1-aza-5-chloro-10-(hydroxymethyl)-2-oxobicyclo<5.3.0>decane | 133301-31-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: 1-aza-5-chloro-10-(hydroxymethyl)-2-oxobicyclo<5.3.0>decane
• 英文别名: 1-aza-5-chloro-10-hydroxymethyl-2-oxobicyclo<5.3.0>decane；(3S)-8-chloro-3-(hydroxymethyl)-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-5-one
• CAS: 133301-31-2
• 化学式: C₁₀H₁₆ClNO₂
• 分子量: 217.696
• InChiKey: UTOYWQUYGAAEAA-HACHORDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-aza-5-chloro-10-(hydroxymethyl)-2-oxobicyclo<5.3.0>decane 在 氢氧化钾 、 氢气 、 镍 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以73%的产率得到1-aza-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：

  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

文献信息

• Anodic amide oxidations: Fundamental studies concerning the annulation of six- and seven-membered rings onto amines
  作者：Kevin D. Moeller、Scott L. Rothfus、Poh Lee Wong

  DOI：10.1016/s0040-4020(01)87048-4

  日期：1991.1

  electrochemically based annulation procedure for fusing six- and seven-membered rings onto amines has been examined. Both monosubstituted olefins and acetylenes were found to be good nucleophiles for annulating seven-membered rings onto amines. Disubstituted olefins and acetylenes appear to be good nucleophiles for completing the annulation of six-membered rings onto amines. In addition, the compatibility of

  已经研究了烯烃和炔属亲核试剂与用于将六元和七元环融合到胺上的基于电化学的环化程序的相容性。发现单取代的烯烃和乙炔都是将七元环环合到胺上的良好亲核试剂。二取代的烯烃和乙炔似乎是完成六元环在胺上环化的良好亲核试剂。此外，还研究了几种脯氨酸衍生物与环合程序的相容性。