N-phenyl-L-valine | 21671-21-6

• 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-L-valine
• 英文别名: N-phenylvaline；(2S)-2-anilino-3-methylbutanoic acid
• CAS: 21671-21-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: MBRPCSKHPRLQQQ-JTQLQIEISA-N

物化性质

• 熔点：
  118.5-119.0 °C
• 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：

  N-phenyl-L-valine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (S)-N¹-allyl-N¹-benzyl-3-methyl-N²-phenylbutane-1,2-diamine
  参考文献：
  名称：

  A Concise Asymmetric Synthesis of cis-2,6-Disubstituted N-Aryl Piperazines via Pd-Catalyzed Carboamination Reactions

  摘要：

  A concise, modular, asymmetric synthesis of cis-2,6-disubstituted piperazines from readily available amino acid precursors is described. The key step in the synthesis is a Pd-catalyzed carboamination of a N-1-aryl-N-2-allyl-1,2-diamine with an aryl bromide. The products are obtained in 14-20:1 dr, with > 97% ee, and the key cyclizations are the first examples of six-membered ring formation via Pd-catalyzed carboamination reactions of unsaturated amines with aryl halides.

  DOI：

  10.1021/ol071241f
• 作为产物：
  描述：

  L-缬氨酸 在 盐酸 、 sodium nitrite 作用下， 生成 N-phenyl-L-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

• Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides
  申请人：CE Pharm CO., LTD

  公开号：US10500577B2

  公开（公告）日：2019-12-10

  The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.

  本发明提供草酸酰胺配体及其在芳基卤化物的铜催化偶联反应中的应用。具体地，本发明提供了一种由式I表示的化合物的用途，其中每个基团的定义在说明书中描述。式I表示的化合物可用作芳基卤化物的铜催化偶联反应中的配体，用于形成C—N、C—O和C—S键。
• 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。
• 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。
• N-Functionalized Amino Acids Promoted Aerobic Copper-Catalyzed Oxidation of Benzylic Alcohols in Water
  作者：Chengrong Ding、Shang Shan、Guofu Zhang、Jie Lei、Xingwang Han、Yuxin Luan

  DOI：10.1055/s-0034-1380126

  日期：——

  traditional N,N-bidentate ligands, N-functionlized amino acids were used as powerful N,O-bidentate ligands in aerobic copper/TEMPO-catalyzed system for promoting oxidation of benzylic alcohols. Under the optimized reaction conditions, a wide range of primary and secondary benzylic alcohols have been efficiently converted into aldehydes and ketones with good to excellent yields in water.

  代替传统的 N,N-二齿配体，N-官能化氨基酸在有氧铜/TEMPO 催化系统中用作强大的 N,O-二齿配体，以促进苯甲醇的氧化。在优化的反应条件下，广泛的伯醇和仲苄醇已有效地转化为醛和酮，并在水中具有良好到极好的收率。
• Room temperature N-arylation of amino acids and peptides using copper(<scp>i</scp>) and β-diketone
  作者：Krishna K. Sharma、Swagat Sharma、Anurag Kudwal、Rahul Jain

  DOI：10.1039/c5ob00288e

  日期：——

  A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners

  描述了一种用于两性离子氨基酸，氨基酸酯和肽的N-芳基化的温和且有效的方法。该方法提供了第一个室温下使用CuI作为催化剂，二酮作为配体，芳基碘化物作为偶联伴侣的N-芳基化氨基酸和多肽的室温合成方法。该方法同样适用于在80°C下使用相对便宜的芳基溴化物作为偶联伙伴。使用该程序，可以有效地以良好至优异的产率偶联含有反应性官能团的电子和空间上不同的芳基卤化物。