(4S)-3-[[(4S)-5-oxo-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-3-yl]sulfonyl]-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-5-one | 1104867-78-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S)-3-[[(4S)-5-oxo-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-3-yl]sulfonyl]-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-5-one
• CAS: 1104867-78-8
• 化学式: C₂₂H₂₆B₂N₂O₆S
• 分子量: 468.146
• InChiKey: CGWBGEKMNVZQRE-PMACEKPBSA-N

物化性质

• 沸点：
  529.2±33.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 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：
  102
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  bis-valine N,N'-sulfone 、 二氯苯酚溴酯 在 polymer-bound 2,6-di-tert-butylpyridine 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以98%的产率得到(4S)-3-[[(4S)-5-oxo-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-3-yl]sulfonyl]-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-5-one
  参考文献：
  名称：

  Asymmetric Bisboranes as Bidentate Catalysts for Carbonyl Substrates

  摘要：

  A new class of C-2 symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.

  DOI：

  10.1021/ol802793k
• 作为试剂：
  描述：

  反式肉桂醛 、 环戊二烯 在 (4S)-3-[[(4S)-5-oxo-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-3-yl]sulfonyl]-2-phenyl-4-propan-2-yl-1,3,2-oxazaborolidin-5-one 、 sodium tetrahydroborate 作用下， 以 甲苯 为溶剂， 反应 12.33h， 生成 ((1R,2S,3S,4S)-3-phenylbicyclo[2.2.1]hept-5-en-2-yl)methanol 、 ((1S,2R,3R,4R)-3-phenylbicyclo[2.2.1]hept-5-en-2-yl)methanol
  参考文献：
  名称：

  Asymmetric Bisboranes as Bidentate Catalysts for Carbonyl Substrates

  摘要：

  A new class of C-2 symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.

  DOI：

  10.1021/ol802793k

文献信息

• Asymmetric Bisboranes as Bidentate Catalysts for Carbonyl Substrates
  作者：Andrew A. Rodriguez、Carrie Zhao、Kenneth J. Shea

  DOI：10.1021/ol802793k

  日期：2009.2.5

  A new class of C-2 symmetric bisoxazaborolidinone compounds is described which exhibits bidentate binding to carbonyl substrates. Using the Diels-Alder reaction as a model system, the catalytic activity of these bis-Lewis acids is probed. Reaction rates and selectivities are observed that are higher than the corresponding mono-Lewis acids. This novel system offers a potentially powerful new approach to asymmetric Lewis acid catalysis.