methyl (S)-2-acetamido-3-(4-(benzyloxy)phenyl)propanoate | 39613-68-8

• 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: methyl (S)-2-acetamido-3-(4-(benzyloxy)phenyl)propanoate
• 英文别名: methyl (2S)-2-acetamido-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 39613-68-8
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: AQQXVKQWGGPPHH-SFHVURJKSA-N

物化性质

• 沸点：
  523.1±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-acetamido-3-(4-(benzyloxy)phenyl)propanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 N-乙酰-L-酪氨酸甲酯
  参考文献：
  名称：

  Preparation of diaryl ethers from tyrosine or 4-hydroxyphenylglycine using organomanganese chemistry

  摘要：

  DOI：

  10.1021/jo00361a043
• 作为产物：
  描述：

  Boc-L-酪氨酸甲酯 在 sodium carbonate 、 potassium carbonate 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 15.0h， 生成 methyl (S)-2-acetamido-3-(4-(benzyloxy)phenyl)propanoate
  参考文献：
  名称：

  Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold

  摘要：

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.014

文献信息

• Easy access to drug building-blocks through benzylic C–H functionalization of phenolic ethers by photoredox catalysis
  作者：Tobias Brandhofer、Martin Stinglhamer、Volker Derdau、María Méndez、Christoph Pöverlein、Olga García Mancheño

  DOI：10.1039/d1cc01756j

  日期：——

  A visible light-mediated photocatalyzed C–C-bond forming method for the benzylic C–H functionalization of phenolether containing synthetic building blocks based on a radical-cation/deprotonation strategy is reported. This method allows the mild, selective generation of benzyl radicals in phenolic complex molecules and drug-like compounds, providing new entries in synthetic and medicinal chemistry.

  报道了一种基于自由基阳离子/去质子化策略的可见光介导的光催化 C - C 键形成方法，用于含合成结构单元的苯酚醚的苄基 C-H 官能化。该方法允许在酚类复合物分子和类药物化合物中温和、选择性地生成苄基，为合成和药物化学提供了新的入口。
• Proline-rich proteins—deriving a basis for residue-based selectivity in polyphenolic binding
  作者：A. K. Croft、M. K. Foley

  DOI：10.1039/b800365c

  日期：——

  1H NMR titration experiments have been used to establish that minimal proline-based models show enhanced binding selectivity towards phenol in CDCl3, relative to other similarly protected amino acid residues. Cooperative binding effects appear to play a role, with sarcosine models affording binding constants to phenol intermediate to those obtained from proline models and other amino acid models. The mechanism for binding, based on DFT calculations and the application of Hunter's molecular recognition toolbox model, cannot be solely attributed to hydrogen bond strength, and appears to be mediated through C–H-π bonds and the rotational freedom of the amide substrate.

  1H NMR 滴定实验证明，相对于其他类似的受保护氨基酸残基，基于脯氨酸的最小模型在 CDCl3 中对苯酚的结合选择性更强。协同结合效应似乎在其中发挥了作用，肌氨酸模型与苯酚的结合常数介于脯氨酸模型和其他氨基酸模型得到的结合常数之间。根据 DFT 计算和亨特分子识别工具箱模型的应用，结合机制不能完全归因于氢键强度，而似乎是通过 CâH-Ï 键和酰胺底物的旋转自由度介导的。
• 10.1021/acs.joc.4c00988
  作者：Bag, Raghunath、Sharma, Nagendra K.

  DOI：10.1021/acs.joc.4c00988

  日期：——

  a Pd-catalyzed picolinamide-directed site-selective C(sp2)–H sulfonylation of amino acids and peptides with sodium sulfinates in moderate to good yields. Sulfonylation of levodopa and dopamine drug molecules and late-stage directed peptide sulfonylation are studied for the first time. Broad substrate scope having various functionalities, late-stage drug modifications, and various post synthetic utilities

  本报告描述了 Pd 催化的吡啶甲酰胺定向位点选择性 C（sp2）-H 氨基酸和肽与亚磺酸钠的磺酰化反应，产率中等至良好。首次研究了左旋多巴和多巴胺药物分子的磺酰化以及晚期定向肽磺酰化。潜在的优势包括具有各种功能的广泛底物范围、后期药物修饰以及各种合成后实用程序，如硫属化、溴化、烯化和芳基化。
• Preparation of diaryl ethers from tyrosine or 4-hydroxyphenylglycine using organomanganese chemistry
  作者：Anthony J. Pearson、Paul R. Bruhn、Shih Ying Hsu

  DOI：10.1021/jo00361a043

  日期：1986.5
• Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold
  作者：Xian-Chao Cheng、Run-Ling Wang、Zhen-Ke Dong、Jing Li、Yao-Yuan Li、Rong-Rong Li

  DOI：10.1016/j.bmc.2012.08.014

  日期：2012.10

  A series of novel L-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these L-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 +/- 0.001 mu M) and 6j (IC50 = 0.017 +/- 0.001 mu M) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 +/- 0.001 mu M). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC50 = 3.6 +/- 0.2 mu M) and 6c (IC50 = 5.8 +/- 0.5 mu M), were equal potent to the positive control SAHA (IC50 = 1.6 +/- 0.1 mu M). Structure-activity relationships were also briefly discussed. (C) 2012 Elsevier Ltd. All rights reserved.