Propanamide, 2-[(phenylmethylene)amino]- | 138228-58-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Propanamide, 2-[(phenylmethylene)amino]-
• 英文别名: N-benzylidene-D,L-alanineamide；N-benzylidene-D,L-alaninamide
• CAS: 138228-58-7；144125-68-8；145143-06-2
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: SWHJWUPRTFAOTR-KPKJPENVSA-N

物化性质

• 沸点：
  340.4±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.45
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Propanamide, 2-[(phenylmethylene)amino]- 、 肉桂基溴 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-2-Methyl-5-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-pent-4-enoic acid amide
  参考文献：
  名称：

  Enantiopure Cα-tetrasubstituted α-amino acids. Chemo-enzymatic synthesis and application to turn-forming peptides

  摘要：

  By a chemo-enzymatic approach we carried out a large-scale synthesis of four enantiopure, sterically constrained, C-alpha-tetra-substituted alpha -amino acids, all characterized by a sidechain (CCdelta)-C-gamma double bond. By using one of them (L-Mag), we prepared an N-alpha-protected tetrapeptide benzylamide which was shown to adopt a beta -turn conformation and to efficiently undergo ring-closing olefin metathesis. (C) 2001 Elsevier Science Led. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00548-8

文献信息

• Synthesis of α,α-disubstituted α-amino acid amides by phase-transfer catalyzed alkylation
  作者：Bernard Kaptein、Wilhelmus H.J. Boesten、Quirinus B. Broxterman、Hans E. Schoemaker、Johan Kamphuis

  DOI：10.1016/s0040-4039(00)61112-7

  日期：1992.9

  α,α-Disubstituted α-amino acid amides were prepared in 17–86% chemical yield by the phase-transfer catalyzed alkylation of N-benzylidene α-H amino acid amides, followed by weak acidic hydrolysis of the Schiff bases.

  通过相转移催化N-亚苄基α-H氨基酸酰胺的烷基化反应，然后对席夫碱进行弱酸性水解，可以制备出化学产率为17-86％的α，α-二取代的α-氨基酸酰胺。
• Mag: a Cα-Methylated, Side-chain Unsaturated α-Amino Acid. Introduction into Model Peptides and Conformational Preference
  作者：Cristina Peggion、Roberto Flammengo、Eric Mossel、Quirinus B. Broxterman、Bernard Kaptein、Johan Kamphuis、Fernando Formaggio、Marco Crisma、Claudio Toniolo

  DOI：10.1016/s0040-4020(00)00274-x

  日期：2000.5

  Cα-methylated α-amino acid Mag, characterized by a side-chain CγCδ bond. We also prepared a series of model peptides containing Mag in combination with Aib and Ala. All of the peptides were fully characterized and their conformational preference was determined in solution by FT-IR absorption and 1H NMR investigations. X-Ray diffraction analyses of l-Mag, a derivative and three peptides are also presented

  通过化学-酶促的方法，我们合成中的手性，C α甲基化的α氨基酸MAG，其特征在于，一个侧链C γ C δ键。我们还制备了一系列含有MAg以及Aib和Ala的模型肽，并对所有肽进行了充分表征，并通过FT-IR吸收和1 H NMR研究了它们在溶液中的构象偏好。还介绍了l-MAg，一种衍生物和三种肽的X射线衍射分析。我们发现，该C α甲基化的α氨基酸是优良的β转角和3 10螺旋前者。完整旋转3 10后，带有两个MAg残基的肽一个在另一个的顶部-螺旋已经合成并表征。