N,N'-di[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-1,3-benzenedisulfonamide

• 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: N,N'-di[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-1,3-benzenedisulfonamide
• 英文别名: 1-N,3-N-bis[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]benzene-1,3-disulfonamide
• 化学式: C₂₄H₂₈N₂O₆S₂
• 分子量: 504.628
• InChiKey: RUEPVFSTEMFDLT-MQQADFIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1.3苯二磺酰氯 、 去甲麻黄碱 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到N,N'-di[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-1,3-benzenedisulfonamide
  参考文献：
  名称：

  Synthesis of C2-symmetrical bis(1,2-hydroxy sulfonamide) ligands and application in the enantioselective addition of dialkylzinc to aldehydes

  摘要：

  The preparation of several C-2-symmetric disulfonamides derived from 1,2-amino alcohols and disulfonyl derivatives, as well as their use in the titanium tetraisopropoxide-promoted enantioselective additions of dialkylzinc to aldehydes are described. The enantiomeric ratio is up to 96:4, the best results being obtained for aromatic aldehydes with electron-donating groups in the para-position. There are some differences in the enantioselectivity depending on the relative positioning of the amino alcohol moieties in the chiral ligand, the 1,3-disulfonyl derivative being the best system. In the case of para-substituted benzaldehyde derivatives, a negative relationship between the electron-withdrawing character of the para-substituted group and the enantioselectivity of the addition was seen, whereas the more electronic-donating character the substituent has, the higher the observed enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00378-6

文献信息

• Synthesis of C2-symmetrical bis(1,2-hydroxy sulfonamide) ligands and application in the enantioselective addition of dialkylzinc to aldehydes
  作者：Miguel Yus、Diego J. Ramón、Oscar Prieto

  DOI：10.1016/s0957-4166(02)00378-6

  日期：2002.8

  The preparation of several C-2-symmetric disulfonamides derived from 1,2-amino alcohols and disulfonyl derivatives, as well as their use in the titanium tetraisopropoxide-promoted enantioselective additions of dialkylzinc to aldehydes are described. The enantiomeric ratio is up to 96:4, the best results being obtained for aromatic aldehydes with electron-donating groups in the para-position. There are some differences in the enantioselectivity depending on the relative positioning of the amino alcohol moieties in the chiral ligand, the 1,3-disulfonyl derivative being the best system. In the case of para-substituted benzaldehyde derivatives, a negative relationship between the electron-withdrawing character of the para-substituted group and the enantioselectivity of the addition was seen, whereas the more electronic-donating character the substituent has, the higher the observed enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.