L-alanine-N-propargylamide | 674778-56-4

• 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-alanine-N-propargylamide
• 英文别名: N-Prop-2-yn-1-yl-L-alaninamide；(2S)-2-amino-N-prop-2-ynylpropanamide
• CAS: 674778-56-4
• 化学式: C₆H₁₀N₂O
• 分子量: 126.158
• InChiKey: HQFIAQYGMQTVSB-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  L-alanine-N-propargylamide 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成
  参考文献：
  名称：

  Synthesis and structure of chiral-at-metal complexes with the ligand (S)-2-[(Sp)-2-(diphenylphosphino)ferrocenyl]-4-isopropyloxazoline

  摘要：

  Half-sandwich complexes of formula [(eta"-ring)MC1L]PF6 [L=(S)-2-[(S-p)-2-(diphenylphosphino)ferrocenyl]-4-isopropyloxazoline; (eta"-ring)M=(eta(5)-C5Me5)Rh; (eta(5)-C5Me5)lr; (eta(6)-p-MeC(6)H(4)iPr)Ru; (eta(6)-p-MeC(6)H(4)iPr)Os] have been prepared and spectroscopically characterised. The molecular structures of the rhodium and iridium compounds have been determined by X-ray crystallography. The related solvate complexes [(eta(5)-C5Me5)ML(Me2CO)](2+) (M=Rh, Ir) are active catalysts for the Diels-Alder reaction between methacrolein and cyclopentadiene. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.09.003
• 作为产物：
  描述：

  ((S)-1-prop-2-ynylcarbamoylethyl)carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以96%的产率得到L-alanine-N-propargylamide
  参考文献：
  名称：

  使用点击化学方法来获取被手性氨基酸取代的单和双位β-环糊精宿主。

  摘要：

  CuI催化的叠氮化物-炔烃环加成反应从单-6-叠氮基-β-环糊精和手性氨基酸开始，已经合成了多种基于手性单和双位环糊精的受体。令人感兴趣的是，微波被证明非常有效地以定量的产率进入广泛的二位β-环糊精受体。

  DOI：

  10.1016/j.carres.2010.11.024

文献信息

• Using click chemistry to access mono- and ditopic β-cyclodextrin hosts substituted by chiral amino acids
  作者：Diem Ngan Tran、Claire Blaszkiewicz、Stéphane Menuel、Alain Roucoux、Karine Philippot、Frédéric Hapiot、Eric Monflier

  DOI：10.1016/j.carres.2010.11.024

  日期：2011.2

  A wide range of chiral mono- and ditopic cyclodextrin-based receptors have been synthesized by CuI-catalyzed azide-alkyne cycloaddition starting from mono-6-azido-beta-cyclodextrin and chiral amino acids. Of interest, microwaves proved very efficient to access a wide range of ditopic beta-cyclodextrin receptors with quantitative yields.

  CuI催化的叠氮化物-炔烃环加成反应从单-6-叠氮基-β-环糊精和手性氨基酸开始，已经合成了多种基于手性单和双位环糊精的受体。令人感兴趣的是，微波被证明非常有效地以定量的产率进入广泛的二位β-环糊精受体。
• Chiral, fluorescent microparticles constructed by optically active helical substituted polyacetylene: preparation and enantioselective recognition ability
  作者：Huajun Huang、Wantai Yang、Jianping Deng

  DOI：10.1039/c4ra16466k

  日期：——

  Microparticles simultaneously showing optical activity and fluorescence were prepared based on fluorescent, optically active helical polymers. Chiral and fluorescent substituted acetylene monomers (L- and D-CFM) were synthesized and then underwent precipitation polymerization in a solvent mixture of CHCl3/n-heptane in the presence of a Rh catalyst at room temperature. The CHCl3/n-heptane mixture at

  基于荧光的光学活性螺旋聚合物制备同时显示光学活性和荧光的微粒。合成手性和荧光取代的乙炔单体（L-和D -CFM），然后在室温下，在Rh催化剂存在下，在CHCl 3 /正庚烷的溶剂混合物中进行沉淀聚合。适当比例的CHCl 3 /正庚烷混合物以高收率提供了直径为910 nm的均匀直径的球形微粒（L-和D- CFMPs）。90重量％）。微粒由聚合物链组成（数均分子量为8700 g mol -1），根据圆二色性和UV-vis吸收光谱法，该聚合物链采用手性螺旋结构。使用荧光显微镜和光谱法测量荧光性质。值得注意的是，新型微粒表现出对丙氨酸和苯乙胺对映体的对映选择性识别能力。但是，L-和D -CFMP在对映选择性识别过程中表现不同。为观察到的对映选择性识别提出了可能的机制。
• Synthesis and structure of chiral-at-metal complexes with the ligand (S)-2-[(Sp)-2-(diphenylphosphino)ferrocenyl]-4-isopropyloxazoline
  作者：Daniel Carmona、Roberto Medrano、Isabel T. Dobrinovich、Fernando J. Lahoz、Joaquina Ferrer、Luis A. Oro

  DOI：10.1016/j.jorganchem.2006.09.003

  日期：2006.12

  Half-sandwich complexes of formula [(eta"-ring)MC1L]PF6 [L=(S)-2-[(S-p)-2-(diphenylphosphino)ferrocenyl]-4-isopropyloxazoline; (eta"-ring)M=(eta(5)-C5Me5)Rh; (eta(5)-C5Me5)lr; (eta(6)-p-MeC(6)H(4)iPr)Ru; (eta(6)-p-MeC(6)H(4)iPr)Os] have been prepared and spectroscopically characterised. The molecular structures of the rhodium and iridium compounds have been determined by X-ray crystallography. The related solvate complexes [(eta(5)-C5Me5)ML(Me2CO)](2+) (M=Rh, Ir) are active catalysts for the Diels-Alder reaction between methacrolein and cyclopentadiene. (c) 2006 Elsevier B.V. All rights reserved.
• Secondary Structure Tuning of a Pseudoprotein Between β‐Meander and α‐Helical Forms in the Solid‐State
  作者：Vignesh Athiyarath、Mithun C. Madhusudhanan、Sooraj Kunnikuruvan、Kana M. Sureshan

  DOI：10.1002/anie.202113129

  日期：2022.1.21

  AbstractTuning the secondary structure of a protein or polymer in the solid‐state is challenging. Here we report the topochemical synthesis of a pseudoprotein and its secondary structure tuning in the solid‐state. We designed the dipeptide monomer N3‐Leu‐Ala‐NH‐CH2‐C≡CH (1) for topochemical azide‐alkyne cycloaddition (TAAC) polymerization. Dipeptide 1 adopts an anti‐parallel β‐sheet‐like stacked arrangement in its crystals. Upon heating, the dipeptide undergoes quantitative TAAC polymerization in a crystal‐to‐crystal fashion yielding large polymers. The reaction occurs between the adjacent monomers in the H‐bonded anti‐parallel stack, yielding pseudoprotein having a β‐meander structure. When dissolved in methanol, this pseudoprotein changes its secondary structure from β‐meander to α‐helical form and it retains the new secondary structure upon desolvation. This work demonstrates a novel paradigm for tuning the secondary structure of a polymer in the solid‐state.