(RS)-2-amino-2-phenyl-4-pentenoic acid amide | 142421-36-1

• 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: (RS)-2-amino-2-phenyl-4-pentenoic acid amide
• 英文别名: 2-Amino-2-phenylpent-4-enamide
• CAS: 142421-36-1
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: MZOCBJYIKMWEMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (RS)-2-amino-2-phenyl-4-pentenoic acid amide 在 盐酸 作用下， 反应 18.0h， 以42%的产率得到D,L-α-Allyl-PG
  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
• 作为产物：
  描述：

  α-benzylideneamino-α-phenylacetamide 、 3-溴丙烯 在 四丁基硫酸氢铵 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(RS)-2-amino-2-phenyl-4-pentenoic acid amide
  参考文献：
  名称：

  相转移催化烷基化法合成α，α-二取代的α-氨基酸酰胺

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)61112-7

文献信息

• A convenient synthesis of protected (R)-α-phenylproline derivatives using the Mitsunobu reaction
  作者：J. Van Betsbrugge、D. Tourwé、B. Kaptein、H. Kierkels、R. Broxterman

  DOI：10.1016/s0040-4020(97)00521-8

  日期：1997.7

  hydrolysis, the resulting α-allylphenylglycine ethyl ester was enzymatically resolved using PLE. Hydroboration and oxidation of the double bond, Boc-protection and subsequent ring closure using the Mitsunobu reaction protocol gave rise to Boc-(R)-α-phenylproline ethyl ester.

  从外消旋苯基甘氨酸开始以高收率制备Boc-（R）-α-苯基脯氨酸乙酯。苯基甘氨酸的缩合乙酯与苯甲醛布置ñ -亚苄基苯基甘氨酸乙酯，将其相转移催化的条件下烯丙基化。酸性水解后，将所得的α-烯丙基苯基甘氨酸乙酯用PLE酶解。硼氢化和双键的氧化，Boc保护和随后使用Mitsunobu反应方案进行的闭环反应产生了Boc-（R）-α-苯基脯氨酸乙酯。