(4S)-N-ethyl-N-heptyl-4-hydroxy-4-[4-(methanesulfonamido)phenyl]butanamide | 176486-05-8

• 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: (4S)-N-ethyl-N-heptyl-4-hydroxy-4-[4-(methanesulfonamido)phenyl]butanamide
• CAS: 176486-05-8
• 化学式: C₂₀H₃₄N₂O₄S
• 分子量: 398.567
• InChiKey: AJYZQCZASWLBGI-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-N-ethyl-N-heptyl-4-hydroxy-4-[4-(methanesulfonamido)phenyl]butanamide 在 N-甲基吡咯烷酮 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of (R)-N-[4-[4-(dibutylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (artilide fumarate) and the enantiomers of N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (ibutilide fumarate)

  摘要：

  Syntheses of artilide fumarate, its (S) enantiomer and the (R) and (S) enantiomers of ibutilide fumarate were achieved by reduction of the prochiral ketones with (+) and (-)-B-chlorodiisopinocampheylborane. Several methods for analyzing the optical purity of these compounds are presented. The absolute configurations were established by a single crystal X-ray crystallographic analysis of (S)-N-[4-[4-(dibutylamino)-1-hydroxy-4-oxobutyl]phenyl]methanesulfonamide. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00063-8
• 作为产物：
  描述：

  N-乙基-N-庚基-4-[(甲磺酰氨基)苯基]-4-氧代丁酰胺 在 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以46.6%的产率得到(4S)-N-ethyl-N-heptyl-4-hydroxy-4-[4-(methanesulfonamido)phenyl]butanamide
  参考文献：
  名称：

  Synthesis of (R)-N-[4-[4-(dibutylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (artilide fumarate) and the enantiomers of N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (ibutilide fumarate)

  摘要：

  Syntheses of artilide fumarate, its (S) enantiomer and the (R) and (S) enantiomers of ibutilide fumarate were achieved by reduction of the prochiral ketones with (+) and (-)-B-chlorodiisopinocampheylborane. Several methods for analyzing the optical purity of these compounds are presented. The absolute configurations were established by a single crystal X-ray crystallographic analysis of (S)-N-[4-[4-(dibutylamino)-1-hydroxy-4-oxobutyl]phenyl]methanesulfonamide. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00063-8

文献信息

• Synthesis of (R)-N-[4-[4-(dibutylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (artilide fumarate) and the enantiomers of N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide, (E)-2-butenedioate (2:1) salt (ibutilide fumarate)
  作者：Sam C. Perricone、Constance G. Chidester、Jackson B. Hester

  DOI：10.1016/0957-4166(96)00063-8

  日期：1996.3

  Syntheses of artilide fumarate, its (S) enantiomer and the (R) and (S) enantiomers of ibutilide fumarate were achieved by reduction of the prochiral ketones with (+) and (-)-B-chlorodiisopinocampheylborane. Several methods for analyzing the optical purity of these compounds are presented. The absolute configurations were established by a single crystal X-ray crystallographic analysis of (S)-N-[4-[4-(dibutylamino)-1-hydroxy-4-oxobutyl]phenyl]methanesulfonamide. (C) 1996 Elsevier Science Ltd