(4-甲基-3,5-二氧代-1-哌嗪基)乙酸 | 173681-12-4

• 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: (4-甲基-3,5-二氧代-1-哌嗪基)乙酸
• 中文别名: 1H-吡咯-2-胺,1-乙基-(9CI)
• 英文名称: 1-methyl-2,6-dioxopiperazineacetic acid
• 英文别名: (4-Methyl-3,5-dioxopiperazin-1-YL)acetic acid；2-(4-methyl-3,5-dioxopiperazin-1-yl)acetic acid
• CAS: 173681-12-4
• 化学式: C₇H₁₀N₂O₄
• 分子量: 186.167
• InChiKey: STZUPKAXFHAYFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基甲酰胺 、 次氮基三乙酸 以28%的产率得到(4-甲基-3,5-二氧代-1-哌嗪基)乙酸
  参考文献：
  名称：

  Nitrilotriacetamide: Synthesis in Concentrated Sulfuric Acid and Stability in Water

  摘要：

  Acid hydrolysis of N(CH2CN)(3) leads either nitrilotriacetamide, 1, and/or 3,5-dioxopiperazineacetamide, 4, in quantitative yield. 1 slowly and cleanly converts to 3,5-dioxopiperazineacetic acid, 5, in water, although ammonium salts prevent this reaction.

  DOI：

  10.1080/00397919508011491

文献信息

• [EN] METHOD FOR THE SYNTHESIS OF N-PHOSPHONOMETHYLIMINODIACETIC ACID<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'ACIDE N-PHOSPHONOMÉTHYLIMINODIACÉTIQUE
  申请人：STRAITMARK HOLDING AG

  公开号：WO2014012986A1

  公开（公告）日：2014-01-23

  The present invention is related to a method for the synthesis of N- phosphonoalkyliminodiacetic acid or derivatives thereof comprising the steps of: a) forming a reaction mixture comprising an acid catalyst, a compound having the general formula R1 -CH2-NX-CH2-R2 and a compound having one or more P-O-P anhydride moieties, to form a compound having the general formula R1 - CH2-N-CH2(P03H2)-CH2-R2, its dehydrated forms or their derivatives, wherein - the compound of the formula R1 -CH2-NX-CH2-R2 is characterized in that: - X is -CH2-OH or -CH2-COOH; - R1 and R2 are independently selected from the group consisting of nitrile, C1 -C4 alkyl carboxylate, or are both carbonyl groups linked by means of a hydrogen substituted nitrogen atom or a C1 -C4- akyl substituted nitrogen atom; - the P-O-P anhydride comprising compound is characterized in that said anhydride moieties comprise one P atom at the oxidation state (+I II ) and one P atom at the oxidation state (+I II ) or (+V); and b) hydrolysing the reaction mixture to form N- phosphonomethyliminodiacetic acid or one of its derivatives.

  本发明涉及一种合成N-磷酸基烷基亚乙酸或其衍生物的方法，包括以下步骤：a）形成反应混合物，包括酸催化剂、具有一般式R1-CH2-NX-CH2-R2的化合物和具有一个或多个P-O-P酐基团的化合物，以形成一般式R1-CH2-N-CH2(P03H2)-CH2-R2的化合物、其脱水形式或其衍生物，其中-具有一般式R1-CH2-NX-CH2-R2的化合物的特点是：-X为-CH2-OH或-CH2-COOH；-R1和R2独立地选自由氰基、C1-C4烷基羧酸酯组成的群，或通过氢代氮原子或C1-C4烷基取代的氮原子连接的两个羰基基团；-包含P-O-P酐基团的化合物的特点是，所述酐基团包括一个氧化态为(+I II)的P原子和一个氧化态为(+I II)或(+V)的P原子；b）水解反应混合物以形成N-磷酸基甲基亚乙酸或其衍生物之一。
• METHOD FOR THE SYNTHESIS OF N-PHOSPHONOMETHYLIMINODIACETIC ACID
  申请人：STRAITMARK HOLDING AG

  公开号：US20150166584A1

  公开（公告）日：2015-06-18

  A method for synthesis of N-phosphonoalkyliminodiacetic acid or derivatives thereof by: 1) forming a reaction mixture having an acid catalyst, a compound having the general formula R 1 —CH 2 —NX—CH 2 —R 2 and a compound having one or more P—O—P anhydride moieties, to form a compound having the general formula R 1 —CH 2 —N—CH 2 (PO 3 H 2 )—CH 2 —R 2 , its dehydrated forms or their derivatives, wherein the compound of the formula R 1 —CH 2 —NX—CH 2 —R 2 is characterized in that: X is —CH 2 —OH or —CH 2 —COOH; and R 1 and R 2 are independently selected from the group consisting of nitrile, C 1 -C 4 alkyl carboxylate, or are both carbonyl groups linked by a hydrogen substituted nitrogen atom or a C 1 -C 4 -akyl substituted nitrogen atom; the P—O—P anhydride compound is characterized in that the anhydride moieties have one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V); and 2) hydrolysing the reaction mixture to form N-phosphonomethyliminodiacetic acid or one of its derivatives.

  一种合成N-磷酸脂肪基亚乙酸或其衍生物的方法，包括以下步骤：1）形成反应混合物，其中包括酸性催化剂、具有一般式R1-CH2-NX-CH2-R2的化合物和具有一个或多个P-O-P酸酐基团的化合物，以形成具有一般式R1-CH2-N-CH2(PO3H2)-CH2-R2的化合物、其脱水形式或其衍生物，其中一般式R1-CH2-NX-CH2-R2的化合物的特点在于：X为-CH2-OH或-CH2-COOH；R1和R2分别选自氰基、C1-C4烷基羧酸酯的群或由氢代替的氮原子或C1-C4烷基取代的氮原子连接的两个羰基基团；P-O-P酸酐化合物的特点在于酸酐基团具有一个P原子在氧化态(+III)，一个P原子在氧化态(+III)或(+V)；2）水解反应混合物，以形成N-磷酸甲基亚乙酸或其衍生物之一。
• Method for the synthesis of N-phosphonomethyliminodiacetic acid
  申请人：MONSANTO TECHNOLOGY LLC

  公开号：US10364262B2

  公开（公告）日：2019-07-30

  A method for synthesis of N-phosphonoalkyliminodiacetic acid or derivatives thereof by forming a reaction mixture having an acid catalyst, a compound of the following general formula R1—CH2—NX—CH2—R2 and a compound having one or more P—O—P anhydride moieties to form a compound having a formula R1—CH2—N(—CH2PO3R32)(—CH2—R2) wherein in R1—CH2—NX—CH2—R2: X is —CH2—OH or —CH2—COOH; R1 and R2 are independently selected from the group consisting of nitrile, C1-C4 alkyl carboxylate, and carboxylic acid for when X is —CH2—OH, or R1 and R2 are both carbonyl groups linked by a hydrogen substituted nitrogen atom or a C1-C4-alkyl substituted nitrogen atom; and R3 is H, an alkyl group, or an aryl group; the anhydride moieties in the P—O—P anhydride compound have one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V); and 2) hydrolyzing the mixture to form N-phosphonomethyliminodiacetic acid or one of its derivatives.

  一种合成N-膦酰基亚烷基二醋酸或其衍生物的方法，通过形成一种反应混合物，该混合物具有酸催化剂、下通式R1-CH2-NX-CH2-R2的化合物和具有一个或多个P-O-P酸酐分子的化合物，以形成具有式R1-CH2-N(-CH2PO3R32)(-CH2-R2)的化合物，其中在R1-CH2-NX-CH2-R2中，X是-CH2-OH或-CH2-COOH；R1和R2独立地选自由腈、C1-C4烷基羧酸盐和羧酸组成的组：X为-CH2-OH或-CH2-COOH；当X为-CH2-OH时，R1和R2独立地选自腈、C1-C4烷基羧酸酯和羧酸组成的组，或者R1和R2都是由氢取代的氮原子或C1-C4烷基取代的氮原子连接的羰基；和 R3 是 H、烷基或芳基；P-O-P 酸酐化合物中的酸酐分子有一个 P 原子处于氧化态 (+III)，一个 P 原子处于氧化态 (+III) 或 (+V)；和 2）水解混合物以形成 N-膦酰甲基亚氨基二乙酸或其衍生物之一。
• Nitrilotriacetamide: Synthesis in Concentrated Sulfuric Acid and Stability in Water
  作者：Douglas A. Smiths、Steven Sucheck、Susan Cramer、David Baker

  DOI：10.1080/00397919508011491

  日期：1995.12

  Acid hydrolysis of N(CH2CN)(3) leads either nitrilotriacetamide, 1, and/or 3,5-dioxopiperazineacetamide, 4, in quantitative yield. 1 slowly and cleanly converts to 3,5-dioxopiperazineacetic acid, 5, in water, although ammonium salts prevent this reaction.