作用下， 生成 (3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate
  参考文献：
  名称：

  Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs

  摘要：

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.

  DOI：

  10.1021/jo00060a006
• 作为产物：
  描述：

  (4S,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxy-1,1-dichloroethyl]-4-methoxy-1,3-oxazolidin-2-one 在 jones reagent 、 三氟化硼乙醚 作用下， 生成 methyl 2,2-dichloro-2-[(4S,5R)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidin-5-yl]acetate
  参考文献：
  名称：

  Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs

  摘要：

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.

  DOI：

  10.1021/jo00060a006

文献信息

• Stereoselective intramolecular radical addition of polyhaloacetyl functions to 2-oxazolones. A facile synthesis of statine and its 2,2,-dichloro and 2,2-difluoro analogs
  作者：Takuya Yamamoto、Seigo Ishibuchi、Tadao Ishizuka、Mamoru Haratake、Takehisa Kunieda

  DOI：10.1021/jo00060a006

  日期：1993.4

  Intramolecular Ru(II)-catalyzed cyclization of 3-[[(1S,2R)-2-[(polyhaloacetoxy)ethoxy]-1-apocam-phanyl]carbonyl]-2-oxazolones results in the exclusive formation of the 12-membered cycloadducts with complete diastereoselectivity, thus providing a new synthetic route to enantiomerically pure statine analogues including dichloro and difluoro derivatives.