(R)-2-[(E)-3-(2,4-Dimethoxy-phenyl)-acryloylamino]-3-methyl-butyric acid ethyl ester | 186261-39-2

• 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: (R)-2-[(E)-3-(2,4-Dimethoxy-phenyl)-acryloylamino]-3-methyl-butyric acid ethyl ester
• 英文别名: ethyl (2R)-2-[[(E)-3-(2,4-dimethoxyphenyl)prop-2-enoyl]amino]-3-methylbutanoate
• CAS: 186261-39-2
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: PBCYGAADFBLXDU-SYJIQKIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-[(E)-3-(2,4-Dimethoxy-phenyl)-acryloylamino]-3-methyl-butyric acid ethyl ester 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 ethyl (2R)-3-methyl-2-[[2-[8,14,20-tris[2-[[(2R)-1-ethoxy-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]-4,6,10,12,16,18,22,24-octamethoxy-2-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl]acetyl]amino]butanoate
  参考文献：
  名称：

  Synthesis of C-Alkylcalix[4]arenes. 4. Design, Synthesis, and Computational Studies of Novel Chiral Amido[4]resorcinarenes

  摘要：

  In extending our studies involving BF3-Et(2)O-catalyzed reaction of cinnamic acid analogues, we have shown that amido derivatives also can afford [4]resorcinarene octamethyl ethers. Subsequently, chiral monomeric amides, derived from the mixed anhydride of cinnamic acid and L- or D-valine, upon treatment with BF3-Et(2)O, yielded for the first time chiral amido [4]resorcinarenes in enantiomerically pure forms. Four stereoisomers were isolated, and three of them were attributed the flattened-cone, chair, and 1,2-alternate conformations. The major product was assigned a novel chairlike structure, namely flattened partial cone 1. The flattened-cone stereoisomer which was indicated by molecular modeling studies to be the most stable, became the major product under more drastic experimental conditions. Chromatographic studies an chiral phases revealed that the above tetramers could be used for the enantiodiscrimination of racemic molecules.

  DOI：

  10.1021/jo962018r
• 作为产物：
  描述：

  (2R)-2-氨基-3-甲基丁酸盐酸盐 在 氯化亚砜 、 氯磷酸二乙酯 、 三乙胺 作用下， 反应 9.0h， 生成 (R)-2-[(E)-3-(2,4-Dimethoxy-phenyl)-acryloylamino]-3-methyl-butyric acid ethyl ester
  参考文献：
  名称：

  Synthesis of C-Alkylcalix[4]arenes. 4. Design, Synthesis, and Computational Studies of Novel Chiral Amido[4]resorcinarenes

  摘要：

  In extending our studies involving BF3-Et(2)O-catalyzed reaction of cinnamic acid analogues, we have shown that amido derivatives also can afford [4]resorcinarene octamethyl ethers. Subsequently, chiral monomeric amides, derived from the mixed anhydride of cinnamic acid and L- or D-valine, upon treatment with BF3-Et(2)O, yielded for the first time chiral amido [4]resorcinarenes in enantiomerically pure forms. Four stereoisomers were isolated, and three of them were attributed the flattened-cone, chair, and 1,2-alternate conformations. The major product was assigned a novel chairlike structure, namely flattened partial cone 1. The flattened-cone stereoisomer which was indicated by molecular modeling studies to be the most stable, became the major product under more drastic experimental conditions. Chromatographic studies an chiral phases revealed that the above tetramers could be used for the enantiodiscrimination of racemic molecules.

  DOI：

  10.1021/jo962018r

文献信息

• Synthesis of <i>C</i>-Alkylcalix[4]arenes. 4. Design, Synthesis, and Computational Studies of Novel Chiral Amido[4]resorcinarenes
  作者：Bruno Botta、Giuliano Delle Monache、Patrizia Salvatore、Francesco Gasparrini、Claudio Villani、Maurizio Botta、Federico Corelli、Andrea Tafi、Eszter Gacs-Baitz、Antonello Santini、Cristopher F. Carvalho、Domenico Misiti

  DOI：10.1021/jo962018r

  日期：1997.2.1

  In extending our studies involving BF3-Et(2)O-catalyzed reaction of cinnamic acid analogues, we have shown that amido derivatives also can afford [4]resorcinarene octamethyl ethers. Subsequently, chiral monomeric amides, derived from the mixed anhydride of cinnamic acid and L- or D-valine, upon treatment with BF3-Et(2)O, yielded for the first time chiral amido [4]resorcinarenes in enantiomerically pure forms. Four stereoisomers were isolated, and three of them were attributed the flattened-cone, chair, and 1,2-alternate conformations. The major product was assigned a novel chairlike structure, namely flattened partial cone 1. The flattened-cone stereoisomer which was indicated by molecular modeling studies to be the most stable, became the major product under more drastic experimental conditions. Chromatographic studies an chiral phases revealed that the above tetramers could be used for the enantiodiscrimination of racemic molecules.