N-甲氧基羰基-2-甲氧基-DL-甘氨酸甲酯 | 143995-55-5

• 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-甲氧基羰基-2-甲氧基-DL-甘氨酸甲酯
• 英文名称: 2--2-methoxyethanoate
• 英文别名: methyl 2-methoxy-2-(methoxycarbonylamino)acetate；methyl N-moc-α-methoxyglycinate；Methyl α-methoxy-N-(methoxycarbonyl)glycinate；Methyl-N-methoxycarbonyl-α-methoxyglycinat；Methoxy-methoxycarbonylamino-acetic acid methyl ester；Methyl methoxy[(methoxycarbonyl)amino]acetate
• CAS: 143995-55-5
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: NITAEFBYXPKQDN-UHFFFAOYSA-N

物化性质

• 沸点：
  285.6±30.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲氧基羰基-2-甲氧基-DL-甘氨酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 lithium diisopropyl amide 、 三氯化磷 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 23.0h， 生成 (3R,4S)-Methyl 4-(benzyloxy)-3-bromo-2-pentanoate
  参考文献：
  名称：

  Stereoselective bromination of dehydroamino acids with controllable retention or inversion of olefin configuration

  摘要：

  Dehydroamino acid esters react with brominating reagents to produce syn-a-bromo imines as the major products, which undergo tautomerization to mixtures of the diastereomeric (E)- and (Z)-beta-bromo-alpha,beta-dehydroamino acids upon treatment with base. Herein, we examine the characteristics of dehydroamino acid substrates 1 that affect both the diastereofacial selectivity of the bromination and the configuration of the resulting olefin product(s) 3. In these studies, we demonstrate E- and Z-diastereoselectivity for this reaction using kinetic and thermodynamic reaction conditions. Z-Vinyl bromides were shown to be the thermodynamically more stable products and were formed from the kinetic E-isomers by DABCO-induced isomerization. High levels of kinetic E-selectivity were obtained by treatment of the intermediate alpha-bromo imines with hindered amine bases such as 2,2,6,6-tetramethylpiperidine or sodium hexamethyldisilazide. The reaction conditions detailed herein allow for the stereodivergent preparation of both E- and Z-vinyl bromide products from either diastereomeric E- or Z-olefin starting material with useful levels of diastereoselectivity.

  DOI：

  10.1021/jo00068a047
• 作为产物：
  描述：

  甲醇 、 2-羟基-2-(甲氧基羰基氨基)乙酸 在 硫酸 作用下， 生成 N-甲氧基羰基-2-甲氧基-DL-甘氨酸甲酯
  参考文献：
  名称：

  N-取代的氮丙啶-2-羧酸酯的合成

  摘要：

  描述了通过使2-氯-N-碳烷氧基甘氨酸甲酯1与重氮甲烷反应来合成N-甲氧基羰基-和N-苄氧基羰基氮丙啶-2-羧酸2的甲酯的方法。氮丙啶易于转化为O-甲基丝氨酸5和S-甲基半胱氨酸6的衍生物。

  DOI：

  10.1016/0040-4020(77)80039-2

文献信息

• Lewis-acid-induced reactions of α-methoxyglycinamide derivatives with silyl enol ethers. Formation of 3-amino-2-pyrrolidinones and 3-amino-2-pyrrolinones
  作者：Eric C. Roos、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1002/recl.19921110705

  日期：——

  -methoxyacetamides were subjected to borontrifluoride-etherate-mediated reactions with one silyl ketene acetal and four silyl enol ethers. Reactions of primary and secondary amides did not lead to the desired CCbond formation. Reactions of the tertiary N,N-dimethylamide gave the expected γ-oxo-α-aminocarboxamides. The reaction of an N-methoxy-N-trimethylsilylcarboxamide with the ketene acetal also

  为了开发方便的合成γ-氧代-α-氨基羧酰胺的方法，将五种不同的α-（烷氧基羰基）氨基-α-甲氧基乙酰胺与三氟硼化硼酸乙酯介导的反应与一种甲硅烷基乙烯酮缩醛和四种甲硅烷基烯醇醚进行了反应。伯酰胺和仲酰胺的反应未导致所需的C C键形成。N，N-二甲基酰胺叔胺的反应给出了预期的γ-氧代-α-氨基羧酰胺。一个的反应Ñ甲氧基Ñ -trimethylsilylcarboxamide与乙烯酮缩二醇也正常进行。但是，后者酰胺与甲硅烷基烯醇醚的初始产物分别通过环化进一步反应，得到环状的N-甲氧基-N-酰基中间体。根据所使用的烯醇醚的结构特征，这亚胺中间遭受任一质子损失和异构化，得到保护的3-氨基-1-甲氧基δ 3 -吡咯啉-2-酮，或进行与该烯醇醚，得到的第二联接保护的3-氨基-1-甲氧基吡咯烷二-2-酮。
• [EN] COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSÉS UTILISABLES POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：SCHERING CORP

  公开号：WO2010054279A1

  公开（公告）日：2010-05-14

  This invention relates to compounds of the Formula (I): (Chemical formula should be inserted here as it appears on abstract in paper form) (I) or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, ADAMs, TACE, aggrecanase, TNF- or combinations thereof.

  本发明涉及式(I)的化合物：（化学式应按照纸质摘要中的形式插入在此处）（I）或其药用可接受的盐、溶剂合物或异构体，可用于治疗由MMPs、ADAMs、TACE、聚集素酶、TNF-或其组合介导的疾病或症状。
• A photocaged, cyclopropene-containing analog of the amino acid neurotransmitter glutamate
  作者：Pratik Kumar、David Shukhman、Scott T. Laughlin

  DOI：10.1016/j.tetlet.2016.10.106

  日期：2016.12

  that control neuron excitation and inhibition, are not among the systems that have been studied using biorthogonal chemistry. Here we describe the synthesis of cyclopropene-containing analogs of the excitatory amino acid neurotransmitter glutamate starting from a Garner's aldehyde-derived alkyne. The deprotected cyclopropene glutamate was stable in solution but decomposed upon concentration. Appending

  取代环丙烯作为紧凑的双正交附属物，能够分析复杂系统中的生物分子。神经递质是控制神经元兴奋和抑制的一组化学多样化的生物分子，不属于使用双正交化学研究的系统之列。在这里，我们描述了从加纳醛衍生的炔烃开始合成兴奋性氨基酸神经递质谷氨酸的含环丙烯类似物。脱保护的环丙烯谷氨酸盐在溶液中稳定，但在浓缩时分解。附加光可裂解基团提高了环丙烯的稳定性，同时限制了神经递质。该策略有可能允许将环丙烯修饰的谷氨酸用作体内神经递质谷氨酸的生物正交探针，并具有时空精度。
• Synthesis of a Naturally Occurring Diene-Containing Amino Acid and Its Glutamyl Dipeptide viaN-Acyliminium Ion Chemistry
  作者：Martin Berkheij、Jan Dijkink、Olivier R. P. David、Theo Sonke、Denis R. IJzendoorn、Richard H. Blaauw、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra

  DOI：10.1002/ejoc.200701016

  日期：2008.2

  The syntheses of the naturally occurring unusual unsaturated amino acid (S)-2-amino-3-methylene-4-pentenoic acid and the corresponding gamma-glutamyl dipeptide are described. Key steps are an N-acyliminium ion addition using allenyhnethylsilane as nucleophile and an enzymatic resolution mediated by the L-aminopeptidase from Pseudomonas putida.

  描述了天然存在的罕见不饱和氨基酸 (S)-2-amino-3-methylene-4-pentenoic 酸和相应的 γ-谷氨酰二肽的合成。关键步骤是使用丙二烯基乙基硅烷作为亲核试剂的 N-acyliminium 离子加成和由来自恶臭假单胞菌的 L-氨基肽酶介导的酶促拆分。
• Synthesis of γ,δ,-unsaturated α-amino acids from allylsilanes and glycidyl cation equivalents
  作者：Hendrik H. Mooiweer、Henk Hiemstra、W.Nico Speckamp

  DOI：10.1016/s0040-4020(01)89098-0

  日期：——

  The synthesis of a series of γ,δ-unsaturated N-protected α-amino acid methyl esters from the coupling of different allylsilanes and glycidyl cation equivalents 6 and 7 is described. Reactions with methoxyglycine derivative 6 are induced with BF3·OEt2; in the case of chloroglycine derivative 7 SnCl4 is used as Lewis acid. Reactions are fully regioselective, but show low stereoselectivity. The conversion

  描述了由不同的烯丙基硅烷和缩水甘油基阳离子当量6和7的偶联合成一系列的γ，δ-不饱和的N-保护的α-氨基酸甲基酯。BF 3 ·OEt 2诱导与甲氧基甘氨酸衍生物6的反应。在氯甘氨酸衍生物7的情况下，将SnCl 4用作路易斯酸。反应是完全区域选择性的，但显示出低的立体选择性。在两种情况下描述了反应产物向未保护的α-氨基酸的转化。