N-benzylidene-DL-alanine amide | 144125-68-8

• 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: N-benzylidene-DL-alanine amide
• 英文别名: N-benzylidenealanine amide；N^α-benzylidene-DL-Ala-NH₂；N-benzylidene-Ala amide；2-(Benzylideneamino)propanamide
• CAS: 144125-68-8
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: SWHJWUPRTFAOTR-UHFFFAOYSA-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)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzylidene-DL-alanine amide 、 3-溴丙烯 生成 C^α-methyl-D,L-allylglycinamide
  参考文献：
  名称：

  Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids

  摘要：

  Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to alpha-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H). Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100%). The solvent used for the reaction is critical. Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems). The scope of the reaction includes alpha-substituted alpha-allylglycine and derivatives as well as beta-substituted beta-allyl-beta-ammo alcohols. In the case of optically active alpha-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H. The products are easily optically enriched by crystallization. Addition of sulfur-based radicals to alpha-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.

  DOI：

  10.1021/jo00049a041

文献信息

• Chemo-enzymatic synthesis of (S)-(+)-cericlamine and related enantiomerically pure 2,2-disubstituted-2-aminoethanols
  作者：Bernard Kaptein、Harold M. Moody、Quirinus B. Broxterman、Johan Kamphuis

  DOI：10.1039/p19940001495

  日期：——

  The synthesis of (S)-(+)-cericlamine (S)-1 and related disubstituted amino alcohols is described as an example of the stereoselective synthesis of amino alcohols from disubstituted amino acids and their corresponding amides. Thus, the amino alcohols (S)-1, (R)-6 and (S)-7 are prepared from enantiomerically pure α-methyl-3,4-dichlorophenylalanine (amide), (R)-4 and (S)-5, respectively, by application

  （S）-（+）-神经酰胺（S）-1和相关的二取代的氨基醇的合成被描述为由二取代的氨基酸及其相应的酰胺立体选择性地合成氨基醇的实例。因此，氨基醇（S）-1，（R）-6和（S）-7由对映体纯的α-甲基-3,4-二氯苯基丙氨酸（酰胺），（R）-4和（S）-制备。5，分别通过应用最近开发的钠-丙烷-1-醇或NaBH 4 -H 2SO 4还原法，然后还原烷基化。（R）-4和（S）-5的制备是通过相转移催化，然后用拟南芥的酰胺酶进行外消旋4的酶促水解。
• Is the Backbone Conformation of C^α-Methyl Proline Restricted to a Single Region?
  作者：Matteo De Poli、Alessandro Moretto、Marco Crisma、Cristina Peggion、Fernando Formaggio、Bernard Kaptein、Quirinus B. Broxterman、Claudio Toniolo

  DOI：10.1002/chem.200900688

  日期：2009.8.10

  the type RCO‐(αMe)Pro‐Xxx‐NHR′ or RCO‐Xxx‐(αMe)Pro‐NHR′, in which Xxx is L (or D)‐Ala, Aib (α‐aminoisoburyric acid), or L (or D)‐(αMe)Pro, long enough to fold into intramolecularly hydrogen‐bonded γ or β turns. The results are compared with those obtained for the corresponding dipeptides based on Pro, a well‐known turn‐forming residue. For the crystal‐state 3D‐structural analysis we used X‐ray diffraction

  C α-甲基-L-脯氨酸或L- (αMe)Pro可能是构象受限最多的α-氨基酸。特别是，它的ω和φ扭转角分别被限制在大约 180 和 -60°，并且理论上只有三个范围的值可用于单肽或更长肽中的ψ，即大约 -30° ( cis′ , 3 10 /α-螺旋结构），60°（反向 γ 转角）或 140°（反式'，聚（L- Pro）n  II 结构）。在这项工作中，我们检查了许多 N αRCO-(αMe)Pro-Xxx-NHR' 或 RCO-Xxx-(αMe)Pro-NHR' 类型的-酰基二肽 N'-烷基酰胺，其中 Xxx 是L (或D )-Ala, Aib (α-氨基异丁酸）或L（或D）-（αMe）Pro，其长度足以折叠成分子内氢键合的 γ 或 β 转角。将结果与基于 Pro（一种众所周知的转角形成残基）的相应二肽获得的结果进行比较。对于晶态 3D 结构分析，我们使用 X 射线衍射，而我们的溶液构象分析主要基于
• 4‐Cyano‐ <i>α</i> ‐methyl‐ <scp>l‐</scp> phenylalanine as a Spectroscopic Marker for the Investigation of PeptaibioticMembrane Interactions
  作者：Marta De Zotti、Sara Bobone、Annalisa Bortolotti、Edoardo Longo、Barbara Biondi、Cristina Peggion、Fernando Formaggio、Claudio Toniolo、Andrea Dalla Bona、Bernard Kaptein、Lorenzo Stella

  DOI：10.1002/cbdv.201400404

  日期：2015.4

  Two analogs of the ten‐amino acid residue, membrane‐active lipopeptaibiotic trichogin GA IV, mono‐labeled with 4‐cyano‐α‐methyl‐L‐phenylalanine, a potentially useful fluorescence and IR absorption probe of the local microenvironment, were synthesized by the solid‐phase methodology and conformationally characterized. The single modification was incorporated either at the N‐terminus (position 1) or near

  由 4-氰基-α-甲基-L-苯丙氨酸单标记的 10 个氨基酸残基的两种类似物，膜活性脂肽生物毛虫 GA IV，一种潜在有用的局部微环境荧光和红外吸收探针，通过以下方法合成固相方法和构象表征。单个修饰被掺入肽主链的 N 端（位置 1）或靠近 C 端（位置 8）。在这两种情况下，被替换的氨基酸都是同样具有螺旋源性的 α-氨基异丁酸 (Aib) 残基。我们通过使用 FT-IR 吸收、CD 和 2D-​​NMR 光谱进行了溶液构象分析。结果表明，两种标记的类似物基本上保持了天然存在的脂肽生物素的整体螺旋倾向。通过荧光和 ATR-IR 吸收技术评估肽膜相互作用。突出了两种肽之间的相似性和差异。总之，我们的数据证实了文献结果，即 4-氰基苄基发色团的一些光谱参数是局部微环境的敏感标志物。