ethyl N-tert-butoxycarbonyl-3,4-dimethoxyphenylalaninate | 128217-61-8

• 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: ethyl N-tert-butoxycarbonyl-3,4-dimethoxyphenylalaninate
• 英文别名: N-Boc-D,L-3,4-dimethoxyphenylalanine ethyl ester；ethyl 2-(N-(tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate；Ethyl 3-(3,4-dimethoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 128217-61-8
• 化学式: C₁₈H₂₇NO₆
• 分子量: 353.415
• InChiKey: WYLRQXNZQTZGNL-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  475.7±45.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl N-tert-butoxycarbonyl-3,4-dimethoxyphenylalaninate 在 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 ethyl 3-(3,4-dimethoxyphenyl)-2-(prop-2-enoxycarbonylamino)propanoate
  参考文献：
  名称：

  Synthesis of the chromophore of pseudobactin, a fluorescent siderophore from Pseudomonas

  摘要：

  DOI：

  10.1021/jo00301a008
• 作为产物：
  描述：

  ethyl (E)-3,4-dimethoxycinnamate 在 palladium on activated charcoal sodium azide 、 ammonium cerium(IV) nitrate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 ethyl N-tert-butoxycarbonyl-3,4-dimethoxyphenylalaninate
  参考文献：
  名称：

  Synthesis of Phenylalanine Analogs

  摘要：

  A straightforward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamic ester, followed by reaction with sodium acetate afforded the alpha-azidocinnamate in moderate yield. Hydrogenation of alpha-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.

  DOI：

  10.1002/jccs.200500150

文献信息

• Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation
  作者：Morgane Pigeaux、Romain Laporte、David C. Harrowven、Jérôme Baudoux、Jacques Rouden

  DOI：10.1016/j.tetlet.2016.09.001

  日期：2016.10

  Access to enantioenriched non-proteogenic phenylalanine derivatives is described using the enantioselective decarboxylative protonation reaction of amidohemimalonate esters catalysed by various cinchona-based compounds. This study compares the catalytic efficiency as well as the enantioselectivity induced by three types of common organocatalysts, namely thioureas, squaramides and bis-cinchona squaramides

  使用由各种基于金鸡纳的化合物催化的酰氨基半乳糖酸酯的对映选择性脱羧质子化反应，描述了获得对映体富集的非蛋白原性苯丙氨酸衍生物。这项研究比较了三种常见的有机催化剂（硫脲，方酸酰胺和双金鸡纳方酸酰胺）引起的催化效率以及对映选择性。这项工作的主要成果之一是观察到半棉酸盐的N-保护基团对其与催化剂相互作用的重大影响。在温和条件下进行的该方法具有良好的底物范围和官能团耐受性。在某些情况下，还可以使用亚化学计量的催化剂，同时提供良好的产率和选择性。
• Discovery of a Series of Nonpeptide Small Molecules That Inhibit the Binding of Insulin-like Growth Factor (IGF) to IGF-Binding Proteins
  作者：Chen、Yun-Fei Zhu、Xin-Jun Liu、Zi-Xian Lu、Qiu Xie、Nicholas Ling

  DOI：10.1021/jm010304b

  日期：2001.11.1

  Insulin-like growth factors (IGF-I and II) play an important role in metabolic and mitogenic activities through stimulation of the IGF-I receptor on the cell surface. Although the concentration of IGF in blood and cerebrospinal fluid is quite high (> 100 nM), this large pool of IGF is biologically inactive because of its association with six distinct binding proteins, which form high-affinity complexes with IGF. Thus, inhibitors of IGF-binding proteins (IGFBPs), especially IGFBP-3, could potentially alter the distribution between the "free" and "bound" forms of IGF and thereby elevate biologically active IGF-I to exert a beneficial effect on those patients with diseases that respond to the application of exogenous IGF-I. Whereas IGF-I peptide variants, which bind to IGFBPs but not the IGF-I receptor, have been shown to be potent IGF/IGFBP inhibitors, small molecule nonpeptide IGF/IGFBP inhibitors have the potential advantages of oral bioavailability and flexible dosing regimen. Here we report the discovery of several isoquinoline analogues, exemplified by I and 2, which bind IGFBP-3 as well as other IGFBPs at low nanomolar concentrations. More importantly, both compounds were shown to be able to release biologically active IGF-I from the IGF-I/IGFBP-3 complex. These results point to the feasibility of developing orally active therapeutics to treat IGF-responsive diseases by optimization of the lead molecules 1 and 2.
• KOLASA, TEODOZYJ;MILLER, MARVIN J., J. ORG. CHEM., 55,(1990) N4, C. 4246-4255
  作者：KOLASA, TEODOZYJ、MILLER, MARVIN J.

  DOI：——

  日期：——
• Synthesis of the chromophore of pseudobactin, a fluorescent siderophore from Pseudomonas
  作者：Teodozyj Kolasa、Marvin J. Miller

  DOI：10.1021/jo00301a008

  日期：1990.7
• Synthesis of Phenylalanine Analogs
  作者：Meng-Yang Chang、Chun-Yu Lin、Pei-Pei Sun

  DOI：10.1002/jccs.200500150

  日期：2005.10

  A straightforward synthesis of phenylalanine analogs is described. Cerium ammonium nitrate (CAN) mediated addition of azide to cinnamic ester, followed by reaction with sodium acetate afforded the alpha-azidocinnamate in moderate yield. Hydrogenation of alpha-azidocinnamate, followed by BOC, CBZ or Fmoc protection gave phenylalanine analogs. A new approach for synthesizing racemic p-boronophenylalanine analog was also explored.