(2-Benzyl-2-azaspiro[5.5]undec-4-en-5-yl) trifluoromethanesulfonate | 247089-14-1

• 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: (2-Benzyl-2-azaspiro[5.5]undec-4-en-5-yl) trifluoromethanesulfonate
• 英文别名: (2-benzyl-2-azaspiro[5.5]undec-4-en-5-yl) trifluoromethanesulfonate
• CAS: 247089-14-1
• 化学式: C₁₈H₂₂F₃NO₃S
• 分子量: 389.439
• InChiKey: QCJRJBZVJFDVMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-Benzyl-2-azaspiro[5.5]undec-4-en-5-yl) trifluoromethanesulfonate 在 palladium dihydroxide 盐酸 、 palladium diacetate 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Azaspiro[5.5]undecane-5-carboxylic acid;hydrochloride
  参考文献：
  名称：

  Synthesis and biological evaluation of conformationally restricted gabapentin analogues

  摘要：

  A series of conformationally restricted Gabapentin analogues has been synthesised. The pyrrolidine analogue (R)-2-Aza-spiro[4.5]decane-4-carboxylic acid hydrochloride (3a) had an IC(50) of 120nM, similar to that of Gabapentin (IC(50) = 140nM), at the Gabapentin binding site on the alpha(2)delta subunit of a calcium channel. Compound (3a) also reversed carrageenan induced hyperalgesia in rats, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00383-2
• 作为产物：
  描述：

  N-苄基哌啶酮 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 苯 为溶剂， 生成 (2-Benzyl-2-azaspiro[5.5]undec-4-en-5-yl) trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and biological evaluation of conformationally restricted gabapentin analogues

  摘要：

  A series of conformationally restricted Gabapentin analogues has been synthesised. The pyrrolidine analogue (R)-2-Aza-spiro[4.5]decane-4-carboxylic acid hydrochloride (3a) had an IC(50) of 120nM, similar to that of Gabapentin (IC(50) = 140nM), at the Gabapentin binding site on the alpha(2)delta subunit of a calcium channel. Compound (3a) also reversed carrageenan induced hyperalgesia in rats, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00383-2

文献信息

• Synthesis and biological evaluation of conformationally restricted gabapentin analogues
  作者：Jean-Marie Receveur、Justin S. Bryans、Mark J. Field、Lakhbir Singh、David C. Horwell

  DOI：10.1016/s0960-894x(99)00383-2

  日期：1999.8

  A series of conformationally restricted Gabapentin analogues has been synthesised. The pyrrolidine analogue (R)-2-Aza-spiro[4.5]decane-4-carboxylic acid hydrochloride (3a) had an IC(50) of 120nM, similar to that of Gabapentin (IC(50) = 140nM), at the Gabapentin binding site on the alpha(2)delta subunit of a calcium channel. Compound (3a) also reversed carrageenan induced hyperalgesia in rats, (C) 1999 Elsevier Science Ltd. All rights reserved.