N-phenyl-D-valine | 185533-07-7

• 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-phenyl-D-valine
• 英文别名: phenyl-D-valine；(2R)-3-Methyl-2-(phenylamino)butanoic acid；(2R)-2-anilino-3-methylbutanoic acid
• CAS: 185533-07-7
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: MBRPCSKHPRLQQQ-SNVBAGLBSA-N

物化性质

• 沸点：
  366.2±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Bis-(N-methylacetamido)-methylphenylsilan 、 N-phenyl-D-valine 以 苯 为溶剂， 生成 (-)-2-Methyl-4-isopropyl-2,3-diphenyl-2-siloxazolidon-(5)
  参考文献：
  名称：

  Optically active silicon in 2-siloxazolidones-5. An asymmetric synthesis

  摘要：

  DOI：

  10.1021/ja01028a014
• 作为产物：
  描述：

  2-溴代异戊酸 、 苯胺 生成 N-phenyl-D-valine
  参考文献：
  名称：

  Optically active silicon in 2-siloxazolidones-5. An asymmetric synthesis

  摘要：

  DOI：

  10.1021/ja01028a014

文献信息

• Copper-catalyzed aryl amination in aqueous media with 2-dimethylaminoethanol ligand
  作者：Zhikuan Lu、Robert J. Twieg

  DOI：10.1016/j.tetlet.2005.03.027

  日期：2005.4

  Copper-catalyzed amination of aryl bromides and iodides under mild conditions has been developed with 2-dimethylaminoethanol as ligand and water as solvent. A variety of hydrophilic and hydrophobic aryl halide substrates have been aminated in good yield with a variety of amino acids, amino alcohols and peptides. This method has successfully N-arylated some hydrophilic amino compounds not available

  以2-二甲基氨基乙醇为配体，水为溶剂，在温和条件下进行了铜催化的芳基溴化物和碘化物的胺化反应。各种亲水性和疏水性芳基卤化物底物均已与各种氨基酸，氨基醇和肽以高收率胺化。该方法已成功地使一些其他方法无法获得的亲水性氨基化合物N-芳基化。
• Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol
  作者：Fangyu Du、Qifan Zhou、Yang Fu、Yuanguang Chen、Ying Wu、Guoliang Chen

  DOI：10.1055/s-0039-1690707

  日期：2019.12

  Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C–N coupling reactions proceed under mild conditions and exhibit good functional group tolerance

  在本文中，我们报告了天然配体 quebrachitol (QCT) 作为 Cu(II) 催化剂的促进剂，它对各种胺和相关芳基卤化物的 N-芳基化非常有效。通过使用二甘醇（DEG）作为配体和溶剂，以高收率获得了一系列二芳胺衍生物。C-N偶联反应在温和的条件下进行并表现出良好的官能团耐受性。
• Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
  作者：Yuanguang Chen、Fangyu Du、Fengyang Chen、Qifan Zhou、Guoliang Chen

  DOI：10.1055/s-0039-1690702

  日期：2019.12

  selective N-arylation of amines or azoles with aryl halides­, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and

  在胺或唑与芳基卤的选择性N-芳基化反应中，发现甲基-α - d-吡喃葡萄糖苷（MG）作为铜粉的绿色配体起作用。另外，氮杂环胺化合物还可与杂环芳基氯进行N-芳基化偶联。该方法允许在温和的反应条件下获得各种芳族胺和芳基唑，具有良好的耐受性，并且以中等至高收率进行。
• Palladium-catalyzed coupling reaction of amino acids (esters) with aryl bromides and chlorides
  作者：Fangfang Ma、Xiaomin Xie、Lina Ding、Jinsheng Gao、Zhaoguo Zhang

  DOI：10.1016/j.tet.2011.09.109

  日期：2011.12

  showed high efficiency for the coupling reactions of amino acids and inactive aryl halides to give N-aryl amino acids. Under the catalytic conditions, not only α-amino acids, but also β-, γ-, and δ-amino acids have been coupled with aryl chlorides in moderate to high yields; in the case of optically pure β-amino acids as substrates, the optical purities of the coupling products retained.

  庞大且富电子的MOP型配体和Pd（dba）2组合对氨基酸与非活性芳基卤化物的偶合反应显示出N-芳基氨基酸的高效反应。在催化条件下，不仅α-氨基酸，而且β-，γ-和δ-氨基酸都以中等至高收率与芳基氯偶合。在光学纯的β-氨基酸作为底物的情况下，保留了偶联产物的光学纯度。
• Accelerating Effect Induced by the Structure of α-Amino Acid in the Copper-Catalyzed Coupling Reaction of Aryl Halides with α-Amino Acids. Synthesis of Benzolactam-V8
  作者：Dawei Ma、Yongda Zhang、Jiangchao Yao、Shihui Wu、Fenggang Tao

  DOI：10.1021/ja981662f

  日期：1998.12.1

  hydrophilic groups. No racemization was observed in most cases of this coupling reaction. After some controlled experiments, a possible mechanism including the π-complex and the intramolecular substitution reaction is proposed. Based on this catalyzed reaction, a facile and stereoselective synthesis of benzolactam-V8, a new PKC activator, is achieved.

  光学纯的 α-氨基酸与芳基卤化物的偶联产生对映纯的 N-芳基-α-氨基酸，在 CuI 的催化下保留构型。即使对于富电子的芳基卤化物，该反应也可以在比典型的 Ullmann 缩合低得多的温度下完成，这表明该反应中存在由 α-氨基酸结构诱导的加速效应。具有较大疏水基团的α-氨基酸产生较高的偶联产率，而具有较小疏水基团的α-氨基酸仅产生较低的产率，并且对于具有亲水基团的那些没有检测到偶联产物。在该偶联反应的大多数情况下未观察到外消旋化。经过一些对照实验，提出了一种可能的机制，包括 π 络合物和分子内取代反应。