(S)-2-(4-Chloro-benzylamino)-4-methyl-pentanoic acid ethyl ester | 834883-67-9

• 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
• 英文名称: (S)-2-(4-Chloro-benzylamino)-4-methyl-pentanoic acid ethyl ester
• 英文别名: ethyl (2S)-2-[(4-chlorophenyl)methylamino]-4-methylpentanoate
• CAS: 834883-67-9
• 化学式: C₁₅H₂₂ClNO₂
• 分子量: 283.798
• InChiKey: WYYQKNQRKZPSIM-AWEZNQCLSA-N

物化性质

• 沸点：
  359.3±27.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (S)-2-(4-Chloro-benzylamino)-4-methyl-pentanoic acid ethyl ester 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 7.0h， 以78%的产率得到(S)-2-[Acetyl-(4-chloro-benzyl)-amino]-4-methyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  N-Benzyl Derivatives of Leucine Esters

  摘要：

  Leucine methyl and ethyl esters reacted with 3-bromobenzaldehyde and 4-chlorobenzaldehyde in anhydrous methanol in the presence of magnesium sulfate to afford the coresponding Schiff bases of the general formula (CH3)(2)CHCH2CH(COOR1)N=CHR2 [R-1 = CH3, C2H5, R-2 = 3-BrC6H4, 4-ClC6H4]. Their reduction with sodium tetrahydridoborate yielded N-benzyl derivatives (CH3)(2)CHCH2CH(COOR1)NHCH2R2, which were converted into N-acyl-N-benzyl derivatives (CH3)(2)CHCH2CH(COOR1)N(COR3)CH2R2 [R-3 = CH3, C6H5].

  DOI：

  10.1023/b:rujo.0000034963.96456.70
• 作为产物：
  描述：

  L-亮氨酸乙酯 在 sodium tetrahydroborate 、 magnesium sulfate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 48.0h， 生成 (S)-2-(4-Chloro-benzylamino)-4-methyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  N-Benzyl Derivatives of Leucine Esters

  摘要：

  Leucine methyl and ethyl esters reacted with 3-bromobenzaldehyde and 4-chlorobenzaldehyde in anhydrous methanol in the presence of magnesium sulfate to afford the coresponding Schiff bases of the general formula (CH3)(2)CHCH2CH(COOR1)N=CHR2 [R-1 = CH3, C2H5, R-2 = 3-BrC6H4, 4-ClC6H4]. Their reduction with sodium tetrahydridoborate yielded N-benzyl derivatives (CH3)(2)CHCH2CH(COOR1)NHCH2R2, which were converted into N-acyl-N-benzyl derivatives (CH3)(2)CHCH2CH(COOR1)N(COR3)CH2R2 [R-3 = CH3, C6H5].

  DOI：

  10.1023/b:rujo.0000034963.96456.70

文献信息

• Direct Catalytic <i>N</i> ‐Alkylation of α‐Amino Acid Esters and Amides Using Alcohols with High Retention of Stereochemistry
  作者：Tao Yan、Ben L. Feringa、Katalin Barta

  DOI：10.1002/cssc.202100373

  日期：2021.6.8

  naturally abundant chiral scaffolds such as α-amino acid esters or amides with widely abundant alcohols, without any racemization, is a demanding transformation that is of central importance for the synthesis of bio-active compounds. Herein a robust and general method was developed for the direct N-alkylation of α-amino acid esters and amides with alcohols. This powerful ruthenium-catalyzed methodology

  天然丰富的手性支架（例如α-氨基酸酯或酰胺）与广泛丰富的醇的直接官能化，无需任何外消旋作用，是一个要求很高的转化，对于生物活性化合物的合成至关重要。本文开发了一种稳健且通用的方法，用于 α-氨基酸酯和酰胺与醇的直接N-烷基化。这种强大的钌催化方法是原子经济的、无碱的，并且可以很好地保留立体化学完整性。使用磷酸二苯酯作为添加剂对于显着提高反应活性和产物选择性至关重要。值得注意的是，唯一的副产品是水，两种底物都可能来自可再生资源。
• N-Benzyl Derivatives of Leucine Esters
  作者：L. A. Popova、N. Ya. Yurashevich、V. A. Knizhnikov

  DOI：10.1023/b:rujo.0000034963.96456.70

  日期：2004.3

  Leucine methyl and ethyl esters reacted with 3-bromobenzaldehyde and 4-chlorobenzaldehyde in anhydrous methanol in the presence of magnesium sulfate to afford the coresponding Schiff bases of the general formula (CH3)(2)CHCH2CH(COOR1)N=CHR2 [R-1 = CH3, C2H5, R-2 = 3-BrC6H4, 4-ClC6H4]. Their reduction with sodium tetrahydridoborate yielded N-benzyl derivatives (CH3)(2)CHCH2CH(COOR1)NHCH2R2, which were converted into N-acyl-N-benzyl derivatives (CH3)(2)CHCH2CH(COOR1)N(COR3)CH2R2 [R-3 = CH3, C6H5].