3-phenyl-2-propynoylamino-propionic acid methyl ester | 904704-05-8

• 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: 3-phenyl-2-propynoylamino-propionic acid methyl ester
• 英文别名: Methyl 3-phenyl-2-(prop-2-ynoylamino)propanoate
• CAS: 904704-05-8
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: IKXLNXUABASHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-propynoylamino-propionic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以83%的产率得到Methyl 2-[[6-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]-6-oxohexa-2,4-diynoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  A mild copper-mediated Glaser-type coupling reaction under the novel CuI/NBS/DIPEA promoting system

  摘要：

  A simple copper promoting system CuI/NBS/DIPEA was first found to efficiently promote Glaser coupling reaction under ambient temperature. The alkynes with sensitive groups such as acetal and ketal, TBDMS, ester and amide could react smoothly to afford the functionalized 1,3-diynes under the CuI/NBS/DIPEA promoting system in good yields. And the successful application of the Cul/NBS/DIPEA promoting system in sugar and amino acid-building blocks indicated the potential of this method in the construction of designed sugar and peptide biomolecules. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.04.065
• 作为产物：
  描述：

  甲基 3-苯基-DL-丙氨酸酯 、 丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 生成 3-phenyl-2-propynoylamino-propionic acid methyl ester
  参考文献：
  名称：

  Allosteric Inhibitors of Macrophage Migration Inhibitory Factor (MIF) Interfere with Apoptosis-Inducing Factor (AIF) Co-Localization to Prevent Parthanatos

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00397

文献信息

• Palladium catalysed tandem cyclisation–anion capture. Part 8: Cascade hydrostannylation—cyclisation–anion capture and cascade hydroboration—cyclisation–anion capture on solid phase
  作者：Ronald Grigg、William S MacLachlan、David T MacPherson、Visuvanathar Sridharan、Selvaratnam Suganthan

  DOI：10.1016/s0040-4020(01)01061-4

  日期：2001.12

  five stereocentres are created, in five component processes (five point diversity), utilising resin bound aryl iodides by hydroboration or hydrostannylation of alkynes, followed by cyclisation–anion capture involving Suzuki or Stille reactions. Three small libraries were prepared to validate the chemistry.

  在五个组分过程（五点多样性）中，通过炔烃的硼氢化或加氢甲锡化利用树脂结合的芳基碘化物，然后进行涉及Suzuki或Stille反应的环化-阴离子捕获，可创建多达四个键和五个立体中心。准备了三个小型文库以验证化学性质。
• Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition
  作者：Johan Tejler、Erik Tullberg、Torbjörn Frejd、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1016/j.carres.2006.04.028

  日期：2006.7

  Acetylene derivatives of phenylalanine, phenethylamine and the multifunctional unnatural amino acids, phenyl-bis-alanine and phenyl-tris-alanine, were synthesized and functionalized with 2-azidoethyl beta-D-galactopyranosyl-(1 -> 4)-beta-D-glucopyranoside via regioselective copper(I)-mediated 1,3-dipolar cycloaddition to give a panel of mono-, di- and trivalent lactoside derivatives. Evaluation of the compounds as inhibitors against the tumour- and inflammation-related galectin-1, -3, 4N, 4C, -4, -7, -8N and -9N revealed a divalent compound with a K-d value as low as 3.2 mu M for galectin-1, which corresponded to a relative potency of 30 per lactose unit as compared to the natural disaccharide ligand lactose. This divalent compound had at least one order of magnitude higher affinity for galectin-1 than for any of the other galectins investigated. (c) 2006 Elsevier Ltd. All rights reserved.