L-N-2-bromobenzyl-N-methyl-Ala-N'-3-(trimethylsilyl)-Gly-OMe | 503034-64-8

• 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: L-N-2-bromobenzyl-N-methyl-Ala-N'-3-(trimethylsilyl)-Gly-OMe
• 英文别名: methyl 2-[[(2S)-2-[(2-bromophenyl)methyl-methylamino]propanoyl]-(3-trimethylsilylprop-2-ynyl)amino]acetate
• CAS: 503034-64-8
• 化学式: C₂₀H₂₉BrN₂O₃Si
• 分子量: 453.451
• InChiKey: JTDAFMOROCAFTE-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-N-2-bromobenzyl-N-methyl-Ala-N'-3-(trimethylsilyl)-Gly-OMe 在 三丁基氯化锡 、 sodium cyanoborohydride 、 1,1'-偶氮(氰基环己烷) 作用下， 以 叔丁醇 为溶剂， 以68%的产率得到(3-methyl-2-oxo-4-trimethylsilanylmethyl-2,5-dihydro-pyrrol-1-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Application of the Radical Cascade of Acyclic Peptide-Based Precursors into Analogues of Type I β-Turn

  摘要：

  含有 N-2-溴苄基、N-甲基取代的丙氨酸或天冬氨酸的二肽、三肽和四肽的自由基环化反应能以良好的收率生成δ,δ-不饱和δ-内酰胺。依靠氢原子转移-消除策略的整体级联反应可作为一种将扁平而坚硬的五元环纳入肽框架的方法。

  DOI：

  10.1055/s-2004-836054
• 作为产物：
  描述：

  methyl (2S)-2-[(2-bromophenyl)methylamino]propanoate 在 N-甲基吗啉 、 盐酸 、 sodium cyanoborohydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 L-N-2-bromobenzyl-N-methyl-Ala-N'-3-(trimethylsilyl)-Gly-OMe
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w

文献信息

• Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams
  作者：Robert Andrukiewicz、Rafał Loska、Vladimir Prisyahnyuk、Krzysztof Staliński

  DOI：10.1021/jo020602w

  日期：2003.2.1

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.
• Application of the Radical Cascade of Acyclic Peptide-Based Precursors into Analogues of Type I β-Turn
  作者：Krzysztof Staliński、Anita Stępień、Rafał Loska、Piotr Cmoch

  DOI：10.1055/s-2004-836054

  日期：——

  Radical cyclizations of di-, tri- and tetrapeptides containing N-2-bromobenzyl,N-methyl-substituted alanine or aspartic acid lead in good yields to α,β-unsaturated γ-lactams. The overall cascade, relying on a hydrogen atom transfer-elimination strategy could serve as a way to incorporate a flat and rigid five-membered ring into the peptide framework.

  含有 N-2-溴苄基、N-甲基取代的丙氨酸或天冬氨酸的二肽、三肽和四肽的自由基环化反应能以良好的收率生成δ,δ-不饱和δ-内酰胺。依靠氢原子转移-消除策略的整体级联反应可作为一种将扁平而坚硬的五元环纳入肽框架的方法。