Boc-(Nall)Gly-(Nall)Phe-OMe | 292849-75-3

• 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: Boc-(Nall)Gly-(Nall)Phe-OMe
• 英文别名: Boc-N(allyl)Gly-N(allyl)Phe-OMe；methyl (2S)-2-[[2-[(2-methylpropan-2-yl)oxycarbonyl-prop-2-enylamino]acetyl]-prop-2-enylamino]-3-phenylpropanoate
• CAS: 292849-75-3
• 化学式: C₂₃H₃₂N₂O₅
• 分子量: 416.517
• InChiKey: LXONVJBHUDQIBO-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-(Nall)Gly-(Nall)Phe-OMe 在 Grubbs catalyst first generation 作用下， 以 1,1,2-三氯乙烷 为溶剂， 反应 16.0h， 以59%的产率得到(Z)-4-((S)-1-Methoxycarbonyl-2-phenyl-ethyl)-3-oxo-3,4,5,8-tetrahydro-2H-[1,4]diazocine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Cyclic Dipeptides by Ring-Closing Metathesis

  摘要：

  Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-to-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or alpha,alpha-dichlorotoluene as an additive.

  DOI：

  10.1002/1099-0690(200006)2000:12<2335::aid-ejoc2335>3.0.co;2-c
• 作为产物：
  描述：

  N-(2-丙烯基)甘氨酸乙酯 在 sodium hydroxide 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.5h， 生成 Boc-(Nall)Gly-(Nall)Phe-OMe
  参考文献：
  名称：

  Synthesis of Cyclic Dipeptides by Ring-Closing Metathesis

  摘要：

  Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-to-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or alpha,alpha-dichlorotoluene as an additive.

  DOI：

  10.1002/1099-0690(200006)2000:12<2335::aid-ejoc2335>3.0.co;2-c

文献信息

• Synthesis of Cyclic Dipeptides by Ring-Closing Metathesis
  作者：John F. Reichwein、Rob M. J. Liskamp

  DOI：10.1002/1099-0690(200006)2000:12<2335::aid-ejoc2335>3.0.co;2-c

  日期：2000.6

  Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-to-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or alpha,alpha-dichlorotoluene as an additive.