N-(methoxycarbonyl)-3-<(methoxymethyl)oxy>aniline | 136247-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(methoxycarbonyl)-3-<(methoxymethyl)oxy>aniline
• 英文别名: methyl N-[3-(methoxymethoxy)phenyl]carbamate
• CAS: 136247-91-1
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: VGPHUGXSEHIVDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(methoxycarbonyl)-3-<(methoxymethyl)oxy>aniline 、 氯甲酸甲酯 在 叔丁基锂 作用下， 生成 methyl 2-(methoxycarbonylamino)-4-(methoxymethoxy)benzoate 、 methyl 2-(methoxycarbonylamino)-6-(methoxymethoxy)benzoate
  参考文献：
  名称：

  Studies on nitrogen metabolism using carbon-13 NMR spectroscopy. 6. Biosynthesis of sarubicin A. Synthesis and incorporation of 6-hydroxy[13CO15NH2]anthranilamide

  摘要：

  We have previously demonstrated that 6-hydroxyanthranilic acid (3) is specifically incorporated into sarubicin A (1) by Streptomyces helicus. 6-Hydroxyanthranilamide (4) has now been synthesized in five steps from m-anisidine in a manner that allowed efficient introduction of isotope labels to prepare [(CONH2)-C-13-N-15]-4a. A new synthesis of 3 from m-anisidine has also been developed. 4a was fed to S. helicus, and a 1.29% incorporation into 1b was obtained. Examination of the C-13 NMR spectrum of 1b revealed predominantly intact incorporation, with a minor amount of 4a (0.13%) first undergoing in vivo hydrolysis to the corresponding acid. Thus, carboxamide formation is the next step in the biosynthesis of 1.

  DOI：

  10.1021/jo00023a036
• 作为产物：
  描述：

  3-氨基苯酚 在 sodium hydride 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 N-(methoxycarbonyl)-3-<(methoxymethyl)oxy>aniline
  参考文献：
  名称：

  Studies on nitrogen metabolism using carbon-13 NMR spectroscopy. 6. Biosynthesis of sarubicin A. Synthesis and incorporation of 6-hydroxy[13CO15NH2]anthranilamide

  摘要：

  We have previously demonstrated that 6-hydroxyanthranilic acid (3) is specifically incorporated into sarubicin A (1) by Streptomyces helicus. 6-Hydroxyanthranilamide (4) has now been synthesized in five steps from m-anisidine in a manner that allowed efficient introduction of isotope labels to prepare [(CONH2)-C-13-N-15]-4a. A new synthesis of 3 from m-anisidine has also been developed. 4a was fed to S. helicus, and a 1.29% incorporation into 1b was obtained. Examination of the C-13 NMR spectrum of 1b revealed predominantly intact incorporation, with a minor amount of 4a (0.13%) first undergoing in vivo hydrolysis to the corresponding acid. Thus, carboxamide formation is the next step in the biosynthesis of 1.

  DOI：

  10.1021/jo00023a036

文献信息

• Studies on nitrogen metabolism using carbon-13 NMR spectroscopy. 6. Biosynthesis of sarubicin A. Synthesis and incorporation of 6-hydroxy[13CO15NH2]anthranilamide
  作者：Steven J. Gould、Rodney L. Eisenberg

  DOI：10.1021/jo00023a036

  日期：1991.11

  We have previously demonstrated that 6-hydroxyanthranilic acid (3) is specifically incorporated into sarubicin A (1) by Streptomyces helicus. 6-Hydroxyanthranilamide (4) has now been synthesized in five steps from m-anisidine in a manner that allowed efficient introduction of isotope labels to prepare [(CONH2)-C-13-N-15]-4a. A new synthesis of 3 from m-anisidine has also been developed. 4a was fed to S. helicus, and a 1.29% incorporation into 1b was obtained. Examination of the C-13 NMR spectrum of 1b revealed predominantly intact incorporation, with a minor amount of 4a (0.13%) first undergoing in vivo hydrolysis to the corresponding acid. Thus, carboxamide formation is the next step in the biosynthesis of 1.