ethyl 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydropyridine-3-carboxylate | 38532-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydropyridine-3-carboxylate
• 英文别名: 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester；Ethyl 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydro-3-pyridinecarboxylate；ethyl 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenylpyridine-3-carboxylate
• CAS: 38532-90-0
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: SKTQHUYUHXWJRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydropyridine-3-carboxylate 在 sodium hydroxide 作用下， 以 二苯醚 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 1-benzyl-4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  烯醇导向的铑（III）催化的C ？的对映选择性合成螺二烯 H功能化和螺环化

  摘要：

  手性环戊二烯基铑配合物可促进高度对映体选择性的烯醇导向的C（sp 2）-H功能化和炔烃的氧化环化反应，从而得到含有全碳四元立体中心的螺茚。两个可能的导向基团之间的高选择性以及在O结合的烯醇铑铑到C结合的异构体的异构化过程中的旋转方向控制对于高对映体过量至关重要。

  DOI：

  10.1002/anie.201507029
• 作为产物：
  描述：

  二(2,4,6-三氯苯基)苯基丙二酸酯 、 (E)-3-Benzylamino-but-2-enoic acid ethyl ester 以 various solvent(s) 为溶剂， 反应 1.0h， 以77%的产率得到ethyl 1-benzyl-4-hydroxy-2-methyl-6-oxo-5-phenyl-1,6-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones

  摘要：

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.

  DOI：

  10.1016/0223-5234(91)90194-r

文献信息

• Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones
  作者：G Dannhardt、W Meindl、BD Schober、T Kappe

  DOI：10.1016/0223-5234(91)90194-r

  日期：1991.9

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.
• Enantioselective Synthesis of Spiroindenes by Enol‐Directed Rhodium(III)‐Catalyzed CH Functionalization and Spiroannulation
  作者：Suresh Reddy Chidipudi、David J. Burns、Imtiaz Khan、Hon Wai Lam

  DOI：10.1002/anie.201507029

  日期：2015.11.16

  rhodium complexes promote highly enantioselective enol‐directed C(sp2)‐H functionalization and oxidative annulation with alkynes to give spiroindenes containing all‐carbon quaternary stereocenters. High selectivity between two possible directing groups, as well as control of the direction of rotation in the isomerization of an O‐bound rhodium enolate into the C‐bound isomer, appear to be critical for high

  手性环戊二烯基铑配合物可促进高度对映体选择性的烯醇导向的C（sp 2）-H功能化和炔烃的氧化环化反应，从而得到含有全碳四元立体中心的螺茚。两个可能的导向基团之间的高选择性以及在O结合的烯醇铑铑到C结合的异构体的异构化过程中的旋转方向控制对于高对映体过量至关重要。