methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate | 289665-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate
• CAS: 289665-41-4
• 化学式: C₁₁H₁₁NO₆
• 分子量: 253.211
• InChiKey: IFHYQURVCKZWFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate 在 palladium on activated charcoal silver imidazolate 、 氢气 、 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 2-amino-3-(β-D-glucopyranosyloxy)-γ-oxobenzenebutanoic acid
  参考文献：
  名称：

  Total Synthesis of α-Deamino-3-(β- d -glucopyranosyloxy)kynurenine

  摘要：

  alpha-Deamino-3-(beta-D-glucopyranosyloxy)krynurenine a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylation of methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate followed by reduction of the nitro group and deprotection. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00285-4
• 作为产物：
  描述：

  4-(3-甲氧基-2-硝基苯基)-4-氧代丁酸 在 三氟化硼乙醚 、 lithium chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate
  参考文献：
  名称：

  Total Synthesis of α-Deamino-3-(β- d -glucopyranosyloxy)kynurenine

  摘要：

  alpha-Deamino-3-(beta-D-glucopyranosyloxy)krynurenine a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylation of methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate followed by reduction of the nitro group and deprotection. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00285-4

文献信息

• Total Synthesis of α-Deamino-3-(β- d -glucopyranosyloxy)kynurenine
  作者：H.Keith Chenault、Jie Yang、Douglass F. Taber

  DOI：10.1016/s0040-4020(00)00285-4

  日期：2000.6

  alpha-Deamino-3-(beta-D-glucopyranosyloxy)krynurenine a yellow, fluorescent compound isolated from human lens, was synthesized in 8 steps (10% overall yield) from commercially available 3-methoxy-2-nitrobenzaldehyde. Key events included preparation and glucosylation of methyl 4-(3-hydroxy-2-nitrophenyl)-4-oxobutanoate followed by reduction of the nitro group and deprotection. (C) 2000 Elsevier Science Ltd. All rights reserved.