N-Pent-4-enoyl-(S)-2-<(benzyloxy)methyl>pyrrolidine | 172946-56-4

• 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: N-Pent-4-enoyl-(S)-2-<(benzyloxy)methyl>pyrrolidine
• 英文别名: N-(pentenoyl)-2-<(benzyloxy)methyl>pyrrolidine；1-[(2S)-2-(phenylmethoxymethyl)pyrrolidin-1-yl]pent-4-en-1-one
• CAS: 172946-56-4
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: CIRVSDPWQJDOEU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Pent-4-enoyl-(S)-2-<(benzyloxy)methyl>pyrrolidine 在 四氯化钛 、 四乙基对甲苯磺酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 1-aza-5-chloro-10-(hydroxymethyl)-2-oxobicyclo<5.3.0>decane
  参考文献：
  名称：

  Conformationally Restricted Peptide Mimetics: The Incorporation of 6,5-Bicyclic Lactam Ring Skeletons into Peptides

  摘要：

  This manuscript describes a convenient procedure for the synthesis of peptide fragments containing 6,5-bicyclic lactam-based conformational constraints. The syntheses capitalize on an electrochemical oxidation to functionalize a substituted proline derivative, an N-acyliminium ion-initiated cyclization in order to form a transient seven-membered-ring lactam, and a rearrangement reaction to form the desired six-membered-ring lactam. The bicyclic lactam products were converted into peptide building blocks and the stereochemistry of the building blocks assigned using two-dimensional NMR techniques. Once synthesized, the building blocks were readily incorporated into peptide fragments with the use of standard peptide synthesis techniques. The synthetic route employed was shown to be compatible with both aryl and branched amino acid side chains.

  DOI：

  10.1021/jo00130a015
• 作为产物：
  描述：

  L-脯氨醇 在 四丁基碘化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.41h， 生成 N-Pent-4-enoyl-(S)-2-<(benzyloxy)methyl>pyrrolidine
  参考文献：
  名称：

  The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions

  摘要：

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.

  DOI：

  10.1021/jo00129a036

文献信息

• The Pent-4-enoyl Group: A Novel Amine-Protecting Group That Is Readily Cleaved under Mild Conditions
  作者：Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/jo00129a036

  日期：1995.12

  Primary and secondary amines are readily protected as N-pent-4-enoyl derivatives, the resulting N-pent-4-enamides being usually highly crystalline. Deprotection is rapidly and efficiently effected under mild conditions by treatment with 3 equiv of iodine in aqueous THF solution. Although an oxidizing medium, these deprotection conditions do not affect oxidizable functionalities including p-methoxybenzyl ethers and alkyl sulfides.
• Conformationally Restricted Peptide Mimetics: The Incorporation of 6,5-Bicyclic Lactam Ring Skeletons into Peptides
  作者：Wenhao Li、Cathleen E. Hanau、Andre dAvignon、Kevin D. Moeller

  DOI：10.1021/jo00130a015

  日期：1995.12

  This manuscript describes a convenient procedure for the synthesis of peptide fragments containing 6,5-bicyclic lactam-based conformational constraints. The syntheses capitalize on an electrochemical oxidation to functionalize a substituted proline derivative, an N-acyliminium ion-initiated cyclization in order to form a transient seven-membered-ring lactam, and a rearrangement reaction to form the desired six-membered-ring lactam. The bicyclic lactam products were converted into peptide building blocks and the stereochemistry of the building blocks assigned using two-dimensional NMR techniques. Once synthesized, the building blocks were readily incorporated into peptide fragments with the use of standard peptide synthesis techniques. The synthetic route employed was shown to be compatible with both aryl and branched amino acid side chains.