N-acetyl-α,α-dibenzylglycine | 94164-89-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-acetyl-α,α-dibenzylglycine
• 英文别名: 2-acetylamino-2-benzyl-3-phenyl-propionic acid；2-Acetylamino-2-benzyl-3-phenyl-propionsaeure；2-Acetamino-2-benzyl-3-phenyl-propionsaeure；N-Acetyl-I+/--(phenylmethyl)phenylalanine；2-acetamido-2-benzyl-3-phenylpropanoic acid
• CAS: 94164-89-3
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: WLOHJKKEBVMOKH-UHFFFAOYSA-N

物化性质

• 熔点：
  233-235 °C
• 沸点：
  527.0±50.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  N-acetyl-α,α-dibenzylglycine 在 氢溴酸 作用下， 反应 2.0h， 以96%的产率得到2-氨基-2-苄基-3-苯基丙酸
  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
• 作为产物：
  描述：

  二苄基甲酮 在 三氟乙酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 N-acetyl-α,α-dibenzylglycine
  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.
• Felkin, Bulletin de la Societe Chimique de France, 1959, p. 20,30
  作者：Felkin

  DOI：——

  日期：——
• 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/
  作者：Susana P. G. Costa、Hernâni L. S. Maia、Sílvia M. M. A. Pereira-Lima

  DOI：10.1039/b212473b

  日期：2003.4.23

  A general and simple strategy for routine peptide synthesis with α,α-dialkyl glycines taking advantage of the four-component Ugi–Passerini reaction is presented. The isonitrile required for the reaction can be relatively simple and its selection based on cost, as the group it generates is easily removed under acidic conditions; in addition, this removal is not visibly affected by the bulkiness of the α-alkyl groups. Being a good leaving group from the N-terminal amino group of the amino acid, 4-methoxybenzyl was the choice for the amine component of the reaction. The method is illustrated with the synthesis of a series of acyl derivatives of several α,α-dialkyl glycines. The preparation of the latter compounds is also reported.

  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。