氧代(丙基氨基)乙酸 | 81682-53-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 氧代(丙基氨基)乙酸
• 中文别名: 2-氧代-2-丙基氨基-乙酸
• 英文名称: N-propyloxamic acid
• 英文别名: Oxo(propylamino)acetic acid；2-oxo-2-(propylamino)acetic acid
• CAS: 81682-53-3
• 化学式: C₅H₉NO₃
• mdl: MFCD09971257
• 分子量: 131.131
• InChiKey: HHQMZOFGKZVJDE-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: chloroform (67-66-3))
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  氧代(丙基氨基)乙酸 在 copper diacetate 、 silver nitrate ammonium peroxydisulfate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以73%的产率得到异氰酸丙酯
  参考文献：
  名称：

  Reactivity of Carbamoyl Radicals. A New, General, Convenient Free-Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid

  摘要：

  A new, general, simple synthesis of isocyanates was developed by oxidation of monoamides of oxalic acid with peroxydisulfate catalyzed by Ag and Cu salts. The reaction was carried out in a two-phase system (water and an organic solvent), and it is suitable also for practical applications, due to the simple experimental conditions and the inexpensive as well as nontoxic reagents. The first example of homolytic intramolecular aromatic carbamoylation is also reported.

  DOI：

  10.1021/jo00122a020
• 作为产物：
  描述：

  methyl 2-oxo-2-(propylamino) acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 氧代(丙基氨基)乙酸
  参考文献：
  名称：

  Reactivity of Carbamoyl Radicals. A New, General, Convenient Free-Radical Synthesis of Isocyanates from Monoamides of Oxalic Acid

  摘要：

  A new, general, simple synthesis of isocyanates was developed by oxidation of monoamides of oxalic acid with peroxydisulfate catalyzed by Ag and Cu salts. The reaction was carried out in a two-phase system (water and an organic solvent), and it is suitable also for practical applications, due to the simple experimental conditions and the inexpensive as well as nontoxic reagents. The first example of homolytic intramolecular aromatic carbamoylation is also reported.

  DOI：

  10.1021/jo00122a020

文献信息

• Palladium-catalyzed decarboxylative <i>ortho</i>-amidation of <i>O</i>-methyl ketoximes with oxamic acids
  作者：Kun Jing、Peng-Cheng Cui、Guan-Wu Wang

  DOI：10.1039/c9cc06460e

  日期：——

  The first palladium-catalyzed ortho-amidation of ketoximes has been developed with readily available, easy to handle and environment-friendly N,N-disubstituted oxamic acids as the amidation sources. When N-monosubstituted oxamic acids are used as the substrates, the formed ortho-amidated ketoximes undergo further intramolecular cyclization to provide 3-methyleneisoindolinones.

  第一钯催化邻酮肟-amidation已经开发了现成的，容易处理和环境友好型ñ，ñ二取代草氨酸作为酰胺化的来源。当使用N-单取代的草酰胺酸作为底物时，形成的邻酰胺化的酮肟进一步进行分子内环化以提供3-亚甲基异吲哚啉酮。
• Synthesis, Crystal Structure, and Insecticidal Activity of Novel <i>N</i>-Alkyloxyoxalyl Derivatives of 2-Arylpyrrole
  作者：Yu Zhao、Chunhui Mao、Yongqiang Li、Pengxiang Zhang、Zhiqiang Huang、Fuchun Bi、Runqiu Huang、Qingmin Wang

  DOI：10.1021/jf801311h

  日期：2008.8.1

  Two series of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole were synthesized, and their structures were characterized by (1)H NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal activities, and their insecticidal activities against oriental armyworm, mosquito, and spider mite are comparable to those of the commercialized Chlorfenapyr.
• Hydrogen bond patterns in solid state carboxylic acids. Vibrational behaviour of the catamer pattern as exhibited by the N-alkyloxamic acids
  作者：Ilse Wolfs、Herman O. Desseyn

  DOI：10.1016/0584-8539(96)01689-3

  日期：1996.10

  The vibrational study presented in this publication shows that the N-alkyloxamic acids are hydrogen bonded through a catamer hydrogen bond pattern in the solid state. Two different hydrogen bond patterns are possible for these products, and these patterns can be very clearly distinguished by their vibrational behaviour. Deuteration and low temperature spectra make the assignment and characterisation more obvious.
• Oxamic acid analogues as LDH-C4-specific competitive inhibitors
  作者：Lorena Rodríguez-Páez、Miguel Angel Chena-Taboada、Arturo Cabrera-Hernández、Joaquín Cordero-Martínez、Carlos Wong

  DOI：10.3109/14756366.2011.566221

  日期：2011.8.1

  We performed kinetic studies to determine whether oxamate analogues are selective inhibitors of LDH-C4, owing to their potential usefulness in fertility control and treatment of some cancers. These substances were shown to be competitive inhibitors of LDH isozymes and are able to discriminate among subtle differences that differentiate the active sites of LDH-A4, LDH-B4 and LDH-C4. N-Ethyl oxamate was the most potent inhibitor showing the highest affinity for LDH-C4. However, N-propyl oxamate was the most selective inhibitor showing a high degree of selectivity towards LDH-C4. Non-polar four carbon atoms chains, linear or branched, dramatically diminished the affinity and selectivity towards LDH-C4. N-Propyl oxamate significantly reduced ATP levels, capacitation and mouse sperm motility, in line with results shown by others, suggesting that LDH-C4 plays an essential role in mouse fertility.
• Reactions of Dehydroascorbic Acid with Primary Aliphatic Amines Including <i>N</i>^α-Acetyllysine
  作者：Bernd Larisch、Monika Pischetsrieder、Theodor Severin

  DOI：10.1021/jf9601426

  日期：1996.1.1

  The reaction of L-debydroascorbic acid (DHA) with primary aliphatic amines including N-alpha-acetyllysine was examined by HPLC A new aminoreductone, 2-deoxy-2-(propylamino)ascorbic acid (1) was isolated and the structure elucidated by spectroscopic data. Furthermore oxalic acid mono-(2) and diamides (3) were identified as important degradation products of DHA under Maillard conditions, 3-Deoxy-3-(alkylamino)ascorbic acids (4), typical condensation products of L-ascorbic acid and amines, were also detected in the reaction mixtures of DHA. All produces are formed under oxidative and nonoxidative conditions from DHA.