N-tert-butoxycarbonyl-(2S)-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)(pyrrolidin-2-yl)methanol | 939768-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-tert-butoxycarbonyl-(2S)-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)(pyrrolidin-2-yl)methanol
• CAS: 939768-90-8
• 化学式: C₂₆H₂₅F₂₆NO₃
• 分子量: 893.448
• InChiKey: IDTCGDRIDBDQGY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.15
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-(2S)-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)(pyrrolidin-2-yl)methanol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以0.814 g的产率得到(2S)-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)(pyrrolidin-2-yl)methanol
  参考文献：
  名称：

  Novel fluorous prolinol as a pre-catalyst for catalytic asymmetric borane reduction of various ketones

  摘要：

  Novel prolinol carrying two perfluorohexylethyl groups at the g.-position was prepared from L-proline as a starting chiral substrate. Catalytic asymmetric reduction of various ketones, including mono-, di-, and trifluoromethylated acetophenones, using fluorous oxazaborolidines derived from fluorous prolinol afforded the corresponding alcohols in good to excellent yields and with high enantioselectivities (up to 93.2% ee). The fluorous prolinol was recovered without any fluorous solvents or silica gel by simply cooling the organic phase and filtration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.117
• 作为产物：
  描述：

  1-碘-1H,1H,2H,2H-全氟辛烷 、 Boc-L-脯氨酸甲酯 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以57%的产率得到N-tert-butoxycarbonyl-(2S)-bis(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)(pyrrolidin-2-yl)methanol
  参考文献：
  名称：

  Novel fluorous prolinol as a pre-catalyst for catalytic asymmetric borane reduction of various ketones

  摘要：

  Novel prolinol carrying two perfluorohexylethyl groups at the g.-position was prepared from L-proline as a starting chiral substrate. Catalytic asymmetric reduction of various ketones, including mono-, di-, and trifluoromethylated acetophenones, using fluorous oxazaborolidines derived from fluorous prolinol afforded the corresponding alcohols in good to excellent yields and with high enantioselectivities (up to 93.2% ee). The fluorous prolinol was recovered without any fluorous solvents or silica gel by simply cooling the organic phase and filtration. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.117