N-(4-pentenyl)glycine methyl ester | 151239-71-3

• 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-(4-pentenyl)glycine methyl ester
• 英文别名: methyl N-pent-4-en-1-ylglycinate；methyl N-(pent-4-enyl)glycinate；Methyl 2-(pent-4-enylamino)acetate
• CAS: 151239-71-3
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: UXXKHFMQOCNOMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  204.8±23.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  N-(4-pentenyl)glycine methyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 59.0h， 生成
  参考文献：
  名称：

  烯丙基羟基膦酸酯：多功能手性构件

  摘要：

  使用一系列钯催化的反应，将烯丙基羟基膦酸酯转化为β和γ取代的氨基膦酸酯。氮亲核试剂和钯催化剂的明智选择可以实现出色的区域和立体化学控制。钯（0）催化的胺加成或甲苯磺酸氨基甲酸酯重排产生γ-取代的膦酸酯，而甲苯磺酸氨基甲酸酯与钯（II）和碱的反应产生恶唑烷酮（β-取代）。

  DOI：

  10.1016/j.jorganchem.2004.11.019
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 5-溴-1-戊烯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 49.0h， 以68.1%的产率得到N-(4-pentenyl)glycine methyl ester
  参考文献：
  名称：

  分子内亲核试剂催化的醛醇内酯化（NCAL）的Aza变体：（3 S，4 R）和（3 R，4 S）4-（羟甲基）吡咯烷丁-3-醇的正式合成

  摘要：

  已经探索了分子内催化，不对称亲核催化剂催化的醛醇内酯化（NCAL）反应的氮杂变体，以通过使用非手性氨基酸来合成β-内酯稠合的氮杂环作为氮杂糖的前体。这些双环β-内酯的用途通过氮杂糖，（3 S，4 R）和（3 R，4 S）4-（羟甲基）吡咯烷丁-3-醇的形式合成来表示。

  DOI：

  10.1016/j.tet.2010.10.085

文献信息

• A Highly Practical RCM Approach towards a Molecular Building Kit of Spirocyclic Reverse Turn Mimics
  作者：Holger Bittermann、Frank Böckler、Jürgen Einsiedel、Peter Gmeiner

  DOI：10.1002/chem.200600432

  日期：2006.8.16

  privileged molecular scaffolds efficiently mimicking reverse turn motifs and thus increasing both binding and selectivity and enabling the elucidation of the bioactive conformation of a natural peptide has attracted remarkable interest. The frequent occurrence of proline in various turn patterns initiated the design of proline-based reverse turn mimetics. As a structural hybridization of a highly potent

  特权分子支架的开发有效地模仿了反向转位基序，从而增加了结合和选择性，并使得能够阐明天然肽的生物活性构象引起了人们的极大兴趣。脯氨酸在各种转弯模式中的频繁出现启动了基于脯氨酸的反向转弯模拟物的设计。作为高效模拟VI型IIβ转角的高效VI型β转角诱导物1与饱和螺环内酰胺3的结构杂交，当Seebach的手性方法的自我复制获得成功时，我们开发了一条通向2型不饱和螺环内酰胺的通用合成路线。与肽偶联反应和Grubbs的闭环复分解反应相结合。通过这种方式，遵循统一的途径，可以获得具有六至九元内酰胺环的各种模型肽。将适当保护的模板引入固相肽合成中会产生天然存在的神经肽神经降压素的不饱和螺环类似物。在高水平的理论上进行的光谱研究和DFT计算表明，反向旋转诱导能力对环尺寸的显着依赖性。尽管不饱和螺环ε-内酰胺12的二级结构与参考γ-内酰胺3a非常吻合，但不饱和δ-内酰胺11却具有超强的β-转角诱导作用，甚至优于3b型β-内酰胺。
• Molecular Building Kit of Fused-Proline-Derived Peptide Mimetics Allowing Specific Adjustment of the Dihedral Ψ Angle
  作者：Juergen Einsiedel、Harald Lanig、Reiner Waibel、Peter Gmeiner

  DOI：10.1021/jo701703e

  日期：2007.11.1

  [Graphics]Proline-derived peptide mimetics have become an area of paramount importance in peptide and protein chemistry. Since protein crystal structures frequently display W angles of 140-170 degrees for prolyl moieties, our intention was to design a completely novel series of 2,3-fused-proline-derived lactams covering this particular conformational space. Extending our recently described toolset of spirocyclic reverse-turn mimetics, we synthesized pyrrolidinyl-fused seven-, eight-, and nine-membered unsaturated lactam model peptides taking advantage of Grubbs' ring-closing metathesis. Investigating the seven-membered lactam 3a by means of IR and NMR spectroscopy and semiempirical molecular dynamics simulations, we could not observe a U-turn conformation; however, increasing the ring size to give eight- and nine-membered congeners revealed moderate and high type II P-turn inducing properties. Interestingly, the conformational properties of our model systems depend on both the ring size of the fused dehydro-Freidinger lactam and the position of the endocyclic double bond. Superior reverse-turn inducing properties could be observed for the fused azacyclononenone 3e. According to diagnostic transanular NOEs, a discrete folding principle of the lactam ring strongly deviating from the regioisomeric lactams 3c,f explains the conformational behavior. Hence, we were able to establish a molecular building kit that allows adjustments of a wide range of naturally occurring proline W angles and thus can be exploited to probe molecular recognition and functional properties of biological systems.
• Application of ring-closing metathesis macrocyclization to the development of Tsg101-binding antagonists
  作者：Fa Liu、Andrew G. Stephen、Abdul A. Waheed、Eric O. Freed、Robert J. Fisher、Terrence R. Burke

  DOI：10.1016/j.bmcl.2009.10.105

  日期：2010.1

  HIV-1 viral budding involves binding of the viral Gag(p6) protein to the ubiquitin E2 variant domain of the human tumor susceptibility gene 101 protein (Tsg101). Recognition of p6 by Tsg101 is mediated in part by a proline-rich motif that contains the sequence 'Pro-Thr-Ala-Pro' ('PTAP'). Using the p6-derived 9-mer sequence 'PEPTAPPEE', we had previously improved peptide binding affinity by employing N-alkylglycine ('peptoid') residues. The current study applies ring-closing metathesis macrocyclization strategies to Tsg101-binding peptide-peptoid hybrids as an approach to stabilize binding conformations and to observe the effects of such macrocyclization on Tsg101-binding affinity and bioavailability. Published by Elsevier Ltd.
• Cross-metathesis of N-alkenyl peptoids with O- or C-allyl glycosides
  作者：Yun-Jin Hu、Rene´ Roy

  DOI：10.1016/s0040-4039(99)00481-5

  日期：1999.4

  Cross-metathesis of several N-alkenyl-containing oligoglycines derivatives (peptoids) with protected O-or C-allyl glycosides of N-acetylglucosamine, galactose, and mannose using Grubbs' ruthenium benzylidene catalyst (Cy3P)(2)Cl2Ru=CHPh (1) has been achieved in 40 to 52% yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• C8-CYCLIC PEPTIDOMIMETICS AS FIBRINOGEN ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0610432A1

  公开（公告）日：1994-08-17