CAS: 4408-64-4; 2,2'-(Methylazanediyl)Diacetic Acid

该化合物是一种多用途的铬酸剂和合成中间体,在有机化学和协调化学中广泛使用,其主要优势包括能够形成稳定的金属离子复合体,使其在催化,金属固存方面具有价值,并成为浸泡物合成中的保护群体.甲基替代会提高其有机溶剂中的溶解性,促进其在多种反应条件下的使用.MIDA还被用于制备boronates,并用作交叉组合反应中的捆绑剂.它与各种功能团体的稳健稳定性和兼容性使得它成为需要精确控制金属协调或选择性反应的首选应用选择.

结构式图片

相似化合物

56074-20-5 3987-53-9 112918-82-8

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

glycolonitrile methylamine chloroacetic acid formaldehyddiethyl 2,2'-(methylimino)diacetate 1-methylpiperazine-3,5-dione (N-methylimino)diacetic acid anhydride 4]piperazine1-methyl[3,3,5,5-D4]piperazine

合成工艺路线路线简述

  • 合成目标产物 N-Methyliminodiacetic Acid 主要起始原料 Acetyleneboronic Acid Mida Ester, Acetynylboronic Acid Mida Ester, Ethyneboronic Acid Mida Ester
  • (文献来源)合成步骤主要原料 Acetyleneboronic Acid Mida Ester, Acetynylboronic Acid Mida Ester, Ethyneboronic Acid Mida Ester
Phenylboronic Acid Mida Ester 以 甲醇,水 作为反应溶剂,以38%的收率获得产物n-甲基亚氨二乙酸
参考文献:Syntheses Of (N-> B)Phenyl[n-Alkylaminodiacetate-O,O',N]Boranes
标题:Syntheses Of (N-> B)Phenyl[n-Alkylaminodiacetate-O,O',N]Boranes
摘要:The Syntheses Of (N-->B)Phenyl[n-Alkylaminodiacetate-O,O',N]Boranes (2 To 6) And Their Corresponding N-Alkylaminodiacetic Acids (7 To 10) Are Reported. All Compounds (Except 6) Were Characterized By H-1,B-11 (For Boron Heterocycles),C-13 NMR,Infrared Spectroscopy And Mass Spectrometry. The H-1 NMR Spectrum Of Compound 3 Shows That It Is A Chiral Molecule,Its Structure Was Determined By Homonuclear Decoupling Experiments,H-1 NMR And Hetcor. The Study Of The Intramolecular N-->B Coordination By Dynamic NMR Afforded A Delta G Double Dagger Value Of 98.4 Kj Mol(-1) For Compound 3. Copyright (C) 1996 Elsevier Science Ltd
DOI:10.1016/0277-5387(96)00109-X

海关参考信息

专利信息


专利号:US-9388131-B2
优先权日:2011-04-27
标题:Automated synthesis of small molecules using chiral, non-racemic boronates
发明人:BURKE MARTIN D; LI JUNQI; GILLIS ERIC P
权利人:UNIV ILLINOIS
摘要:Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.

专利号:US-9862733-B2
优先权日:2010-07-23
标题 :Apparatus and methods for the automated synthesis of small molecules
发明人:BURKE MARTIN D; GILLIS ERIC P; BALLMER STEVEN G
权利人:BURKE MARTIN D; GILLIS ERIC P; BALLMER STEVEN G; UNIV ILLINOIS
摘要:Provided are methods for purifying N-methyliminodiacetic acid (MIDA) boronates from solution. Also provided are methods for deprotection of boronic acids from their MIDA ligands. The purification and deprotection methods can be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chemical compounds of interest. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated synthesis of small molecules using iterative cycles of deprotection, coupling, and purification in accordance with methods of the invention. Coupling and other reactions embraced by the invention include, without limitation, Suzuki-Miyaura coupling, oxidation, Swern oxidation, “Jones reagents†oxidation, reduction, Evans' aldol reaction, HWE olefination, Takai olefination, alcohol silylation, desilylation, p-methoxybenzylation, iodination, Negishi cross-coupling, Heck coupling, Miyaura borylation, Stille coupling, and Sonogashira copling.

专利号:US-10464958-B2
优先权日:2012-07-17
标题 :Method for the synthesis of alpha-aminoalkylenephosphonic acid
发明人:NOTTE PATRICK; COGELS SAMUEL; BURCK SEBASTIAN
权利人:MONSANTO TECHNOLOGY LLC
摘要:The present invention is related to a new method for the synthesis of alpha-aminoalkylenephosphonic acid or its phosphonate esters comprising the steps of forming a reaction mixture by mixing a P—O—P anhydride moiety comprising compound, having one P-atom at the oxidation state (+III) and the other P-atom at the oxidation state (+III) or (+V), an aminoalkanecarboxylic acid and an acid catalyst, wherein said reaction mixture comprises an equivalent ratio of alpha-aminoalkylene carboxylic acid to P—O—P anhydride moieties of at least 0.2, and recovering the resulting alpha-aminoalkylene phosphonic acid compound or an ester thereof from the reaction mixture.

专利号:US-6608196-B2
优先权日:2001-05-03
标题 :Process for solid supported synthesis of pyruvate-derived compounds
发明人:WANG BING; JANAGANI SATYANARAYANA; CALLAWAY WYETH B; SESSLER JONATHAN L
权利人:GALILEO PHARMACEUTICALS INC
摘要:Provided are processes for synthesizing structurally diverse pyruvate-derived compounds using a parallel approach on a solid phase support. Examples of such a solid phase support include resins which have also been used in solid phase peptide synthesis.

专利号:US-6118022-A
优先权日:1998-09-08
标 题 :Synthesis of phosphonomethyliminodiacetic acid with reduced effluent
发明人:CULLEN BARRY A
权利人:HAMPSHIRE CHEMICAL CORP
摘要:A process for the preparation of phosphonomethylglycine in high yields is disclosed. In accordance with the process of the present invention, alkali metal IDA, such as disodium IDA, is reacted with a strong mineral acid, such as HCl, to convert the salt of IDA to IDA. The IDA is then converted to soluble IDA phosphite salt by the addition of phosphorous acid, and the alkali metal salt of the strong acid is precipitated. The phosphite salt of IDA is phosphonomethylated, such as by the addition of PCl3 and formaldehyde. Optionally, phosphorous trichloride can be hydrolyzed to provide the phosphorous acid source for phosphonomethylation of the phosphite salt.

专利号:US-10844081-B2
优先权日:2015-08-07
标题 :Protected organoboronic acids with tunable reactivity, and methods of use thereof
发明人:BURKE MARTIN D; SCHMIDT MICHAEL; MOREHOUSE GREG; PIPAL ROBERT W
权利人:UNIV ILLINOIS
摘要:Disclosed are a range of protected organoboronic acid reagents useful in the modular assembly of complex organic compounds. The reactivities of the protected organoboronic acid reagents may be varied predictably by changes to the number and identities of their substituents. Also disclosed are methods of using the protected organoboronic acid reagents in the synthesis of organic compounds.
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主要参考文献

[参考文献]: B Siegmund, Et Al. Determination Of Meso-Alanopine And D-Strombine By High Pressure Liquid Chromatography In Extracts From Marine Invertebrates. Hoppe Seylers Z Physiol Chem. 1983 Jul;364(7):807-12.
[参考文献]: Christian Starkenmann, Et Al. Taste Contribution Of (R)-Strombine To Dried Scallop. J Agric Food Chem. 2009 Sep 9;57(17):7938-43.
[参考文献]: G Meinardus-Hager, Et Al. The Pyruvate Branchpoint In The Anaerobic Energy Metabolism Of The Jumping Cockle Cardium Tuberculatum L.: D-Lactate Formation During Environmental Anaerobiosis Versus Octopine Formation During Exercise. Exp Biol. 1986;45(2):91-110.
[参考文献]: J H Fields, Et Al. Alanopine And Strombine Are Novel Imino Acids Produced By A Dehydrogenase Found In The Adductor Muscle Of The Oyster, Crassostrea Gigas. Arch Biochem Biophys. 1980 Apr 15;201(1):110-4.
[参考文献]: K B Storey, Et Al. Gas-Liquid Chromatography And Enzymatic Determination Of Alanopine And Strombine In Tissues Of Marine Invertebrates. Anal Biochem. 1982 Sep 1;125(1):50-8.

合成参考文献


摘要:Trofimova, A.; Sirvinskas, M.; Yudin, A. K., Science of Synthesis Knowledge Updates, (2021) 2, 59.
摘要:Suginome, M.; Ohmura, T., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2012) 1, 192.
摘要:Zhou, M.; Qin, T., Science of Synthesis, (2020) , 505.
摘要:Zhang, F.-L.; Wang, Y.-F., Science of Synthesis, (2021) , 415.
摘要:Fagnoni, M.; Ravelli, D.; Protti, S., Science of Synthesis, (2020) , 347.
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