N-Benzoyl-(S)-α-(2-propenyl)-α-alanine | 160281-26-5

• 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-Benzoyl-(S)-α-(2-propenyl)-α-alanine
• 英文别名: (S)-2-benzamido-2-methyl-4-pentenoic acid；2-benzamido-2-methylpent-4-enoic acid；(2S)-2-benzamido-2-methylpent-4-enoic acid
• CAS: 160281-26-5
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: GAEJXRMOPDVQGF-ZDUSSCGKSA-N

物化性质

• 沸点：
  465.5±38.0 °C(predicted)
• 密度：
  1.154±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Benzoyl-(S)-α-(2-propenyl)-α-alanine 在 盐酸 作用下， 反应 2.0h， 以61.6%的产率得到(S)-(-)-α-烯丙基丙氨酸
  参考文献：
  名称：

  Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids

  摘要：

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.

  DOI：

  10.1021/jo00094a038
• 作为产物：
  描述：

  (2R,4S)-3-苯甲酰基-2-(叔丁基)-4-甲基-1,3-恶唑烷-5-酮 在 lithium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 27.5h， 生成 N-Benzoyl-(S)-α-(2-propenyl)-α-alanine
  参考文献：
  名称：

  Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids

  摘要：

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.

  DOI：

  10.1021/jo00094a038

文献信息

• Palladium‐Catalyzed Asymmetric Decarboxylative Allylation of Azlactone Enol Carbonates: Fast Access to Enantioenriched α‐Allyl Quaternary Amino Acids
  作者：Massimo Serra、Eric Bernardi、Giorgio Marrubini、Ersilia De Lorenzi、Lino Colombo

  DOI：10.1002/ejoc.201801363

  日期：2019.1.31

  A practical synthetic protocol for the preparation of enantioenriched 4‐allyl oxazol‐5‐ones was developed. The key Pd‐catalyzed decarboxylative allylation allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. The corresponding quaternary amino acids can be recovered in their enantiopure form or in high optical purity after a single recrystallization

  开发了一种实用的合成方案，用于制备对映体富集的4-烯丙基恶唑5-酮。关键的钯催化脱羧烯丙基化使烯丙基化衍生物的收率很高（83-98％），而ee最高可达85％。在单个重结晶步骤后，可以其对映体纯形式或高光学纯度回收相应的季氨基酸。
• Enantioselective Allylations of Azlactones with Unsymmetrical Acyclic Allyl Esters
  作者：Barry M. Trost、Xavier Ariza

  DOI：10.1021/ja992754n

  日期：1999.11.1

  A catalytic asymmetric synthesis of quaternary amino acids has been developed. The method derives from the asymmetric allylic alkylation (AAA) reaction with chiral palladium catalysts derived from π-allylpalladium chloride dimer and the bis-2-diphenylphosphinobenzamide of R,R-1,2-diaminocyclohexane and related ligands. Highly symmetrical allylating agents such as allyl acetate and 2-methallyl acetate

  已经开发了季氨基酸的催化不对称合成。该方法源自与手性钯催化剂的不对称烯丙基烷基化 (AAA) 反应，该催化剂源自 π-烯丙基氯化钯二聚体和 R,R-1,2-二氨基环己烷和相关配体的双-2-二苯基膦基苯甲酰胺。高度对称的烯丙基化剂如乙酸烯丙酯和乙酸2-甲基烯丙酯产生中等至低的ee。另一方面，1-单取代和1,1-二取代的烯丙基体系可提供出色的结果，ee 通常≥90%。最有趣的二分法出现在对吖内酯的面部选择性上，因为它取决于烯丙基化剂和配体。例如，异戊二烯化产生 99% ee，源自于用 R,R-配体攻击 azlactone 的 si 面，但是肉桂基化产生了 90% 的 ee，这些产物来自于用相同的配体对表面进行攻击。提出了一个基于催化剂产生手性袋的模型来解释这些结果。用一个...
• Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of .alpha.-Substituted .alpha.-Amino Acids
  作者：Alexandra Frauer、Michaela Mehlfuehrer、Klaus Thirring、Heinz Berner

  DOI：10.1021/jo00094a038

  日期：1994.7

  The synthesis of the lipopeptide 1, which exhibits both immunological activity (induction of the colony stimulating factor (CSF)) and stability against metabolic degradation, has been described. A detailed investigation of the course of the ene reaction between the dipeptide 21 and butyl glyoxylate enabled us to use this type of pericyclic reaction for the establishment of the essential pentenoic acid side chain in 23. The required amino acid 15 was obtained by enzymatic hydrolysis of the corresponding rac-ester 19. The absolute configuration of 1 was assigned by oxidative cleavage of the double bond in 24 and 25 followed by comparison of the degradation products with authentic samples.