N-(1-Oxo-2-propen-1-yl)-L-leucyl-L-phenylalanine methyl ester | 499999-37-0

• 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: N-(1-Oxo-2-propen-1-yl)-L-leucyl-L-phenylalanine methyl ester
• 英文别名: methyl (2S)-2-[[(2S)-4-methyl-2-(prop-2-enoylamino)pentanoyl]amino]-3-phenylpropanoate
• CAS: 499999-37-0
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: GUCGDIGQWYMUBR-HOTGVXAUSA-N

物化性质

• 沸点：
  568.6±50.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-Oxo-2-propen-1-yl)-L-leucyl-L-phenylalanine methyl ester 、 Cbz-phenylalanine 4-pyridylthioester 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到N-(leucine-phenylalanine methyl ester)-5-(S)-benzyloxycarbonylamino-4-oxo-6-phenyl-hexane amide
  参考文献：
  名称：

  SmI₂ Reduced Thioesters as Synthons of Unstable Acyl Radicals:  Direct Synthesis of Potential Protease Inhibitors via Intermolecular Radical Addition

  摘要：

  Aromatic alpha-heterosubstituted thioesters were found to undergo radical 1,4-addition reactions to a series of alpha,beta-unsaturated amides and one ester when subjected to the single electron reducing agent, samarium diiodide, at -78 degrees C. These thioesters derived from alpha-amino acids represent a synthetically useful synthon of unstable acyl radicals. This reaction conveniently provides access to gamma-ketoamides and esters in yields up to 90%, structures that are common in various protease inhibitors derived from peptides. Examples with acryloyl and methacryloyl derivatives of alpha-amino acids and dipeptides lead directly to tri- and tetrapeptide mimetics possessing the gamma-ketoamide functionality. No epimerization was observed with the mild conditions used for these reactions.

  DOI：

  10.1021/ja029662+

文献信息

• 1,4 Addition of unprotected pyrrole onto chiral acrylamides: toward synthesis of new polypeptidic architectures
  作者：Alexander Gratais、Xavier Pannecoucke、Samir Bouzbouz

  DOI：10.1039/c4ob01920b

  日期：——

  functionalized acyclic chiral pyrroloamide compounds were synthesized by a simple and robust process involving the creation of a C-C bond between unprotected pyrroles and acyclic chiral acrylamides using Lewis acids. This alkylation reaction using Michael acceptors has been optimized, allowing us to obtain channel selective access to monoalkylated or dialkylated pyrroles, in good yields. Di- and tripeptide deriving

  通过一种简单而稳健的方法，包括使用路易斯酸在未保护的吡咯和无环手性丙烯酰胺之间建立CC键，合成了多种新型的官能化无环手性吡咯酰胺化合物。使用迈克尔受体的烷基化反应已得到优化，使我们能够以良好的收率选择单烷基化或二烷基化吡咯的通道。二肽和三肽衍生的丙烯酰胺也已经用作反应伙伴。
• SmI₂-Promoted Radical Addition of Nitrones to α,β-Unsaturated Amides and Esters:  Synthesis of γ-Amino Acids via a Nitrogen Equivalent to the Ketyl Radical
  作者：Ditte Riber、Troels Skrydstrup

  DOI：10.1021/ol027386y

  日期：2003.1.1

  [reaction: see text] Alkyl nitrones undergo radical addition reactions to a series of alpha,beta-unsaturated amides and esters when subjected to samarium diiodide via a nitrogen equivalent to a ketyl radical anion. This reaction conveniently provides access to a variety of functionalized gamma-amino acids. The methodology was extended to the asymmetric synthesis of 4-substituted gamma-amino acids,

  [反应：见正文]当烷基氮酮经相当于酮基自由基阴离子的氮与二碘化sa反应时，烷基硝酮会与一系列α，β-不饱和酰胺和酯发生自由基加成反应。该反应方便地提供了获得各种官能化的γ-氨基酸的途径。通过将硝酮自由基加成反应与具有手性助剂的丙烯酸酯/酰胺的反应，该方法扩展到了4-取代的γ-氨基酸的不对称合成。
• SmI₂ Reduced Thioesters as Synthons of Unstable Acyl Radicals:  Direct Synthesis of Potential Protease Inhibitors via Intermolecular Radical Addition
  作者：Peter Blakskjær、Bettina Høj、Ditte Riber、Troels Skrydstrup

  DOI：10.1021/ja029662+

  日期：2003.4.1

  Aromatic alpha-heterosubstituted thioesters were found to undergo radical 1,4-addition reactions to a series of alpha,beta-unsaturated amides and one ester when subjected to the single electron reducing agent, samarium diiodide, at -78 degrees C. These thioesters derived from alpha-amino acids represent a synthetically useful synthon of unstable acyl radicals. This reaction conveniently provides access to gamma-ketoamides and esters in yields up to 90%, structures that are common in various protease inhibitors derived from peptides. Examples with acryloyl and methacryloyl derivatives of alpha-amino acids and dipeptides lead directly to tri- and tetrapeptide mimetics possessing the gamma-ketoamide functionality. No epimerization was observed with the mild conditions used for these reactions.