α-allylglycine amide | 144073-06-3

• 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: α-allylglycine amide
• 英文别名: 2-Amino-4-pentenamide；2-Aminopent-4-enamide；allylglycinamide；DL-allylglycine amide
• CAS: 144073-06-3
• 化学式: C₅H₁₀N₂O
• 分子量: 114.147
• InChiKey: MHCFJYPAEKWGBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-allylglycine amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 2,2'-[(1-prop-2-enylethane-1,2-diyl)bis(nitrilomethylidyne)]diphenol
  参考文献：
  名称：

  Intramolecular alkoxycobaltation: a novel route to the cobalt–carbon bond in a coenzyme B₁₂model

  摘要：

  CoII(salen)衍生物的乙二基带有一条Ï-烯基侧链，与氧气和甲醇或乙醇反应后，通过中间体 CoIII 物种和悬垂烯烃之间的相互作用，产生烷基化产物，在钴和赤道配体之间有一个δ-烷氧基取代的碳桥；CoII(salen)和 1-己烯之间不发生相应的分子间反应。

  DOI：

  10.1039/c39930000832
• 作为产物：
  描述：

  ethyl 2-aminopent-4-enoate 在 氨 作用下， 以 乙醇 为溶剂， 反应 336.0h， 生成 α-allylglycine amide
  参考文献：
  名称：

  Bradbury, Robert H.; Griffiths, David; Rivett, Janet E., Heterocycles, 1990, vol. 31, # 9, p. 1647 - 1653

  摘要：

  DOI：

文献信息

• Bridged (β-alkoxyalkyl)CoIII(salen) complexes by intramolecular alkoxycobaltation of unactivated alkenes: new models for coenzyme B12
  作者：Rolf Blaauw、Irene E. Kingma、Jan H. Laan、Juul L. van der Baan、Sijbe Balt、Martinus W. G. de Bolster、Gerhard W. Klumpp、Wilberth J. J. Smeets、Anthony L. Spek

  DOI：10.1039/b000196l

  日期：——

  but-2-en-1-yl (6c), but-3-en-1-yl (6d)] react with oxygen and alcohols to give organocobalt(III) complexes containing a β-alkoxy-substituted three- or four-carbon bridge between cobalt and the equatorial ligand. NMR and UV–VIS spectroscopic studies show that product formation is a three-stage process involving (1) oxidation of cobalt(II) to produce an (alkoxo)cobalt(III) complex, (2) intramolecular interaction

  Co II（salen）衍生物（Salen = N，N'-亚乙基双[salicylideneaminato]}），其乙二基部分带有一个烯基 侧链R [R = 丙-2-烯-1-基（6a），2-甲基丙-2-烯-1-基（6b），丁-2-烯-1-基（6c），丁-3-烯-1-基（6d）]与氧反应并酒类得到有机钴（III）配合物，在钴和赤道原子之间包含一个β-烷氧基取代的三碳或四碳桥配体。 核磁共振 和UV-VIS光谱研究表明，产品形成是一个三阶段过程，涉及（1） 氧化作用钴（II）生成（烷氧基）钴（III）配合物的过程；（2）钴（III）与烯基 双键产生碳正离子中间体，以及（3） 酒精。在钴（II）配合物6e（R = 3-甲基丁-3-烯-1-基）的情况下，主要产物是桥连的β-亚甲基有机钴（III）配合物10，表明质子 损失与增加竞争 酒类当中间有机钴（III）物种具有较高程度的叔碳正离子化特征时
• [EN] PROCESS FOR THE PREPARATION OF AN alpha-AMINO CARBONYL COMPOUND<br/>[FR] PROCEDE DE PREPARATION D'UN COMPOSE DOLLAR G(A)-AMINO CARBONYLE
  申请人：DSM IP ASSETS BV

  公开号：WO2004078702A1

  公开（公告）日：2004-09-16

  The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.

  该发明涉及一种通过在碱存在下，将亚胺起始物与适当的亲电试剂反应制备α-氨基羰基化合物的方法。这种方法的优点在于，亚胺起始物可以由乙酰乙酸酯或乙酰乙酸酯衍生物和α-氢含量的一级胺反应制备，这些原料通常便宜且易得。这些亚胺起始物通常可以高产率地制备，或几乎不形成任何副产物。
• Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids
  作者：Quirinus B. Broxterman、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1021/jo00049a041

  日期：1992.11

  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.
• Synthesis of racemic .alpha.-amino carboxamides via Lewis acid-mediated reactions of .alpha.-methoxyglycinamide derivatives with allylsilanes: enzymic resolution to optically active .alpha.-amino acids
  作者：Eric C. Roos、Hendrik H. Mooiweer、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Wilhelmus H. J. Boesten、Johan Kamphuis

  DOI：10.1021/jo00051a019

  日期：1992.12

  A short and expedient synthetic route to optically active, saturated and gamma,delta-unsaturated alpha-amino acids is reported. The key step is a BF3.OEt2-mediated reaction of allylsilanes with N-(alkoxycarbonyl)-alpha-methoxyglycinamides 11-15, leading to the corresponding gamma,delta-unsaturated alpha-aminocarboxamides. The genuine S(N)1-character of this process with iminium ion 6 as intermediate is proven in the case of the glycine ester 10. Thus, reaction of enzymatically resolved 10 with pi-nucleophiles leads to racemic products. The most useful iminium precursors are the N-methoxyamides 12-14 providing good yields of coupling products. The most convenient N-protective group is the allyloxycarbonyl group. Deprotection proceeds via a Pd(0)-catalyzed transprotection to the corresponding BOC-protected analogues. Four examples of the enzymatic resolution of alpha-amino carboxamides, by using an L-specific aminopeptidase from Pseudomonas putida, are described in detail. Most notably, secondary N-methoxyamides are good substrates for the enzyme to provide the desired a-amino acids in high optical purity.
• BRADBURY, ROBERT H.;ORIFFITHE, DAVID;RIVETT, JANET E., HETEROCYCLES, 31,(1990) N, C. 1647-1653
  作者：BRADBURY, ROBERT H.、ORIFFITHE, DAVID、RIVETT, JANET E.

  DOI：——

  日期：——