(+/-)-methyl N-[5-diethylamino-1-(4-methoxyphenyl)pentyl]carbamate | 271577-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-methyl N-[5-diethylamino-1-(4-methoxyphenyl)pentyl]carbamate
• 英文别名: methyl N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]carbamate
• CAS: 271577-49-2
• 化学式: C₁₈H₃₀N₂O₃
• 分子量: 322.448
• InChiKey: WIBHSHJZQIXEBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl N-[5-diethylamino-1-(4-methoxyphenyl)pentyl]carbamate 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以92.4%的产率得到(+/-)-1-amino-5-diethylamino-1-(4-methoxyphenyl)pentane
  参考文献：
  名称：

  Synthesis and antifibrillatory activity of nibentan and its analogues

  摘要：

  A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (+/-)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (+/-)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamid hydrochloride and (+/-)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60-90 min for nibentan). The antifibrillatory activity of (+/-)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00116-1
• 作为产物：
  描述：

  5-(N,N-diethylamino)-1-(4-methoxyphenyl)-1-cyanopentane 在 氢氧化钾 、 双氧水 、 溴 、 sodium methylate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 生成 (+/-)-methyl N-[5-diethylamino-1-(4-methoxyphenyl)pentyl]carbamate
  参考文献：
  名称：

  Synthesis and antifibrillatory activity of nibentan and its analogues

  摘要：

  A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (+/-)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (+/-)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamid hydrochloride and (+/-)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60-90 min for nibentan). The antifibrillatory activity of (+/-)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00116-1

文献信息

• Synthesis and antifibrillatory activity of nibentan and its analogues
  作者：Nadejda K Davydova、Olga S Sizova、Svetlana M Vinogradova、Alexandre I L'vov、Robert G Glushkov、Sergey D Yuzhakov、Michail D Mashkovskiy

  DOI：10.1016/s0223-5234(00)00116-1

  日期：2000.2

  A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (+/-)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (+/-)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamid hydrochloride and (+/-)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60-90 min for nibentan). The antifibrillatory activity of (+/-)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide. (C) 2000 Editions scientifiques et medicales Elsevier SAS.