(S)-N-{3-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)phenyl]-2-(methanesulfonylamino)propyl}-4-toluenesulfonamide | 1068142-14-2

• 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: (S)-N-{3-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)phenyl]-2-(methanesulfonylamino)propyl}-4-toluenesulfonamide
• 英文别名: N-[(2S)-3-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)phenyl]-2-(methanesulfonamido)propyl]-4-methylbenzenesulfonamide
• CAS: 1068142-14-2
• 化学式: C₂₈H₂₇F₁₇N₂O₅S₂
• 分子量: 858.638
• InChiKey: VTMQTERXVXWUKG-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  L-酪氨醇 在 吡啶 、 盐酸 、 sodium azide 、 palladium 10% on activated carbon 、 水 、 氢气 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 69.0h， 生成 (S)-N-{3-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)phenyl]-2-(methanesulfonylamino)propyl}-4-toluenesulfonamide
  参考文献：
  名称：

  Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols

  摘要：

  Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.024
• 作为试剂：
  描述：

  二碘甲烷 、 (E)-4-(trityloxy)but-2-en-1-ol 在 (S)-N-{3-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecoxy)phenyl]-2-(methanesulfonylamino)propyl}-4-toluenesulfonamide 、 diethylzinc 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 以70%的产率得到
  参考文献：
  名称：

  Chiral recyclable fluorous disulfonamide ligand for catalytic enantioselective cyclopropanation of allylic alcohols

  摘要：

  Allylic alcohols reacted with Et2Zn and CH2I2 in the presence of a catalytic amount of fluorous disulfonamide 3a to afford the corresponding cyclopropylmethanols in 69%-quantitative yields with 49-85% ee. Recovery of the fluorous ligand 3a was readily performed from the reaction mixture by the fluorous solid-phase extraction (FSPE), and the recovered 3a could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.024

文献信息

• Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand
  作者：Tsuyoshi Miura、Keisuke Itoh、Yumi Yasaku、Naka Koyata、Yasuoki Murakami、Nobuyuki Imai

  DOI：10.1016/j.tetlet.2008.07.125

  日期：2008.9

  Cyclopropanation of allylic alcohols with Et(2)Zn and CH(2)I(2) in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.