methyl (RS)-2-amino-2-phthalimidomethylhexanoate | 134915-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (RS)-2-amino-2-phthalimidomethylhexanoate
• CAS: 134915-81-4
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: GNNDYUMBPREUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (RS)-2-amino-2-phthalimidomethylhexanoate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (3S)-3-[[2-[1-amino-2-(1H-indol-3-yl)ethyl]-5-butyl-1,4-dihydroimidazole-5-carbonyl]amino]-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
  参考文献：
  名称：

  Amide bond replacements : incorporation of a 2,5,5-trisubstituted imidazoline into dipeptides and into a CCK-4 derivative.

  摘要：

  Synthetic methodology for the introduction of a 2,5,5-trisubstituted imidazoline ring as an amide replacement into dipeptide derivatives of Phe, Trp, Lys (N-epsilon-CBZ) and Nle is described. This replacement is also incorporated into the Trp-Nle bond of the tetrapeptide CCK-4 derivative Trp-Nle-Asp-Phe-NH2 and the pentagastrin derivative Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/s0040-4039(00)79701-2
• 作为产物：
  描述：

  DL-己氨酸甲基酯盐酸 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (RS)-2-amino-2-phthalimidomethylhexanoate
  参考文献：
  名称：

  Amide bond replacements : incorporation of a 2,5,5-trisubstituted imidazoline into dipeptides and into a CCK-4 derivative.

  摘要：

  Synthetic methodology for the introduction of a 2,5,5-trisubstituted imidazoline ring as an amide replacement into dipeptide derivatives of Phe, Trp, Lys (N-epsilon-CBZ) and Nle is described. This replacement is also incorporated into the Trp-Nle bond of the tetrapeptide CCK-4 derivative Trp-Nle-Asp-Phe-NH2 and the pentagastrin derivative Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/s0040-4039(00)79701-2

文献信息

• Imidazolines as amide bond replacements
  作者：Ian H. Gilbert、David C. Rees、Alan K. Crockett、Raymond C.F. Jones

  DOI：10.1016/0040-4020(95)00273-b

  日期：1995.5

  This work describes the use of a 2,5,5-trisubstituted imidazoline as an amide bond replacement. The replacement is incorporated into dipeptide derivatives of Phe, Trp, Lys and Nle and also into the CCK-4 analogue Trp-Nle-Asp-Phe-NH2 and the pentagastrin analogue Gly-Trp-Nle-Asp-Phe-NH2. The amide bond replacement is synthesised in enantiomerically and diastereomerically pure form.

  这项工作描述了2,5,5-三取代的咪唑啉作为酰胺键替代物的用途。该替代物被掺入到Phe，Trp，Lys和Nle的二肽衍生物中，并且还被掺入CCK-4类似物Trp-Nle-Asp-Phe-NH 2和五肽胃泌素类似物Gly-Trp-Nle-Asp-Phe-NH 2中。酰胺键置换以对映体和非对映体纯的形式合成。