N-(2-(3,4-二甲氧基苯基)乙基)甘氨酸乙酯 | 56014-42-7

• 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-(2-(3,4-二甲氧基苯基)乙基)甘氨酸乙酯
• 英文名称: N-(2-(3,4-dimethoxyphenyl)ethyl)glycine ethyl ester
• 英文别名: N-(3,4-dimethoxyphenethyl)glycine ethyl ester；N-(3,4-dimethoxy-phenethyl)-glycine ethyl ester；N-(3,4-Dimethoxy-phenaethyl)-glycin-aethylester；Ethyl 2-[2-(3,4-dimethoxyphenyl)ethylamino]acetate
• CAS: 56014-42-7
• 化学式: C₁₄H₂₁NO₄
• mdl: MFCD00666341
• 分子量: 267.325
• InChiKey: VMTWPORWTIGSTI-UHFFFAOYSA-N

物化性质

• 沸点：
  160-161 °C(Press: 1.6 Torr)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(3,4-二甲氧基苯基)乙基)甘氨酸乙酯 在 盐酸 作用下， 生成 N-(3,4-二甲氧基苯乙基)-N-(甲苯-4-磺酰基)-甘氨酸
  参考文献：
  名称：

  Merchant, Journal Of Scientific and Industrial Research, 1957, vol. 16B, p. 512

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醇 、 N-(3,4-dimethoxy-phenethyl)-glycine nitrile 在 盐酸 作用下， 生成 N-(2-(3,4-二甲氧基苯基)乙基)甘氨酸乙酯
  参考文献：
  名称：

  Sugasawa; Mizukami, Chemical and pharmaceutical bulletin, 1958, vol. 6, p. 359,362

  摘要：

  DOI：

文献信息

• Domino Bischler-Napieralski - Michael Reaction and Oxidation - New Route to Coumarin-Pyrrole-Isoquinoline Fused Pentacycles
  作者：Ketan S. Mandrekar、Hari K. Kadam、Santosh G. Tilve

  DOI：10.1002/ejoc.201801244

  日期：2018.12.19

  The pentacyclic lamellarin core divides into four units, which can be connected through N‐alkylation, EDC‐coupling, and domino Bischler–Napieralski – Michael – Oxidation reaction sequences. This concise synthesis of lamellarin scaffolds makes it unique among other routes and highlights its importance in the wide field of lamellarin chemistry.

  五环lamellarin核心分为四个单元，可以通过N烷基化，EDC偶联和多米诺骨牌Bischler–Napieralski – Michael–氧化反应序列进行连接。层状蛋白支架的这种简洁的合成使其在其他途径中独树一帜，并突出了其在层状蛋白化学广泛领域中的重要性。
• Intramolecular Friedel−Crafts-Type Reactions Involving <i>N</i>-Acyliminium Ions Derived from Glycine Templates
  作者：Juan Domingo Sánchez、María Teresa Ramos、Carmen Avendaño

  DOI：10.1021/jo010166y

  日期：2001.8.1

  Enantiomerically pure 4-substituted 2-aralkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones (1b-m) in which the alkyl chain is (CH(2))(n), n = 1-3, behave as glycine templates giving by treatment with [hydroxy(tosyloxy)iodo]benzene in ethyl acetate cis-1-tosyloxy derivatives. When these compounds contain electron-rich aryl substituents with n = 2, they spontaneously cyclize through intramolecular

  对映体纯的4-取代的2-芳烷基-2,4-二氢-1H-吡嗪并[2,1-b]喹唑啉-3,6-二酮（1b-m），其中烷基链为（CH（2））（ n），n = 1-3，表现为甘氨酸模板，通过在乙酸乙酯的cis-1-tosyloxy衍生物中用[羟基（tosyloxy）碘]苯处理得到。当这些化合物包含n = 2的富电子芳基取代基时，它们通过分子内Friedel-Crafts型非对映选择性反应自发环化，生成五环或六环化合物。否则，它们通过溶剂分解得到顺式-1-烷氧基衍生物，如果n = 2、3，则可以在第二步中在酸中环化。所有这些反应必须通过类似于S（N）1机理的N-酰氨基发生。 。1-烷氧基-2-芳基甲基衍生物不愿环化，使反式-1-羟基化合物成为唯一的分离反应产物。
• The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine alkaloids lamellarin G trimethyl ether and ningalin B
  作者：John T. Gupton、Benjamin C. Giglio、James E. Eaton、Elizabeth A. Rieck、Kristin L. Smith、Matthew J. Keough、Peter J. Barelli、Lauren T. Firich、Jonathan E. Hempel、Timothy M. Smith、Rene P.F. Kanters

  DOI：10.1016/j.tet.2009.03.085

  日期：2009.5

  Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt or vinylogous iminium salt derivative. Subsequent transformations of these highly substituted pyrroles lead to efficient

  描述了通过乙烯基亚胺盐衍生物合成层状菌素 G 三甲醚和宁甘素 B 的研究。成功的策略依赖于由乙烯基亚胺盐或乙烯基亚胺盐衍生物形成 2,4-二取代吡咯或 1,2,3,4-四取代吡咯。这些高度取代的吡咯的后续转化导致含有天然产物的相应吡咯的有效和区域受控的形式合成。
• Inhibition of human leukocyte elastase (HLE) by N-substituted peptidyl trifluoromethyl ketones
  作者：Jerry W. Skiles、Victor Fuchs、Clara Miao、Ronald Sorcek、Karl G. Grozinger、Scott C. Mauldin、Jana Vitous、Philip W. Mui、Stephen Jacober

  DOI：10.1021/jm00082a005

  日期：1992.2

  A series of tripeptides possessing trifluoromethyl or aryl ketone residues at P1 were prepared and evaluated both in vitro and in vivo as potential inhibitors of human leukocyte elastase (HLE). Tripeptides containing non naturally occurring N-substituted glycine residues at the P2-position have been demonstrated to be potent in vitro inhibitors of HLE, with IC50 values in the submicromolar range. Sterically demanding substituents on the P2-nitrogen have no detrimental effect on in vitro potency. The inhibition process presumably acts via hemiketal formation with the active site Ser195 of HLE, and is facilitated by the strongly electron withdrawing trifluoromethyl functionality. Deletion of the amino acid at the P3-subsite region affords inactive compounds. Valine is the preferred residue at the P1-position, whereas the corresponding glycine, alanine, alpha,alpha-dimethylglycine, or phenylalanine analogues are all inactive. The compounds described herein all confer a high degree of in vitro specificity when tested against representative cysteine, aspartyl, metallo, and other serine proteases. One of the most potent in vitro inhibitors is (3RS)-N-[4-[[[(4-chlorophenyl)sulfonyl]amino]carbonyl]phenyl]oxomethyl]-L-valyl-N-(2,3-dihydro-1H-inden-2-yl)glycine N-[3-(1,1,1-trifluoro-4-methyl-2-oxopentyl)]amide (20i; BI-RA-260) (IC50 = 0.084-mu-M). Compound 20i was also tested in hamsters in an elastase-induced pulmonary hemorrhage (EPH) model. In this model, intratracheal (it.) administration of 20i, 5 min prior to HLE challenge, effectively inhibited hemorrhage in a dose-dependent manner with an ED50 of 4.8-mu-g. The inhibitor 20i, 20-mu-g administered it. 24, 48, and 72 h prior to HLE challenge, exhibits significant inhibition against hemorrhage at all time points (97%, 64% and 49%, respectively). In a 21-day chronic model of emphysema in hamsters, 200-mu-g of HLE administered it. caused an elastase-induced emphysema in the lungs which can be quantitated histologically utilizing image analysis. In this assay, 20i significantly inhibited pulmonary lesions associated with septal destruction and increased alveolar spaces, when dosed at 20-mu-g it. 5 min prior to challenge with HLE.
• LENNON M.; MCLEAN A.; PROCTOR G. R.; SINCLAIR I. W., J. CHEM. SOC. PERKIN TRANS. <JCPK-BH>, 1975, PART 1, NO 7, 622-626
  作者：LENNON M.、 MCLEAN A.、 PROCTOR G. R.、 SINCLAIR I. W.

  DOI：——

  日期：——