ethyl 2,3-bis(3,4-dimethoxyphenyl)-3-oxopropanoate | 167167-93-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: ethyl 2,3-bis(3,4-dimethoxyphenyl)-3-oxopropanoate
• CAS: 167167-93-3
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: YIHDCFJTFLRIIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-bis(3,4-dimethoxyphenyl)-3-oxopropanoate 在 lithium aluminium tetrahydride 、 zinc(II) tetrahydroborate 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (4R^*,5S^*)-4,5-bis-(3,4-dimethoxyphenyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis of DL-threo-3-(1-fluoro-1-methylethyl)- and DL-threo-3-(1,1-difluoroethyl)malic acids. Mechanistic studies of 3-isopropylmalate dehydrogenase

  摘要：

  For both mechanistic studies and the development of novel inhibitors of 3-isopropylmalate dehydrogenase enzyme (IPMDH), which is involved in the rate-determining step in the biosynthetic pathway of the essential amino acid L-leucine, (2R*,3S*)-3-(1-fluoro-1-methylethyl)- and (2R*,3S*)-3-(1,1-difluoroethyl)malic acids (F-IPM and F-2-EM) were designed based on the concept of mechanism-based inhibition, and the reaction kinetics with these fluorinated substrates were analysed, The reaction of F-IPM with IPMDH was studied by NMR spectroscopy and product isolation. F-IPM underwent, after the normal enzyme reaction, the expected additional elimination reaction to afford an alpha,beta-unsaturated carbonyl product, which turned out not to participate in any covalent-bond-forming reaction. The conformation of the reaction intermediate during the IPMDH reaction and the functional-group arrangement in the active site of IPMDH are discussed.

  DOI：

  10.1039/p19950001905
• 作为产物：
  描述：

  3,4-二甲氧基苯基乙酸乙酯 、 3,4-二甲氧基苯甲酸乙酯 在 sodium hydride 作用下， 生成 ethyl 2,3-bis(3,4-dimethoxyphenyl)-3-oxopropanoate
  参考文献：
  名称：

  Synthesis of DL-threo-3-(1-fluoro-1-methylethyl)- and DL-threo-3-(1,1-difluoroethyl)malic acids. Mechanistic studies of 3-isopropylmalate dehydrogenase

  摘要：

  For both mechanistic studies and the development of novel inhibitors of 3-isopropylmalate dehydrogenase enzyme (IPMDH), which is involved in the rate-determining step in the biosynthetic pathway of the essential amino acid L-leucine, (2R*,3S*)-3-(1-fluoro-1-methylethyl)- and (2R*,3S*)-3-(1,1-difluoroethyl)malic acids (F-IPM and F-2-EM) were designed based on the concept of mechanism-based inhibition, and the reaction kinetics with these fluorinated substrates were analysed, The reaction of F-IPM with IPMDH was studied by NMR spectroscopy and product isolation. F-IPM underwent, after the normal enzyme reaction, the expected additional elimination reaction to afford an alpha,beta-unsaturated carbonyl product, which turned out not to participate in any covalent-bond-forming reaction. The conformation of the reaction intermediate during the IPMDH reaction and the functional-group arrangement in the active site of IPMDH are discussed.

  DOI：

  10.1039/p19950001905

文献信息

• Synthesis of DL-threo-3-(1-fluoro-1-methylethyl)- and DL-threo-3-(1,1-difluoroethyl)malic acids. Mechanistic studies of 3-isopropylmalate dehydrogenase
  作者：Tetsuya Aoyama、Tadashi Eguchi、Tairo Oshima、Katsumi Kakinuma

  DOI：10.1039/p19950001905

  日期：——

  For both mechanistic studies and the development of novel inhibitors of 3-isopropylmalate dehydrogenase enzyme (IPMDH), which is involved in the rate-determining step in the biosynthetic pathway of the essential amino acid L-leucine, (2R*,3S*)-3-(1-fluoro-1-methylethyl)- and (2R*,3S*)-3-(1,1-difluoroethyl)malic acids (F-IPM and F-2-EM) were designed based on the concept of mechanism-based inhibition, and the reaction kinetics with these fluorinated substrates were analysed, The reaction of F-IPM with IPMDH was studied by NMR spectroscopy and product isolation. F-IPM underwent, after the normal enzyme reaction, the expected additional elimination reaction to afford an alpha,beta-unsaturated carbonyl product, which turned out not to participate in any covalent-bond-forming reaction. The conformation of the reaction intermediate during the IPMDH reaction and the functional-group arrangement in the active site of IPMDH are discussed.