乙基2-氨基-2-甲基-4-戊烯酸酯 | 114968-87-5

• 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
• 中文名称: 乙基2-氨基-2-甲基-4-戊烯酸酯
• 英文名称: ethyl 2-amino-2-methylpent-4-enoate
• 英文别名: 2-Amino-2-methyl-pent-4-enoic acid ethyl ester
• CAS: 114968-87-5
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: ZLIUKIJCRAXHNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙基2-氨基-2-甲基-4-戊烯酸酯 在 sodium hydroxide 作用下， 反应 20.0h， 生成 (S)-(-)-α-烯丙基丙氨酸 、 (R)-α-(2-Propenyl)-α-alanine ethyl ester 、 (2S,4S)-2-Amino-2,4-dimethylbutyrolactone 、 (2S,4R)-2-Amino-2,4-dimethylbutyrolactone
  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：

  N-tert-butoxycarbonyl-L-alanine ethyl ester 在 4-二甲氨基吡啶 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.5h， 生成 乙基2-氨基-2-甲基-4-戊烯酸酯
  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

• Biphenyl aldehyde-based ternary catalytic system catalyzed Tsuji–Trost allylation of N-unprotected amino acid esters
  作者：Zhao-Wei Wu、Wei Wen、Qi-Xiang Guo

  DOI：10.1016/j.tet.2022.133235

  日期：2023.2

  the direct α-allylation reaction of N-unprotected amino acid esters and allyl alcohol acetates. The chemoselectivity of C-allylation and N-allylation is efficiently controlled and various racemic α,α-disubstituted amino acid esters are generated in good-to-high yields. The target products can be readily converted into structurally diverse α,α-disubstituted amino acids at a gram scale.

  合理设计了一种基于联苯醛的高效三元催化体系，并将其应用于N-未保护氨基酸酯和烯丙醇乙酸酯的直接α-烯丙基化反应。C-烯丙基化和N-烯丙基化的化学选择性得到有效控制，各种外消旋 α,α-二取代氨基酸酯的产率从好到高。目标产物可以很容易地以克级转化为结构多样的 α,α-二取代氨基酸。
• Palladium-catalyzed allylation of α-isocyanocarboxylates
  作者：Yoshihiko Ito、Masaya Sawamura、Masato Matsuoka、Yonetatsu Matsumoto、Tamio Hayashi

  DOI：10.1016/s0040-4039(00)96642-5

  日期：1987.1
• Réactivité d'organozinciques α-insaturés vis à vis de N-(phénylsulfanyl) iminoesters application à la synthèse d' α-aminoacides insaturés, mono- ou disubstitués
  作者：M. Aidene、F. Barbot、L. Miginiac

  DOI：10.1016/s0022-328x(96)06854-4

  日期：1997.4

  A new general synthesis of C-subtituted alpha-aminoacids is described, using at first the regioselective reaction between alpha-unsaturated organozincs and N-(phenylsulfanyl)iminoesters.
• 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.