methyl (2S)-2-(furan-2-carbonylamino)-3-phenylpropanoate

• 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 (2S)-2-(furan-2-carbonylamino)-3-phenylpropanoate
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: KAEMXHWSGSEIMR-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-(furan-2-carbonylamino)-3-phenylpropanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以1.25 g的产率得到(S)-2-(furan-2-carboxamido)-3-phenylpropanoic acid
  参考文献：
  名称：

  A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics

  摘要：

  We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.

  DOI：

  10.1055/s-0033-1339550
• 作为产物：
  描述：

  糠酸（呋喃甲酸） 、 L-苯丙氨酸甲酯盐酸盐 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78 %的产率得到methyl (2S)-2-(furan-2-carbonylamino)-3-phenylpropanoate
  参考文献：
  名称：

  铜催化选择性 C-O/C-N 环化化学发散合成恶唑和咪唑烷酮

  摘要：

  苯丙氨酸衍生的恶唑和咪唑烷酮的有效合成可以通过铜催化反应来实现，这些反应由导向基团控制并通过选择性 C-O 或 C-N 偶联进行。该策略采用廉价的商业铜催化剂和容易获得的起始材料。它使用方便的反应程序，为杂环结构单元的多功能和灵活组装提供了可靠的方法。

  DOI：

  10.1021/acs.joc.3c00505

文献信息

• A Convenient and Efficient Synthesis of Dipeptidyl Benzoxaboroles and Their Peptidomimetics
  作者：Zhengyan Fu、Yongmei Xie、Jiangpeng He、Aiping Tong、Yuquan Wei

  DOI：10.1055/s-0033-1339550

  日期：——

  We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl)phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3-phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules.