(S)-3-[4-(4-acetylphenoxy)phenyl]-2-tert-butoxycarbonylaminopropionic acid methyl ester

• 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)-3-[4-(4-acetylphenoxy)phenyl]-2-tert-butoxycarbonylaminopropionic acid methyl ester
• 英文别名: methyl (2S)-3-[4-(4-acetylphenoxy)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: MJUGCUKPAYHSAI-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 、 Boc-L-酪氨酸 、 碘甲烷 在 copper(l) iodide 、 N,N-二甲基甘氨酸盐酸盐 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以60%的产率得到(S)-3-[4-(4-acetylphenoxy)phenyl]-2-tert-butoxycarbonylaminopropionic acid methyl ester
  参考文献：
  名称：

  Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives

  摘要：

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.

  DOI：

  10.1021/jo0606960

文献信息

• Mild and Nonracemizing Conditions for Ullmann-type Diaryl Ether Formation between Aryl Iodides and Tyrosine Derivatives
  作者：Qian Cai、Gang He、Dawei Ma

  DOI：10.1021/jo0606960

  日期：2006.7.1

  [GRAPHICS]CuI/N,N-dimethylglycine-catalyzed coupling reaction of L-tyrosine derivatives and L-phenylalanine-derived iodides in the presence of Cs2CO3 works at 90 degrees C to provide the corresponding diaryl ether. Partial racemization occurs when N-Boc- and N-Cbz-protected aromatic amino esters are used, while N-trityl-and N,N-dibenzyl-protected aromatic amino esters give rise to coupling products without loss of optical purity. Little racemization is also observed in cases of N-Boc- and N-Cbz- protected aromatic amino acids as substrates. But their reaction yields are moderate. On the basis of these studies, shorter protocols for assembling (S,S)-isodityrosine and K-13 are developed.