乙酰氨基丙二酸 | 55327-87-2

• 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: 乙酰氨基丙二酸
• 英文名称: 2-acetamidomalonic acid
• 英文别名: acetamidomalonic acid；acetamidomalonate；acetylamino-malonic acid；Acetylamino-malonsaeure；Acetamino-malonsaeure；Acetaminomalonsaeure；2-acetamidopropanedioic acid
• CAS: 55327-87-2
• 化学式: C₅H₇NO₅
• 分子量: 161.114
• InChiKey: JFTHBDBUVHRREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  ethenyl-ethoxy-oxophosphanium 、 乙酰氨基丙二酸 在 盐酸 作用下， 生成 3-amino-3-carboxypropylphosphonous acid
  参考文献：
  名称：

  Maier, Ludwig, Phosphorus and Sulfur and the Related Elements, 1983, vol. 14, p. 295 - 322

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰氨基丙二酸二甲酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 乙酰氨基丙二酸
  参考文献：
  名称：

  Synthese aliphatischer α-Amino-β-hydroxy-carbonsäuren durch Aldolreaktion mit Acetaminomalonsäure und deren Monoester

  摘要：

  DOI：

  10.1515/bchm2.1960.318.1.66

文献信息

• Convenient Method for Reduction of C-N Double Bonds in Oximes, Imines, and Hydrazones Using Sodium Borohydride–Raney Ni System
  作者：Yihua Yang、Shouxin Liu、Junzhang Li、Xia Tian、Xiaoli Zhen、Jianrong Han

  DOI：10.1080/00397911.2011.562063

  日期：2012.9

  Abstract A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. GRAPHICAL

  摘要 开发了一种在 Raney Ni 催化下用硼氢化钠还原肟、亚胺和腙中 CN 双键的实用方法。反应在碱性水溶液中进行，经过简单的程序，以中等收率得到所需产物。该方法可用于合成更简单的脂肪族或芳香族胺及其类似物。图形概要
• Synthesis and decarboxylation of Δ²-cephem-4,4-dicarboxylic acids
  作者：Saul Wolfe、Stephen Ro、Chan-Kyung Kim、Zheng Shi

  DOI：10.1139/v01-100

  日期：2001.8.1

  Penicillin V was converted in 14 steps into Δ²-cephems having hydrogen at C-3, hydrogen or ethyl at C-2, and two methoxycarbonyl, two benzyloxycarbonyl, or one methoxycarbonyl and one benzyloxycarbonyl substituent at C-4. Deprotection of these Δ²-cephem-4,4-dicarboxylic acid esters by alkaline hydrolysis (in the case of methyl esters) or hydrogenolysis (in the case of benzyl esters) led in all cases to rapid decarboxylation of the Δ²-cephem-4,4-dicarboxylic acid or Δ²-cephem-4,4-dicarboxylic acid monoester. With hydrogen at C-2, hydrolysis of the dimethyl ester with 1 equiv of base produced a Δ²-cephem. With 2 equiv of base, and with all compounds having methyl at C-2, hydrolysis or hydrogenolysis afforded 4α-substituted-Δ²-cephems.

  In contrast, simpler benzyl or methyl acetamidomalonates could be deprotected without difficulty to afford stable malonic acids. Reasons for the differences in ease of decarboxylation were examined using semiempirical (AM1) and ab initio (3-21G) molecular orbital calculations. The decarboxylation barriers of unionized cephem or acetamido malonic acids were found to be high (35–40 kcal mol^–1). Although the monoanion of acetamidomalonic acid retained a high barrier, the epimeric monoanions of a Δ²-cephem malonic acid decarboxylated with barriers of only 2 kcal mol^–1.Key words: mercaptoazetidinone, bromomalonate esters, MO calculations, sulfoxides, hydrogenolysis.

  青霉素V经过14个步骤转化为具有C-3处氢、C-2处氢或乙基，以及C-4处两个甲氧羰基、两个苄氧羰基或一个甲氧羰基和一个苄氧羰基取代基的Δ2-头孢菌素。通过碱性水解（对甲酯类）或氢解（对苄酯类）去保护这些Δ2-头孢菌素-4,4-二羧酸酯，在所有情况下都导致Δ2-头孢菌素-4,4-二羧酸或Δ2-头孢菌素-4,4-二羧酸单酯的快速脱羧。C-2处为氢时，用1当量碱水解二甲酯酯类产生Δ2-头孢菌素。用2当量碱，并且所有化合物C-2处为甲基时，水解或氢解得到4α-取代的Δ2-头孢菌素。 相比之下，更简单的苄或甲基乙酰胺丙二酸酯可以轻松去保护以得到稳定的丙二酸。使用半经验（AM1）和从头算（3-21G）分子轨道计算研究了脱羧难易度差异的原因。发现未离子化的头孢菌素或乙酰胺丙二酸的脱羧能垒较高（35-40 kcal mol-1）。尽管乙酰胺丙二酸的单负离子保留了较高的能垒，但Δ2-头孢菌素丙二酸的异构单负离子脱羧能垒仅为2 kcal mol-1。关键词：巯基氮杂环丙酮酮，溴丙二酸酯，分子轨道计算，亚氧化物，氢解。
• Asymmetric Synthesis of Telcagepant, a CGRP Receptor Antagonist for the Treatment of Migraine
  作者：Feng Xu、Michael Zacuto、Naoki Yoshikawa、Richard Desmond、Scott Hoerrner、Tetsuji Itoh、Michel Journet、Guy R. Humphrey、Cameron Cowden、Neil Strotman、Paul Devine

  DOI：10.1021/jo101704b

  日期：2010.11.19

  A highly efficient, asymmetric synthesis of telcagepant (1), a CGRP receptor antagonist for the treatment of migraine, is described. This synthesis features the first application of iminium organocatalysis on an industrial scale. The key to the success of this organocatalytic transformation was the identification of a dual acid cocatalyst system, which allowed striking a balance of the reaction efficiency

  描述了一种高效，不对称合成的telcagepant（1）（一种用于治疗偏头痛的CGRP受体拮抗剂）。该合成的特征是在工业规模上首次应用亚胺基有机催化。该有机催化转化成功的关键是双酸助催化剂体系的鉴定，该体系可在反应效率和产物稳定性之间取得有效平衡。这样，通过亚胺鎓类，实际上在> 95％ee的一次操作中就建立了必要的C-6立体定向性。此外，我们争取到了前所未有的Doebner-Knoevenagel偶联，该偶联也通过亚胺基物种进行，以有效地构建具有所需功能的C3-C4键。为了准备telcagepant（1）以高品质发现了一种实用的新方案，可将在氢化条件下形成的脱氟杂质的形成抑制到<0.2％。通过t - BuCOCl促进的有效内酰胺化，然后进行动态差向异构化结晶，可以干净地分离出具有所需C3（R）和C6（S）构型的己内酰胺乙酰胺。仅分离三种中间体，这种经济高效的合成方法的总收率高达27％。这种
• Aminoketones. I. The Preparation of α-Aminoketones from Di-t-butyl Acetamidomalonate²
  作者：Anthony W. Schrecker、Mary M. Trail

  DOI：10.1021/ja01555a045

  日期：1958.11
• Novel potential neuroprotective agents with both iron chelating and amino acid-based derivatives targeting central nervous system neurons
  作者：Hailin Zheng、Moussa B.H. Youdim、Lev M. Weiner、Mati Fridkin

  DOI：10.1016/j.bcp.2005.09.003

  日期：2005.11

  Antioxidants and iron chelating molecules are known as neuroprotective agents in animal models of neurodegenerative disorders such as Alzheimer's disease (AD) and Parkinson's disease (PD). In this study, we designed and synthesized a novel bifunctional molecule (M10) with radical scavenging and iron chelating ability on an amino acid carrier likely to be a substrate for system L, thus targeting the compound to the central nervous system (CNS). M10 had a moderate iron affinity in HEPES buffer (pH 7.4) with log K-3 = 12.25 +/- 0.55 but exhibited highly inhibitory action against iron-induced lipid peroxidation, with an IC50 value (12 mu M) comparable to that of desferal (DFO). EPR studies indicated that M10 was a highly potent (center dot)0H scavenger with an IC50 of about 0.3 molar ratio of M10 to H2O2. In PC12 cell culture, M10 was at least as potent as the anti-Parkinson drug rasagiline in protecting against cell death induced by serum-deprivation and by 6-hydroxydopamine (6-OHDA). These results suggest that M10 deserves further investigation as a potential agent for the treatment of neurodegenerative disorders such as AD and PD. (c) 2005 Elsevier Inc. All rights reserved.