2-amino-2-formylacetic acid | 5735-66-0

• 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
• 英文名称: 2-amino-2-formylacetic acid
• 英文别名: α-formylglycine；3-Oxoalanine；2-amino-3-oxopropanoic acid
• CAS: 5735-66-0
• 化学式: C₃H₅NO₃
• mdl: MFCD19204727
• 分子量: 103.078
• InChiKey: XMTCKNXTTXDPJX-UHFFFAOYSA-N

物化性质

• 沸点：
  270.7±35.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为产物：
  描述：

  DL-丝氨酸 在 [Cp*Rh(2,2'-bipyridine)(OH)]+ 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 2-amino-2-formylacetic acid
  参考文献：
  名称：

  Oxidation of Alcohols by [Cp*Rh( ppy)(OH)]+

  摘要：

  Rh(III) polypyridine complexes ([Cp*Rh(ppy)(H2O)(2+); ppy = 2,2'-bipyridine, 2,2'bipyridine-4,4'-dicarboxylate, o-phenanthroline, tetrahydro-4,4'-dialkyl-bis-oxazole) oxidize in organic or aqueous alkaline solution primary and secondary alcohols to aldehydes or ketones and are thereby reduced to the Rh(I) complexes Cp*Rh(ppy). The Rh(III) form can be regenerated by oxidants like pyruvate or oxygen, making the reaction quasi-catalytic. The reaction follows an autocatalytic pathway; hydrogen transfer from the alpha -CH2 group of an alcoholate complex [Cp*Rh(ppy)(OR)](+) to Cp*Rh(I)(ppy) is suggested to yield the Rh(III) intermediate Cp*Rh(ppy)H as the key and rate determining step. The knowledge of Rh(III)/Rh(I) redox potentials allows to estimate the thermodynamic driving force of the reaction which is not more than about 300 mV.

  DOI：

  10.1007/s007060070011

文献信息

• Fixation of Molecular Nitrogen Using Aliphatic Carboxylic Acid by Nitrogen Arc Plasma. Formation of Amino Acids
  作者：Michiaki Takasaki、Kaoru Harada

  DOI：10.1246/cl.1987.365

  日期：1987.2.5

  When argon-nitrogen plasma was blown into an aqueous solution containing aliphatic carboxylic acids, formation of several amino acids and amines was identified.

  当氩氮等离子体喷入含有脂肪族羧酸的水溶液中时，发现形成了几种氨基酸和胺。
• Oxidation reaction of amino acids in aqueous solution induced by argon arc plasma
  作者：Kaoru Harada、Michiaki Takasaki

  DOI：10.1016/s0040-4039(00)94021-8

  日期：1983.1

  It was found that Argon arc plasma induced a powerful and clean stepwise oxidation reaction in aqueous solution containing various amino acids without using any oxidizing agent.

  发现在不使用任何氧化剂的情况下，氩弧等离子体在包含多种氨基酸的水溶液中诱导了强大且清洁的逐步氧化反应。
• Under-flame Oxidation of Amines and Amino Acids in an Aqueous Solution
  作者：Shinya Nomoto、Akira Shimoyama、Susumu Shiraishi、Denzo Sahara

  DOI：10.1271/bbb.60.1851

  日期：1996.1

  Flames from town gas–oxygen, hydrogen–oxygen, and ethylene–oxygen mixtures, when blown against the surface of an aqueous solution of amines and amino acids, induced an oxidation reaction in the aqueous phase, while an acetylene–oxygen flame failed to oxidize the compounds in solution. The hydrogen flame caused direct hydroxylation of the aromatic rings of phenylglycine homologs. The isomeric ratio of o-, m-, and p-hydroxyphenyl-amino acids produced was in accordance with that obtained by using the reaction systems of Fe2+ −H2O2–EDTA and Fe2+–ascorbic acid–H2O2–EDTA, which are known to involve a hydroxyl radical as the agent for hydroxylating the aromatic rings. These results strongly suggest that the active species of flame-induced oxidation in an aqueous solution was the hydroxyl radical which was produced in the flames and extracted into the aqueous phase.

  城镇煤气-氧气、氢气-氧气和乙烯-氧气混合物的火焰吹向胺和氨基酸水溶液的表面时，会引起水相中的氧化反应，而乙炔-氧气火焰则不能氧化溶液中的化合物。氢焰直接导致苯甘氨酸同系物的芳香环发生羟基化反应。生成的邻羟基、间羟基和对羟基苯胺酸的异构体比例与使用 Fe2+ -H2O2-EDTA 和 Fe2+- 抗坏血酸-H2O2-EDTA 反应体系所得到的异构体比例一致，已知这两种反应体系都是以羟基自由基作为使芳香环羟基化的媒介。这些结果有力地表明，在水溶液中火焰诱导氧化的活性物种是在火焰中产生并被萃取到水相中的羟基自由基。
• Durgannavar, Amar K.; Patgar, Manjanath B.; Chimatadar, Shivamurti A., Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 2015, vol. 54A, # 9, p. 1085 - 1091
  作者：Durgannavar, Amar K.、Patgar, Manjanath B.、Chimatadar, Shivamurti A.

  DOI：——

  日期：——
• Oxidation of Alcohols by [Cp*Rh( ppy)(OH)]+
  作者：Ulrich Kölle、Holger Fränzl

  DOI：10.1007/s007060070011

  日期：2000.12.13

  Rh(III) polypyridine complexes ([Cp*Rh(ppy)(H2O)(2+); ppy = 2,2'-bipyridine, 2,2'bipyridine-4,4'-dicarboxylate, o-phenanthroline, tetrahydro-4,4'-dialkyl-bis-oxazole) oxidize in organic or aqueous alkaline solution primary and secondary alcohols to aldehydes or ketones and are thereby reduced to the Rh(I) complexes Cp*Rh(ppy). The Rh(III) form can be regenerated by oxidants like pyruvate or oxygen, making the reaction quasi-catalytic. The reaction follows an autocatalytic pathway; hydrogen transfer from the alpha -CH2 group of an alcoholate complex [Cp*Rh(ppy)(OR)](+) to Cp*Rh(I)(ppy) is suggested to yield the Rh(III) intermediate Cp*Rh(ppy)H as the key and rate determining step. The knowledge of Rh(III)/Rh(I) redox potentials allows to estimate the thermodynamic driving force of the reaction which is not more than about 300 mV.