(2S)-2-benzylaminopent-4-enoic acid methyl ester | 471242-95-2

• 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: (2S)-2-benzylaminopent-4-enoic acid methyl ester
• 英文别名: (S)-methyl 2-(N-benzyl)aminopent-4-enoate；(-)-(S)-2-(benzylamino)-3-pentenoate；methyl N-benzyl-L-allylglycinate；methyl (2S)-2-(benzylamino)pent-4-enoate
• CAS: 471242-95-2
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: PDBOLUBNEPQKMU-LBPRGKRZSA-N

物化性质

• 沸点：
  299.8±35.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-benzylaminopent-4-enoic acid methyl ester 在 吡啶 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 (R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)aminopent-4-enamido)but-3-enyl acetate
  参考文献：
  名称：

  An Efficient RCM-Based Synthesis of Orthogonally Protected meso-DAP and FK565

  摘要：

  A condensation-ring-close-ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.

  DOI：

  10.1021/jo0485738
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以1.58 g的产率得到(2S)-2-benzylaminopent-4-enoic acid methyl ester
  参考文献：
  名称：

  An Efficient RCM-Based Synthesis of Orthogonally Protected meso-DAP and FK565

  摘要：

  A condensation-ring-close-ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.

  DOI：

  10.1021/jo0485738

文献信息

• Metal-Free Cyclization of <i>ortho</i> -Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls
  作者：Niels Marien、B. Narendraprasad Reddy、Freija De Vleeschouwer、Steven Goderis、Kristof Van Hecke、Guido Verniest

  DOI：10.1002/anie.201800340

  日期：2018.5.14

  tuted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N‐alkenyl‐tethered 2‐aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum

  1-二溴乙烯基-2-硝基取代的芳烃与仲胺之间的有效无金属级联反应可一步完成多环拟吲哚酚的形成。研究了导致这些稠合环系统的反应机理，并认为其涉及硝基芳基化的氨基胺/酰胺的初始形成。这些中间体通过卡宾中间体向N-链烯基拴链的2-氨基异氰酸酯环状异构化，如QTAIM（分子中原子的量子理论）和ELF（电子定位功能）分析所证明。随后的分子内偶极环加成得到标题化合物。
• (<i>S</i>,<i>S</i>)-(+)-Pseudoephedrine α-Iminoglyoxylamide as a Chiral Glycine Cation Equivalent: A Modular and Flexible Approach to Enantioenriched α-Amino Ketones
  作者：Nerea Ruiz、Jose L. Vicario、Dolores Badía、Luisa Carrillo、Beatriz Alonso

  DOI：10.1021/ol800934r

  日期：2008.6.1

  S)-(+)-pseudoephedrine as a valuable chiral electrophile for the preparation of alpha-amino carbonyl compounds. In this context, the addition of Grignard reagents to the azomethine moiety of this chiral electrophile afforded the expected alpha-amino amide adducts in good yields and diastereoselectivities. Moreover, these adducts have been transformed into enantioenriched alpha-amino ketones by exploiting

  我们已经研究了衍生自（S，S）-（+）-伪麻黄碱的α-亚氨基乙醛酰胺作为制备α-氨基羰基化合物的有价值的手性亲电试剂的能力。在这种情况下，将格氏试剂添加到该手性亲电试剂的偶氮甲碱部分中，以良好的收率和非对映选择性提供了预期的α-氨基酰胺加合物。而且，这些加合物已通过利用伪麻黄碱酰胺与有机锂试剂选择性地与氨基甲酰基单加成的能力而转化为对映体富集的α-氨基酮。
• Lee, Jung Gyu; Choi, Kyung Il; Pae, Ae Nim, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 10, p. 1314 - 1317
  作者：Lee, Jung Gyu、Choi, Kyung Il、Pae, Ae Nim、Koh, Hun Yeong、Kang, Yonghan、Cho, Yong Seo

  DOI：——

  日期：——
• An Efficient RCM-Based Synthesis of Orthogonally Protected <i>m</i><i>eso</i>-DAP and FK565
  作者：Juan R. Del Valle、Murray Goodman

  DOI：10.1021/jo0485738

  日期：2004.12.1

  A condensation-ring-close-ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.