cyclo(N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe) | 223595-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: cyclo(N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe)
• 英文别名: cyclo[N(allyl)bAla(3S-Bn)-bAla(3S-Bn)-N(allyl)bAla(3S-Bn)-bAla(3S-Bn)]；(4S,8S,12S,16S)-4,8,12,16-tetrabenzyl-1,9-bis(prop-2-enyl)-1,5,9,13-tetrazacyclohexadecane-2,6,10,14-tetrone
• CAS: 223595-60-6
• 化学式: C₄₆H₅₂N₄O₄
• 分子量: 724.943
• InChiKey: UMRMGBRAUYLWTN-IWWWZYECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclo(N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe) 在 臭氧 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 1.34h， 以74%的产率得到cyclo(N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe-N-(2-hydroxyethyl)-β³-hPhe-β³-hPhe)
  参考文献：
  名称：

  Pseudoaxially Disubstituted Cyclo-β3-tetrapeptide Scaffolds

  摘要：

  An N,N-disubstituted cyclo-beta(3)-tetrapeptide, identified as a potential molecular scaffold, has been synthesised on a multigram scale from beta-homophenylalanine by employing a nosylate-based protection strategy. C-2-Symmetric derivatives containing pseudoaxial, combinatorially addressable functionalities have been prepared from the parent cyclopeptide. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00666-9
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醇 在 吡啶 、 lithium hydroxide 、 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 PyoBrP 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 N,N-二甲基甲酰胺二甲基缩醛 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 113.0h， 生成 cyclo(N-allyl-β³-hPhe-β³-hPhe-N-allyl-β³-hPhe-β³-hPhe)
  参考文献：
  名称：

  Design and synthesis of a novel cyclo-β-tetrapeptide

  摘要：

  N-Substituted tetralactams (cyclo-beta-tetrapeptides) have been identified as potential molecular scaffolds by computer-aided design; compound 2, arising from L-beta-homophenylalanine, has been prepared as a model system and its structure elucidated by single crystal X-ray analysis and NMR spectroscopy. (C) 1999 Elsevier Science Ltd. AU rights reserved.

  DOI：

  10.1016/s0040-4039(99)00234-8

文献信息

• Pseudoaxially Disubstituted Cyclo-β3-tetrapeptide Scaffolds
  作者：P Sutton

  DOI：10.1016/s0040-4020(00)00666-9

  日期：2000.9.29

  An N,N-disubstituted cyclo-beta(3)-tetrapeptide, identified as a potential molecular scaffold, has been synthesised on a multigram scale from beta-homophenylalanine by employing a nosylate-based protection strategy. C-2-Symmetric derivatives containing pseudoaxial, combinatorially addressable functionalities have been prepared from the parent cyclopeptide. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Design and synthesis of a novel cyclo-β-tetrapeptide
  作者：Peter W. Sutton、Adrian Bradley、Mark R.J. Elsegood、Jaume Farràs、Richard F.W. Jackson、Pedro Romea、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(99)00234-8

  日期：1999.3

  N-Substituted tetralactams (cyclo-beta-tetrapeptides) have been identified as potential molecular scaffolds by computer-aided design; compound 2, arising from L-beta-homophenylalanine, has been prepared as a model system and its structure elucidated by single crystal X-ray analysis and NMR spectroscopy. (C) 1999 Elsevier Science Ltd. AU rights reserved.