methyl (2R)-4-methyl-2-[2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]prop-1-ynyl]anilino]pentanoate | 227288-21-3

• 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: methyl (2R)-4-methyl-2-[2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]prop-1-ynyl]anilino]pentanoate
• CAS: 227288-21-3
• 化学式: C₂₁H₃₀N₂O₄
• 分子量: 374.48
• InChiKey: ZBMDJLBBTCWIGO-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-4-methyl-2-[2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]prop-1-ynyl]anilino]pentanoate 在 盐酸 、 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 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.33h， 生成 (R)-2-[2-(3-{(R)-2-[2-(3-tert-Butoxycarbonylamino-prop-1-ynyl)-phenylamino]-propionylamino}-prop-1-ynyl)-phenylamino]-4-methyl-pentanoic acid
  参考文献：
  名称：

  Synthesis and structure of a small macrocyclic hexapeptide model for antiparallel β-sheet containing two restrained 2-(3′-aminopropynyl)-aniline reverse-turn mimetics

  摘要：

  A new reverse-turn mimetic containing a 2-(3'-aminopropynyl)-phenyl moiety in place of the natural i + 1 and i + 2 turn residues is described in which the key C-C bond was formed from an N-protected propargylamine and 2-iodoaniline using Heck chemistry. Nucleophilic displacement of triflate from activated (2S)-2-hydroxyalkanoate esters by the anilino N-atom, with inversion at C-2, gave homochiral tripeptide mimetics. Two variants of these were coupled and the product was deprotected and then cyclised to give a stable cyclo-hexapeptide analogue that possessed an anti-parallel beta-sheet structure as determined by NMR spectroscopy. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00534-1
• 作为产物：
  描述：

  L-alpha-羟基异己酸 在 2,6-二甲基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 methyl (2R)-4-methyl-2-[2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]prop-1-ynyl]anilino]pentanoate
  参考文献：
  名称：

  Synthesis and structure of a small macrocyclic hexapeptide model for antiparallel β-sheet containing two restrained 2-(3′-aminopropynyl)-aniline reverse-turn mimetics

  摘要：

  A new reverse-turn mimetic containing a 2-(3'-aminopropynyl)-phenyl moiety in place of the natural i + 1 and i + 2 turn residues is described in which the key C-C bond was formed from an N-protected propargylamine and 2-iodoaniline using Heck chemistry. Nucleophilic displacement of triflate from activated (2S)-2-hydroxyalkanoate esters by the anilino N-atom, with inversion at C-2, gave homochiral tripeptide mimetics. Two variants of these were coupled and the product was deprotected and then cyclised to give a stable cyclo-hexapeptide analogue that possessed an anti-parallel beta-sheet structure as determined by NMR spectroscopy. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00534-1