N-乙酰基草铵膦 | 73634-73-8

• 物质功能分类: 化学农药原药 - 除草剂
• 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: N-乙酰基草铵膦
• 英文名称: 2-acetylamino-4-(hydroxy(methyl)phosphinyl)butanoic acid
• 英文别名: N-acetylglufosinate；N-acetylphosphinothricin；2-acetamido-4-[hydroxy(methyl)phosphoryl]butanoic acid
• CAS: 73634-73-8
• 化学式: C₇H₁₄NO₅P
• 分子量: 223.166
• InChiKey: VZVQOWUYAAWBCP-UHFFFAOYSA-N

物化性质

• 沸点：
  666.1±50.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

制备方法与用途

简介

草铵膦-N-乙酰是一种有机磷类除草剂，具有低毒、高效、非选择性等特点。随着百草枯在全球范围内的逐渐禁用，草铵膦-N-乙酰的抗药性增强以及抗草铵膦转基因作物的广泛种植，目前这种除草剂已成为炙手可热的选择。

合成方法

采用 (3- 乙酰氧基 -3- 氰基 ) 丙基甲基次膦酸异丁酯（自制）作为初始原料，经过氨化得到 (3- 氨基 -3- 氰基 ) 丙基甲基次膦酸异丁酯，再通过酸解和提纯制得草铵膦原药。其合成反应式如下图所示：

反应信息

• 作为反应物：
  描述：

  N-乙酰基草铵膦 在 盐酸 、 甲烷 作用下， 反应 16.0h， 生成 L-glufosinate hydrochloride 、 D-phosphinothricin hydrochloride
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of phosphinothricin via asymmetric hydrogenation of .alpha.-acylamido acrylates

  摘要：

  Both enantiomers of phosphinothricin (1), a naturally occuring amino acid that contains the unique methylphosphinate moiety, were prepared by asymmetric hydrogenation of alpha-acylamido acrylate precursors 7. L-1 and peptides containing L-1 are inhibitors of the enzyme glutamine synthetase (GS). Inhibition of GS is responsible for the antibiotical and herbicidal properties of these compounds. Synthesis of substrates 7 and parameters influencing the enantioselectivity are discussed. Substrate concentration and solvent polarity appear to have the most marked effects on enantiomeric excesses for a given catalyst system. Enantiomeric excesses reach 91 % for hydrogenations with (R,R)-NORPHOS- and (S,S)-CHIRAPHOS-derived catalysts.

  DOI：

  10.1021/jo00005a024
• 作为产物：
  描述：

  草胺膦 、 乙酸酐 生成 N-乙酰基草铵膦
  参考文献：
  名称：

  ARAYA, SYUDZO;TAKIGAVA, SINITIRO;SUDZUKI, FUMIO

  摘要：

  DOI：

文献信息

• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINOPHOSPHINYLBUTANOIC ACIDS
  申请人：Minowa Nobuto

  公开号：US20090221851A1

  公开（公告）日：2009-09-03

  The present invention is a process for producing optically active aminophosphinylbutanoic acids represented by the formula (2) (in the formula (2), R 1 represents an alkyl group having 1 to 4 carbon atom(s), R 2 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), R 3 represents an alkyl group having 1 to 4 carbon atom(s), an alkoxy group having 1 to 4 carbon atom(s), an aryl group, an aryloxy group, or a benzyloxy group, and R 4 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s); and * represents an asymmetric carbon atom), wherein a compound represented by the formula (1) (in the formula (1), R 1 represents an alkyl group having 1 to 4 carbon atom(s), R 2 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), R 3 represents an alkyl group having 1 to 4 carbon atom(s), an alkoxy group having 1 to 4 carbon atom(s), an aryl group, an aryloxy group, or a benzyloxy group, and R 4 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s)) is asymmetrically hydrogenated in the presence of a ruthenium-optically active phosphine complex. With the process for the production, a compound useful in a herbicide such as L-AHPB can be produced with good efficiency and high asymmetric yield.

  本发明涉及一种制备光学活性氨基膦基丁酸的方法，其化学式为（2）（在化学式（2）中，R1代表具有1至4个碳原子的烷基，R2代表氢原子或具有1至4个碳原子的烷基，R3代表具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、芳基、芳氧基或苄氧基，R4代表氢原子或具有1至4个碳原子的烷基；*代表不对称碳原子），其中在钌-光学活性膦配合物的存在下，化学式（1）所表示的化合物（在化学式（1）中，R1代表具有1至4个碳原子的烷基，R2代表氢原子或具有1至4个碳原子的烷基，R3代表具有1至4个碳原子的烷基、具有1至4个碳原子的烷氧基、芳基、芳氧基或苄氧基，R4代表氢原子或具有1至4个碳原子的烷基）进行不对称氢化。通过该制备方法，可以高效率、高对映选择性地制备出一种在除草剂中有用的化合物，如L-AHPB。
• Process for producing optically active compounds
  申请人：NISSAN CHEMICAL INDUSTRIES, LIMITED

  公开号：EP0358428A2

  公开（公告）日：1990-03-14

  A process for producing an L-amino acid of formula (I): wherein R is -CH₂CO₂H, -CH₂CONH₂, -CO₂H or in which R¹ is a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a halogen-substituted alkyl group having 1 to 10 carbon atoms, which process comprises carrying out an optical resolution of an N-substituted carbonyl-D,L-amino acid of formula (II): wherein R is as defined above and R² is an alkanoyl group having 1 to 5 carbon atoms, a benzoyl group, a halogen-­substituted alkanoyl group having 1 to 5 carbon atoms or a halogen-substituted benzoyl group, or a salt thereof, or a mixture thereof, with cells of a microorganism, a microorganism fermentation broth, a treated microorganism fermentation broth, or a mixture thereof, said microorganism being selected from the bacteria of the genera Serratia, Staphylococcus, Bacillus, Flavobacterium Achromobacter and Alcaligenes and actinomycetes of the genera Actinoplanes, Streptosporangium and Sebekia.

  一种生产式(I)的 L-氨基酸的工艺： 其中 R 是-CH₂CO₂H、-CH₂CONH₂、-CO₂H 或 其中 R¹ 是氢原子、1 至 10 个碳原子的烷基或 1 至 10 个碳原子的卤代烷基、 该工艺包括对式（II）的 N-取代羰基-D,L-氨基酸进行光学解析： 其中 R 如上定义，R² 是具有 1 至 5 个碳原子的烷酰基、苯甲酰基、具有 1 至 5 个碳原子的卤代烷酰基或卤代苯甲酰基，或其盐，或其混合物、 与微生物细胞、微生物发酵液、经处理的微生物发酵液或它们的混合物一起，所述微生物选自沙雷氏菌属、葡萄球菌属、芽孢杆菌属、黄杆菌属、Achromobacter 属和 Alcaligenes 属的细菌以及放线菌属、链孢属和 Sebekia 属的放线菌。
• Enzymatic large-scale synthesis of mucin glyconjugates, and immunogenic applications thereof
  申请人：INSTITUT PASTEUR

  公开号：EP1808442A1

  公开（公告）日：2007-07-18

  The present invention relates to mucin glycoconjugates, and to a process of producing mucin glycoconjugates. It relates to the biological, pharmaceutical and medical applications thereof. The invention notably provides mucin glycoconjugates which do not require a protein carrier, such as KHL, to induce an immune response (anti-Tn IgG).

  本发明涉及粘蛋白糖苷轭合物，以及生产粘蛋白糖苷轭合物的工艺。 本发明还涉及其在生物、制药和医学方面的应用。本发明特别提供了不需要蛋白质载体（如 KHL）来诱导免疫反应（抗 Tn IgG）的粘蛋白糖结合物。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINOPHOSPHINYLBUTANOIC ACID
  申请人：Meiji Seika Kaisha Ltd.

  公开号：EP2060578A1

  公开（公告）日：2009-05-20

  The present invention is a process for producing optically active aminophosphinylbutanoic acids represented by the formula (2) (in the formula (2), R1 represents an alkyl group having 1 to 4 carbon atom(s), R2 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), R3 represents an alkyl group having 1 to 4 carbon atom(s), an alkoxy group having 1 to 4 carbon atom(s), an aryl group, an aryloxy group, or a benzyloxy group, and R4 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s); and * represents an asymmetric carbon atom), wherein a compound represented by the formula (1) (in the formula (1), R1 represents an alkyl group having 1 to 4 carbon atom(s), R2 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s), R3 represents an alkyl group having 1 to 4 carbon atom(s), an alkoxy group having 1 to 4 carbon atom(s), an aryl group, an aryloxy group, or a benzyloxy group, and R4 represents hydrogen atom or an alkyl group having 1 to 4 carbon atom(s)) is asymmetrically hydrogenated in the presence of a ruthenium-optically active phosphine complex. With the process for the production, a compound useful in a herbicide such as L-AHPB can be produced with good efficiency and high asymmetric yield.

  本发明是一种生产由式（2）表示的光学活性氨基膦酰丁酸的工艺 (在式(2)中，R1 代表具有 1 至 4 个碳原子的烷基，R2 代表氢原子或具有 1 至 4 个碳原子的烷基，R3 代表具有 1 至 4 个碳原子的烷基、具有 1 至 4 个碳原子的烷氧基、芳基、芳氧基或苄氧基，R4 代表氢原子或具有 1 至 4 个碳原子的烷基；和 * 代表不对称碳原子)，其中式(1)代表的化合物 (在式(1)中，R1 代表具有 1 至 4 个碳原子的烷基，R2 代表氢原子或具有 1 至 4 个碳原子的烷基，R3 代表具有 1 至 4 个碳原子的烷基、具有 1 至 4 个碳原子的烷氧基、芳基、芳氧基或苄氧基，R4 代表氢原子或具有 1 至 4 个碳原子的烷基) 在钌-光活性膦络合物存在下进行不对称氢化。通过该生产工艺，可以高效、高产地生产出用于除草剂（如 L-AHPB）的化合物。
• METHOD FOR DETECTING PESTICIDES IN FOOD PRODUCTS
  申请人：NofaLab B.V.

  公开号：EP3466510A1

  公开（公告）日：2019-04-10

  The present invention relates to a method for the detection of pesticides in food products. More particularly, the present invention relates to the detection of pesticides in food products by means of liquid chromatography and wherein the method comprises the use of an extraction liquid comprising a mixture of water (H2O), methanol (CH3OH) and formic acid (CH2O2), and an a-polar solvent. Furthermore, the present invention relates to the method wherein an additional purification step is carried out by means of solid phase extraction under vacuum.

  本发明涉及一种检测食品中农药的方法。更具体地说，本发明涉及通过液相色谱法检测食品中农药的方法，其中该方法包括使用由水（H2O）、甲醇（CH3OH）和甲酸（C 2）的混合物以及一种极性溶剂组成的萃取液。此外，本发明还涉及在真空条件下通过固相萃取进行额外纯化步骤的方法。