3-(benzyloxycarbonyl)-3-(phenylselanyl)piperidin-2-one | 645398-63-6

• 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: 3-(benzyloxycarbonyl)-3-(phenylselanyl)piperidin-2-one
• 英文别名: Benzyl 2-oxo-3-phenylselanylpiperidine-3-carboxylate
• CAS: 645398-63-6
• 化学式: C₁₉H₁₉NO₃Se
• 分子量: 388.325
• InChiKey: XNQYDVXWIMOMQU-UHFFFAOYSA-N

物化性质

• 沸点：
  555.3±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonyl)-3-(phenylselanyl)piperidin-2-one 在 四丁基溴化铵 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.25h， 生成 3-(benzyloxycarbonyl)-1-[(tert-butoxycarbonyl)methyl]-5,6-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  Synthesis of 3-Aminolactams as X-Gly Constrained Pseudodipeptides and Conformational Study of a Trp-Gly Surrogate

  摘要：

  3-Amino-delta-valerolactams trans-11a-c were synthesized through conjugate addition and Curtius rearrangement and converted into Fmoc-{Trp-Gly}, Fmoc-{Ile-Gly}, and Fmoc-{Phe-Gly} pseudo-dipeptides. Conformational analyses of tripeptide analogues Ac-{Trp-Gly}-Leu-NH2 17a and 17b by NMR experiments and molecular modeling calculations showed that diastereomer 17a adopted a gamma-turn/distorted type II beta-turn structure, whereas diastereomer 17b adopted mainly a gamma-turn structure.

  DOI：

  10.1021/jo035151+
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-(benzyloxycarbonyl)-3-(phenylselanyl)piperidin-2-one
  参考文献：
  名称：

  Synthesis of 3-Aminolactams as X-Gly Constrained Pseudodipeptides and Conformational Study of a Trp-Gly Surrogate

  摘要：

  3-Amino-delta-valerolactams trans-11a-c were synthesized through conjugate addition and Curtius rearrangement and converted into Fmoc-{Trp-Gly}, Fmoc-{Ile-Gly}, and Fmoc-{Phe-Gly} pseudo-dipeptides. Conformational analyses of tripeptide analogues Ac-{Trp-Gly}-Leu-NH2 17a and 17b by NMR experiments and molecular modeling calculations showed that diastereomer 17a adopted a gamma-turn/distorted type II beta-turn structure, whereas diastereomer 17b adopted mainly a gamma-turn structure.

  DOI：

  10.1021/jo035151+

文献信息

• Synthesis of 3-Aminolactams as X-Gly Constrained Pseudodipeptides and Conformational Study of a Trp-Gly Surrogate
  作者：Marta Ecija、Anna Diez、Mario Rubiralta、Núria Casamitjana、Marcelo J. Kogan、Ernest Giralt

  DOI：10.1021/jo035151+

  日期：2003.12.1

  3-Amino-delta-valerolactams trans-11a-c were synthesized through conjugate addition and Curtius rearrangement and converted into Fmoc-Trp-Gly}, Fmoc-Ile-Gly}, and Fmoc-Phe-Gly} pseudo-dipeptides. Conformational analyses of tripeptide analogues Ac-Trp-Gly}-Leu-NH2 17a and 17b by NMR experiments and molecular modeling calculations showed that diastereomer 17a adopted a gamma-turn/distorted type II beta-turn structure, whereas diastereomer 17b adopted mainly a gamma-turn structure.