3-羟基-4-甲氧基-L-苯丙氨酸甲酯 | 37466-41-4

• 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
• 中文名称: 3-羟基-4-甲氧基-L-苯丙氨酸甲酯
• 英文名称: 3-hydroxy-O-methyl-L-tyrosine methyl ester
• 英文别名: 3-Hydroxy-4-methoxy-L-phenylalanine methyl ester；methyl (2S)-2-amino-3-(3-hydroxy-4-methoxyphenyl)propanoate
• CAS: 37466-41-4
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: AKOBVLCFNXIOQK-QMMMGPOBSA-N

物化性质

• 沸点：
  360.6±37.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-羟基-4-甲氧基-L-苯丙氨酸甲酯 在 samarium diiodide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 (S)-3-<4-<2-Carboxy-2-<<(1,1-dimethylethoxy)carbonyl>amino>ethyl>phenoxy>-O-methyl-N--L-tyrosinyl>-L-tyrosine α-methyl ester
  参考文献：
  名称：

  A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

  摘要：

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.

  DOI：

  10.1021/jo00088a009
• 作为产物：
  描述：

  3-乙酰基-N-苄氧羰基-L-酪氨酸甲酯 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0~40.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 3-羟基-4-甲氧基-L-苯丙氨酸甲酯
  参考文献：
  名称：

  (+)-哌嗪霉素的全合成

  摘要：

  (+)-哌嗪霉素 (1) 是一种具有抗微生物和抗真菌活性的新型天然大环哌嗪的简明全合成，详细介绍了对二酮哌嗪 (53%) 进行的改进的 Ullmann 大环化反应的实施

  DOI：

  10.1021/ja00077a047

文献信息

• Total synthesis of cycloisodityrosine, RA-VII, deoxybouvardin, and N29-desmethyl-RA-VII: Identification of the pharmacophore and reversal of the subunit functional roles
  作者：Dale L. Boger、Daniel Yohannes、Jiacheng Zhou、Michael A. Patane

  DOI：10.1021/ja00062a004

  日期：1993.5

  Full details of a concise total synthesis of RA-VII (1) and deoxybouvardin (2) are described based on the implementation of an effective intramolecular Ullmann reaction as the key macrocyclization reaction in the preparation of the elusive 14-membered cycloisodityrosine subunit (33) of the bicyclic hexapeptides. Subsequent coupling of 34 to tetrapeptide 17 and macrocyclization with C 2 -N 3 amide bond

  基于有效的分子内 Ullmann 反应作为制备难以捉摸的 14 元环异二酪氨酸亚基 (33) 的关键大环化反应的实施，描述了 RA-VII (1) 和脱氧布瓦丁 (2) 的简明全合成的全部细节的双环六肽。随后 34 与四肽 17 偶联以及大环化与 C 2 -N 3 酰胺键形成提供了 1 和 2。在解决有助于其抗肿瘤活性的药物的关键结构和构象特征的努力中，N 29 -去甲基-RA-制备了 VII 并详细说明了其化学、构象和初步生物学特性
• Intramolecular Ullmann condensation reaction: an effective approach to macrocyclic diaryl ethers
  作者：Dale L. Boger、D. Yohannes

  DOI：10.1021/jo00005a020

  日期：1991.3

  The demonstration and definition of the scope of the intramolecular Ullmann condensation reaction suitable for use in macrocyclization reactions leading to 14-membered para- and metacyclophanes possessing a diaryl ether are detailed.
• Synthesis of N29-desmethyl RA-VII. Identification of the pharmacophore of RA-I-VII and deoxybouvardin and reassignment of the subunit functional roles
  作者：Dale L. Boger、Daniel Yohannes、James B. Myers

  DOI：10.1021/jo00031a001

  日期：1992.2

  N29-Desmethyl RA-VII was prepared in efforts that address the key structural and conformational features of the agent that contribute to its antitumor activity.
• A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis
  作者：Anthony J. Pearson、Kieseung Lee

  DOI：10.1021/jo00088a009

  日期：1994.5

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.
• Total synthesis of (+)-Piperazinomycin
  作者：Dale L. Boger、Jiacheng Zhou

  DOI：10.1021/ja00077a047

  日期：1993.12

  A concise total synthesis of (+)-piperazinomycin (1), a novel naturally occurring macrocyclic piperazine possessing antimicrobial and antifungal activity, is detailed with implementation of an improved Ullmann macrocyclization reaction conducted on a diketopiperazine (53%)

  (+)-哌嗪霉素 (1) 是一种具有抗微生物和抗真菌活性的新型天然大环哌嗪的简明全合成，详细介绍了对二酮哌嗪 (53%) 进行的改进的 Ullmann 大环化反应的实施