ethyl N-benzoylalaninate | 43008-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl N-benzoylalaninate
• 英文别名: N-benzoyl-D-alanine ethyl ester；ethyl (2R)-2-benzamidopropanoate
• CAS: 43008-70-4
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: OJNMULJHNFYKCF-SECBINFHSA-N

物化性质

• 沸点：
  393.7±25.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-benzoylalaninate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N-[(2R)-1-hydrazinyl-1-oxopropan-2-yl]benzamide
  参考文献：
  名称：

  硫属键合介导晶体中氮杂肽超分子螺旋的形成

  摘要：

  为了探索硫族键合是否能够驱动超分子螺旋的形成，含有β-转角结构的丙氨酸氮杂肽，分别在N-或C-末端掺入噻吩基团，被用作螺旋结构单元。前者衍生物通过晶体中的分子间S⋯S硫族键合形成超分子M-螺旋，后者通过分子间S⋯O硫族键合形成P-螺旋。

  DOI：

  10.1039/d1ob01053k
• 作为产物：
  描述：

  苯甲酰基-DL-alpha-丙氨酸乙酯 在 Mesityl-Li 、 1-[5'-toluenesulfonyl-2'-(methylamino)phenyl]-1,2,3,4-tetrahydroisoquinoline 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.0h， 生成 ethyl benzoyl-L-alaninate 、 ethyl N-benzoylalaninate
  参考文献：
  名称：

  Enantioselective Enolate Protonation:  Matching Chiral Aniline and Substrate Acidity

  摘要：

  A comparison of chiral anilines 1a-f in the asymmetric protonation of enolate 15 shows that the optimum Delta pK(a) value (chiral acid vs protonated enolate) for the highest enantioselectivity is ca. 3 (Table 2). An extension of this concept to amino acid enolates was possible, and le was found to give the best enantioselectivity (85% ee) with the alanine-derived N-lithioenolate 5a (Table 3). Changes in aniline pK(a) due to variation of substituents at the aniline nitrogen were evaluated briefly, but these changes did not show consistent trends in the enantioselectivity vs pK(a).

  DOI：

  10.1021/jo990897m

文献信息

• Enantioselective Benzoylation of α-Amino Esters Using (<i>S</i>)-1-Benzoyl-2- (α-acetoxyethyl)benzimidazole, a Chiral Benzimidazolide
  作者：Anil V. Karnik、Suchitra S. Kamath

  DOI：10.1021/jo070962p

  日期：2007.9.1

  [GRAPHICS]A new chiral benzimidazolide is developed as a nonenzymatic acylating agent for enantioselective benzoylation of racemic cc-amino esters. The process is highly efficient, which exhibits uniformly high enantioselectivity for alpha-amino esters with or without aryl substituents under mild reaction conditions. The chiral benzimidazolide is inexpensive and is easily accessible.
• Chalcogen bonding mediates the formation of supramolecular helices of azapeptides in crystals
  作者：Di Shi、Jinlian Cao、Peimin Weng、Xiaosheng Yan、Zhao Li、Yun-Bao Jiang

  DOI：10.1039/d1ob01053k

  日期：——

  drive the formation of supramolecular helices, alanine-based azapeptides containing a β-turn structure, with a thiophene group, respectively, incorporated in the N- or C-terminus, were employed as helical building blocks. While the former derivative formed a supramolecular M-helix via intermolecular S⋯S chalcogen bonding in crystals, the latter formed P-helix via intermolecular S⋯O chalcogen bonding.

  为了探索硫族键合是否能够驱动超分子螺旋的形成，含有β-转角结构的丙氨酸氮杂肽，分别在N-或C-末端掺入噻吩基团，被用作螺旋结构单元。前者衍生物通过晶体中的分子间S⋯S硫族键合形成超分子M-螺旋，后者通过分子间S⋯O硫族键合形成P-螺旋。
• Enantioselective Enolate Protonation:  Matching Chiral Aniline and Substrate Acidity
  作者：E. Vedejs、A. W. Kruger、E. Suna

  DOI：10.1021/jo990897m

  日期：1999.10.1

  A comparison of chiral anilines 1a-f in the asymmetric protonation of enolate 15 shows that the optimum Delta pK(a) value (chiral acid vs protonated enolate) for the highest enantioselectivity is ca. 3 (Table 2). An extension of this concept to amino acid enolates was possible, and le was found to give the best enantioselectivity (85% ee) with the alanine-derived N-lithioenolate 5a (Table 3). Changes in aniline pK(a) due to variation of substituents at the aniline nitrogen were evaluated briefly, but these changes did not show consistent trends in the enantioselectivity vs pK(a).