2-{{1-[1-(2-tert-butoxycarbonylamino-hex-5-enoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl}amino}hex-5-enoic acid methyl ester | 410097-71-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-{{1-[1-(2-tert-butoxycarbonylamino-hex-5-enoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl}amino}hex-5-enoic acid methyl ester
• 英文别名: Boc-Abu(vinyl)-D-Pro-Pro-Abu(vinyl)-OMe；methyl (2S)-2-[[(2S)-1-[(2R)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-5-enoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]hex-5-enoate
• CAS: 410097-71-1
• 化学式: C₂₈H₄₄N₄O₇
• 分子量: 548.68
• InChiKey: UHACIXKPSDNYGY-MYGLTJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-{{1-[1-(2-tert-butoxycarbonylamino-hex-5-enoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl}amino}hex-5-enoic acid methyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (Z)-9-tert-butoxycarbonylamino-2,8,18-trioxo-1,7,17-triaza-tricyclo[17.3.0.0^3,7]docos-12-ene-16-carboxylic acid methyl ester 、 (E)-9-tert-butoxycarbonylamino-2,8,18-trioxo-1,7,17-triaza-tricyclo[17.3.0.0^3,7]docos-12-ene-16-carboxylic acid methyl ester
  参考文献：
  名称：

  Conformationally Stable and Constrained Macrocarbocyclic Pseudopeptide Mimics ofβ-Hairpin Structures

  摘要：

  Subjecting a D-PrO-L-PrO template harboring N- and C-terminal omega-alkenyl amino acids to a ring-closure metathesis reaction afforded the corresponding macrocyclic alkenes. A cis-alkene analogue crystallized with one molecule each of water and chloroform, which were retained even after heating at 100degreesC. By using the reduced macrocyclic product as a template, the metathesis could be repeated twice on newly installed omega-alkenyl amino acids to give three-tiered macrocarbocyclic pseudopeptides as mixtures of conformers. NMR studies revealed the high conformational stability of these motifs.

  DOI：

  10.1002/1521-3765(20020104)8:1<111::aid-chem111>3.0.co;2-s
• 作为产物：
  描述：

  Boc-L-高烯丙基甘氨酸 在 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 81.5h， 生成 2-{{1-[1-(2-tert-butoxycarbonylamino-hex-5-enoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl}amino}hex-5-enoic acid methyl ester
  参考文献：
  名称：

  Conformationally Stable and Constrained Macrocarbocyclic Pseudopeptide Mimics ofβ-Hairpin Structures

  摘要：

  Subjecting a D-PrO-L-PrO template harboring N- and C-terminal omega-alkenyl amino acids to a ring-closure metathesis reaction afforded the corresponding macrocyclic alkenes. A cis-alkene analogue crystallized with one molecule each of water and chloroform, which were retained even after heating at 100degreesC. By using the reduced macrocyclic product as a template, the metathesis could be repeated twice on newly installed omega-alkenyl amino acids to give three-tiered macrocarbocyclic pseudopeptides as mixtures of conformers. NMR studies revealed the high conformational stability of these motifs.

  DOI：

  10.1002/1521-3765(20020104)8:1<111::aid-chem111>3.0.co;2-s