2-乙酰氨基-2-乙基丁酸 | 139578-94-2

• 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: 2-乙酰氨基-2-乙基丁酸
• 中文别名: 丁酸,2-(乙酰基氨基)-2-乙基-
• 英文名称: N-Acetyl-C^α,α-diethylglycine
• 英文别名: N-acetyl-α,α-diethylglycine；2-acetylamino-2-ethyl-butyric acid；2-Acetylamino-2-aethyl-buttersaeure；2-Acetamino-2-aethyl-buttersaeure；Acetamino-diaethyl-essigsaeure；2-Acetamido-2-ethylbutanoic acid
• CAS: 139578-94-2
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: KEWRXJBFHLPAOL-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211 °C
• 沸点：
  369.6±25.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-2-乙基丁酸 在 硫酸 作用下， 生成 2-氨基-2-乙基丁酸
  参考文献：
  名称：

  Felkin, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 227, p. 510

  摘要：

  DOI：
• 作为产物：
  描述：

  N-acetyl-N-(4-methoxybenzyl)-α,α-diethylglycine 4-methoxyphenyl amide 在 三氟乙酸 作用下， 以94%的产率得到2-乙酰氨基-2-乙基丁酸
  参考文献：
  名称：

  An improved approach for the synthesis of α,α-dialkyl glycine derivatives by the Ugi–Passerini reactionElectronic supplementary information (ESI) available: spectroscopic data for compounds 1-5. See http://www.rsc.org/suppdata/ob/b2/b212473b/

  摘要：

  本文提出了一种利用四组分Ugi-Passerini反应进行常规α,α-二烷基甘氨酸肽合成的一般且简单策略。反应所需异氰化物可以相对简单，其选择基于成本，因为它所生成的基团在酸性条件下易于去除；此外，这种去除并不明显受到α-烷基基团大小的影响。4-甲氧基苄基作为氨基酸N端氨基的良好离去基团，被选作反应中的胺组分。该方法通过合成几种α,α-二烷基甘氨酸的酰基衍生物系列进行了说明。还报道了后者的制备。

  DOI：

  10.1039/b212473b

文献信息

• Straightforward, racemization-free synthesis of peptides with fairly to very bulky di- and trisubstituted glycines
  作者：Filipa C.S.C. Pinto、Sílvia M.M.A. Pereira-Lima、Hernâni L.S. Maia

  DOI：10.1016/j.tet.2009.09.022

  日期：2009.11

  Several fully protected tri- and pentapeptides containing a central symmetrical alpha,alpha-dialkyl glycine residue, with the alkyl group varying from methyl or ethyl to benzyl, were synthesized in good yields by a strategy based on the Ugi-Passerini reaction. Each Ugi-Passerini adduct was selectively cleaved and the product submitted to an assisted N,N'-dicyclohehylcarbodiimide coupling to an amino acid or dipeptide ester, respectively. Tripeptides as the above but containing a 4-methoxybenzyl group at the nitrogen atom of the central residue were also synthesized in fair to good yields by N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide assisted couplings. The results reported here show that our strategy is appropriate for routine synthesis of peptides incorporating these moieties. (C) 2009 Elsevier Ltd. All rights reserved.
• Galdecki, Zdzislaw; Luciak, Bernard; Redlinski, Adam S., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1992, vol. 47, # 1, p. 90 - 92
  作者：Galdecki, Zdzislaw、Luciak, Bernard、Redlinski, Adam S.、Kacmarek, Krzysztof、Leplawy, Miroslaw T.

  DOI：——

  日期：——
• Synthesis, crystal structure and conformation of N-acetyl-Cα,α-diethylglycine-N′-methylamide
  作者：Zdzisław Gałdecki、Bernard Luciak、Krzysztof Kaczmarek、Mirosław T. Leplawy、Adam S. Redliński

  DOI：10.1007/bf00810930

  日期：1992.11

  Synthesis and X-ray structure analysis of N-acetyl-C(alpha, alpha)-diethylglycine-N'-methylamide [CH3 - CO - NH - C(C2H5)2- CO - NHCH3] are described. The compound was obtained from the corresponding N-acetyl derivative [CH3 - CO - NH - C(C2H5)2 - COOH] through the mixed anhydride procedure. It crystallizes as monohydrate (C9H18N2O2.H2O) in space group P2(1)/c, a = 7.139(1), b = 11.823(2), c = 15.778(3) angstrom, beta = 122.23(1)-degrees, V= 1126.53 angstrom3, D(m) = 1.20 Mgm-3 (room temperature), R = 0.046 for 1523 reflections. The crystal packing is dominated by two strong hydrogen bonds between the water molecule and two carbonyl oxygen atoms and two weak H-bonds to two amide-N-atoms of symmetry-equivalent molecules. The molecular conformation is closer to a 3(10)-helix then an alpha-helix.