2-((Z)-2,4-dinitro-phenylhydrazono)-propionic acid methyl ester | 62740-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((Z)-2,4-dinitro-phenylhydrazono)-propionic acid methyl ester
• 英文别名: 2-((Z)-2,4-Dinitro-phenylhydrazono)-propionsaeure-methylester；Brenztraubensaeuremethylester-2,4-dinitrophenylhydrazon；methyl (2Z)-2-[(2,4-dinitrophenyl)hydrazinylidene]propanoate
• CAS: 62740-61-8
• 化学式: C₁₀H₁₀N₄O₆
• 分子量: 282.213
• InChiKey: CJGSUGQCFVSSAY-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(2,4-dinitrophenylhydrazono)-propanoic acid 在 氯化亚砜 作用下， 生成 2-((Z)-2,4-dinitro-phenylhydrazono)-propionic acid methyl ester
  参考文献：
  名称：

  van Duin, Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 68,71

  摘要：

  DOI：

文献信息

• Metabolism of 4-Amino-3-hydroxybenzoic Acid by<i>Bordetella</i>sp. Strain 10d: A Different Modified<i>Meta</i>-Cleavage Pathway for 2-Aminophenols
  作者：Chika ORII、Shinji TAKENAKA、Shuichiro MURAKAMI、Kenji AOKI

  DOI：10.1271/bbb.60264

  日期：2006.11.23

  Bordetella sp. strain 10d metabolizes 4-amino-3-hydroxybenzoic acid via 2-hydroxymuconic 6-semialdehyde. Cell extracts from 4-amino-3-hydroxybenzoate-grown cells showed high NAD+-dependent 2-hydroxymuconic 6-semialdehyde dehydrogenase, 4-oxalocrotonate tautomerase, 4-oxalocrotonate decarboxylase, and 2-oxopent-4-enoate hydratase activities, but no 2-hydroxymuconic 6-semialdehyde hydrolase activity. These enzymes involved in 4-amino-3-hydroxybenzoate metabolism were purified and characterized. When 2-hydroxymuconic 6-semialdehyde was used as substrate in a reaction mixture containing NAD+ and cell extracts from 4-amino-3-hydroxybenzoate-grown cells, 4-oxalocrotonic acid, 2-oxopent-4-enoic acid, and 4-hydroxy-2-oxovaleric acid were identified as intermediates, and pyruvic acid was identified as the final product. A complete pathway for the metabolism of 4-amino-3-hydroxybenzoic acid in strain 10d is proposed. Strain 10d metabolized 2-hydroxymuconic 6-semialdehyde derived from 4-amino-3-hydroxybenzoic acid via a dehydrogenative route, not via a hydrolytic route. This proposed metabolic pathway differs considerably from the modified meta-cleavage pathway of 2-aminophenol and those previously reported for methyl- and chloro-derivatives.

  Bordetella sp. 10d株通过2-羟基穆康酸6-半醛代谢4-氨基-3-羟基苯甲酸。来自于培养于4-氨基-3-羟基苯甲酸的细胞的细胞提取物显示出高水平的NAD+-依赖性2-羟基穆康酸6-半醛脱氢酶、4-草酰克罗通酸互变异构酶、4-草酰克罗通酸脱羧酶和2-氧戊-4-烯酸水合酶活性，但没有检测到2-羟基穆康酸6-半醛水解酶活性。这些参与4-氨基-3-羟基苯甲酸代谢的酶被纯化并进行了特征分析。当在含有NAD+和来自于4-氨基-3-羟基苯甲酸的细胞提取物的反应混合物中使用2-羟基穆康酸6-半醛作为底物时，4-草酰克罗通酸、2-氧戊-4-烯酸和4-羟基-2-氧戊酸被鉴定为中间产物，而丙酮酸被鉴定为最终产物。提出了10d株对4-氨基-3-羟基苯甲酸的完整代谢途径。10d株通过脱氢途径代谢由4-氨基-3-羟基苯甲酸衍生的2-羟基穆康酸6-半醛，而不是通过水解途径。这种提议的代谢途径与2-氨基酚的改良元断裂途径以及之前报道的甲基和氯衍生物的途径有显著不同。
• Studies concerning the antibiotic actinonin. Part II. Total synthesis of actinonin and some structural analogues by the isomaleimide method
  作者：Nicholas H. Anderson、W. David Ollis、John E. Thorpe、A. David Ward

  DOI：10.1039/p19750000825

  日期：——

  A general method for the synthesis of actinonin (I) and several structural analogues is described. L-Valyl-L-prolinol (III) and the isomaleimide (XIV) yield the intermediate (XVII), which gives actinonin (I) on hydrogenation. Corresponding routes yield compounds (XXV)(L-alanylpyrrolidine and DL-alanylpyrrolidine analogues), (XXVI)(L-valylpyrrolidine analogue), and (XXVII)(L-valyl-L-prolinol analogue)

  描述了合成肌动蛋白（I）和几种结构类似物的一般方法。L-戊基-L-脯氨醇（III）和异马来酰亚胺（XIV）产生中间体（XVII），其在氢化时产生肌动蛋白（I）。相应的路线产生化合物（XXV）（L-丙氨酰吡咯烷和DL-丙氨酰吡咯烷类似物），（XXVI）（L-戊吡咯烷类似物）和（XXVII）（L- valyl- L-脯氨醇类似物），是缺乏戊基侧链的肌动蛋白类似物。