N-(3,4-Dimethoxybenzoyl)-L-phenylalanine | 169887-39-2

• 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
• 英文名称: N-(3,4-Dimethoxybenzoyl)-L-phenylalanine
• 英文别名: (3,4-dimethoxybenzoyl)-L-phenylalanine；(2S)-2-[(3,4-dimethoxybenzoyl)amino]-3-phenylpropanoic acid
• CAS: 169887-39-2
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: QJBNCDHZFCNDLL-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3,4-Dimethoxybenzoyl)-L-phenylalanine 在 sodium hydroxide 、 sodium perborate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成 (2S,3R)-2-(N-(3,4-Dimethoxybenzoyl)amino)-3-methyl-4-phenylhex-5-en-3-ol
  参考文献：
  名称：

  Allylboration of .alpha.-Amino Ketones

  摘要：

  A series of unsaturated alpha-amino alcohols were prepared via the allylboration of the corresponding N-protected alpha-amino ketones. The reactions are stereoselective, producing the syn isomers. The diastereoselectivity is not dramatically effected by the electronic nature of the N-protecting group or the reaction temperature but is dependent on the steric requirements of the N-protecting group and the solvent system.

  DOI：

  10.1021/jo00120a029
• 作为产物：
  描述：

  N-(3,4-Dimethoxybenzoyl)-L-phenylalanine methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以95%的产率得到N-(3,4-Dimethoxybenzoyl)-L-phenylalanine
  参考文献：
  名称：

  Allylboration of .alpha.-Amino Ketones

  摘要：

  A series of unsaturated alpha-amino alcohols were prepared via the allylboration of the corresponding N-protected alpha-amino ketones. The reactions are stereoselective, producing the syn isomers. The diastereoselectivity is not dramatically effected by the electronic nature of the N-protecting group or the reaction temperature but is dependent on the steric requirements of the N-protecting group and the solvent system.

  DOI：

  10.1021/jo00120a029

文献信息

• Palladium-Catalyzed Aminocarbonylation in Solid-Phase Peptide Synthesis: A Method for Capping, Cyclization, and Isotope Labeling
  作者：Anna Skogh、Stig D. Friis、Troels Skrydstrup、Anja Sandström

  DOI：10.1021/acs.orglett.7b01068

  日期：2017.6.2

  A new synthetic approach for introducing N-capping groups onto peptides attached to a solid support, combining aminocarbonylation under mild conditions using a palladacycle precatalyst and solid-phase peptide synthesis, is reported. The use of a silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed in a single vial. The method also enables versatile substitution

  报道了一种新的合成方法，该方法用于在结合有固相支持物的肽上引入N封端基团，并在适度条件下使用Palladacycle预催化剂和固相肽合成方法将氨基羰基化结合在一起。使用硅烷羧酸作为原位释放CO的分子使得反应可以在单个小瓶中进行。该方法还可以实现侧链的通用取代，侧链至侧链的环化以及修饰肽的选择性[ 13 C]酰基标记。
• Allylboration of .alpha.-Amino Ketones
  作者：R. David Pace、George W. Kabalka

  DOI：10.1021/jo00120a029

  日期：1995.7

  A series of unsaturated alpha-amino alcohols were prepared via the allylboration of the corresponding N-protected alpha-amino ketones. The reactions are stereoselective, producing the syn isomers. The diastereoselectivity is not dramatically effected by the electronic nature of the N-protecting group or the reaction temperature but is dependent on the steric requirements of the N-protecting group and the solvent system.