1-(Carbobenzyloxy)-trans-4-(N-methyl-3',4'-dichlorophenylacetamido)-3-pyrrolidinylpiperidine | 133671-21-3

• 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: 1-(Carbobenzyloxy)-trans-4-(N-methyl-3',4'-dichlorophenylacetamido)-3-pyrrolidinylpiperidine
• 英文别名: benzyl (3S,4S)-4-[[2-(3,4-dichlorophenyl)acetyl]-methylamino]-3-pyrrolidin-1-ylpiperidine-1-carboxylate
• CAS: 133671-21-3
• 化学式: C₂₆H₃₁Cl₂N₃O₃
• 分子量: 504.456
• InChiKey: YXTUUQSJGMPEJT-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.09
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  碘代三甲硅烷 、 1-(Carbobenzyloxy)-trans-4-(N-methyl-3',4'-dichlorophenylacetamido)-3-pyrrolidinylpiperidine 以 氯仿 为溶剂， 以68%的产率得到trans-4-(N-Methyl-3',4'-dichlorophenylacetamido)-3-pyrrolidinylpiperidine
  参考文献：
  名称：

  trans-3,4-Diaminopiperidines. Azacyclohexane congeners of .kappa. agonist U-50488

  摘要：

  A variety of trans-3,4-diaminopiperidines were synthesized regio- and stereoselectively from 1-(carbobenzyloxy)-1,2,3,6-tetrahydropyridine. These compounds are structurally related to the selective kappa agonist U-50488. The two key reactions which determine the stereo- and regiochemistry of the final products involve the S(N)2 ring opening of an epoxide and an aziridinium species. Reaction of secondary amines with epoxide 3 led to ca. 1.5:1 mixtures of amino alcohols 4 and 5, while S(N)2 attack by methylamine on aziridinium intermediate 6 occurs diastereoselectively at C-4 to give diamines 7. Depending upon the isolation procedure, trimethylsilyl iodide cleavage of the carbobenzyloxy group in compounds 8 and 9 provides either N-benzyl compounds 12 and 13 or the unsubstituted piperidines 10 and 11.

  DOI：

  10.1021/jo00009a038
• 作为产物：
  描述：

  N-苯甲氧基甲酰基-1,2,5,6-四氢吡啶 在 间氯过氧苯甲酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(Carbobenzyloxy)-trans-4-(N-methyl-3',4'-dichlorophenylacetamido)-3-pyrrolidinylpiperidine
  参考文献：
  名称：

  trans-3,4-Diaminopiperidines. Azacyclohexane congeners of .kappa. agonist U-50488

  摘要：

  A variety of trans-3,4-diaminopiperidines were synthesized regio- and stereoselectively from 1-(carbobenzyloxy)-1,2,3,6-tetrahydropyridine. These compounds are structurally related to the selective kappa agonist U-50488. The two key reactions which determine the stereo- and regiochemistry of the final products involve the S(N)2 ring opening of an epoxide and an aziridinium species. Reaction of secondary amines with epoxide 3 led to ca. 1.5:1 mixtures of amino alcohols 4 and 5, while S(N)2 attack by methylamine on aziridinium intermediate 6 occurs diastereoselectively at C-4 to give diamines 7. Depending upon the isolation procedure, trimethylsilyl iodide cleavage of the carbobenzyloxy group in compounds 8 and 9 provides either N-benzyl compounds 12 and 13 or the unsubstituted piperidines 10 and 11.

  DOI：

  10.1021/jo00009a038

文献信息

• DANDREA, STAN V.;MICHALSON, ERIC T.;FREEMAN, JEREMIAH P.;CHIDESTER, CONNI+, J. ORG. CHEM., 56,(1991) N, C. 3133-3137
  作者：DANDREA, STAN V.、MICHALSON, ERIC T.、FREEMAN, JEREMIAH P.、CHIDESTER, CONNI+

  DOI：——

  日期：——