N-(2'-hydroxymethylphenyl)-L-valine | 219645-03-1

• 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-(2'-hydroxymethylphenyl)-L-valine
• 英文别名: (2S)-2-[2-(hydroxymethyl)anilino]-3-methylbutanoic acid
• CAS: 219645-03-1
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: OWRKXNOLABOXRA-NSHDSACASA-N

物化性质

• 沸点：
  446.8±35.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2'-hydroxymethylphenyl)-L-valine 在 aluminum oxide 、 potassium carbonate 、 三乙胺 、 pyridinium chlorochromate 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  ASYMMETRIC INTRAMOLECULAR CONJUGATE ADDITION OF α-AMINO ACID DERIVATIVES VIA RACEMIZATION-FREE EQUILIBRIUM OF INTERMEDIARY CHIRAL ENOLATES

  摘要：

  A highly enantioselective route to a multi-substituted indoline derivative via intramolecular conjugate addition of an a-amino acid derivative has been developed. Enantioselectivity of the reaction was almost independent from the temperature, while the diastereoselectivity was totally dependent on the temperature. High diastereomeric ratios observed at the higher temperatures were assumed to be the results from an equilibrium process between axially chiral enolate intermediates.

  DOI：

  10.3987/com-12-s(n)129
• 作为产物：
  描述：

  L-缬氨酸 、 2-碘苄醇 在 copper(l) iodide 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以100%的产率得到N-(2'-hydroxymethylphenyl)-L-valine
  参考文献：
  名称：

  应用不对称叠氮化法合成（-）-苯并内酰胺-V8

  摘要：

  （−）-Benzolactam-V8是由人为设计的环状二肽，具有很强的肿瘤促进活性，是通过苄基（S）-N-（2-甲酰基苯基）-N-甲基缬氨酸盐通过应用胍基内鎓盐参与的不对称叠氮化而合成的由3-芳基氮丙啶-2-羧酸酯的还原性开环反应形成。

  DOI：

  10.1016/j.tet.2011.11.033

文献信息

• 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。
• Preparation of<i>N</i>-Aryl Compounds by Amino Acid-Promoted Ullmann-Type Coupling Reactions
  作者：Dawei Ma、Qian Cai、Wei Zhu、Hui Zhang、Yongda Zhang

  DOI：10.1055/s-2004-831196

  日期：——

  N-Aryl alpha- or beta-amino acids, aryl amines, N-arylpyrroles, N-arylindoles, N-arylimidazoles, N-arylpyrazoles and aryl azides are prepared by CuI-catalyzed coupling reactions of aryl halides with corresponding nitrogen sources using amino acids as the promoters.

  N-芳基α-或β-氨基酸、芳基胺、N-芳基吡咯、N-芳基吲哚、N-芳基咪唑、N-芳基吡唑和芳基叠氮化物通过使用氨基酸的芳基卤化物与相应氮源的CuI催化偶联反应制备作为发起人。
• ASYMMETRIC INTRAMOLECULAR CONJUGATE ADDITION OF α-AMINO ACID DERIVATIVES VIA RACEMIZATION-FREE EQUILIBRIUM OF INTERMEDIARY CHIRAL ENOLATES
  作者：Takeo Kawabata、Daiki Monguchi、Tomoyuki Yoshimura、Kazuyuki Irie、Kazuhiro Hayashi、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.3987/com-12-s(n)129

  日期：——

  A highly enantioselective route to a multi-substituted indoline derivative via intramolecular conjugate addition of an a-amino acid derivative has been developed. Enantioselectivity of the reaction was almost independent from the temperature, while the diastereoselectivity was totally dependent on the temperature. High diastereomeric ratios observed at the higher temperatures were assumed to be the results from an equilibrium process between axially chiral enolate intermediates.
• Synthesis of (−)-benzolactam-V8 by application of asymmetric aziridination
  作者：Itsara Khantikaew、Masato Takahashi、Takuya Kumamoto、Noriyuki Suzuki、Tsutomu Ishikawa

  DOI：10.1016/j.tet.2011.11.033

  日期：2012.1

  (−)-Benzolactam-V8, an artificially-designed cyclic dipeptide with strong tumor-promoter activity, was synthesized from benzyl (S)-N-(2-formylphenyl)-N-methylvalinate by application of guanidinium ylide-participated asymmetric aziridination followed by the reductive ring-opening reaction of 3-arylaziridine-2-carboxylate formed.

  （−）-Benzolactam-V8是由人为设计的环状二肽，具有很强的肿瘤促进活性，是通过苄基（S）-N-（2-甲酰基苯基）-N-甲基缬氨酸盐通过应用胍基内鎓盐参与的不对称叠氮化而合成的由3-芳基氮丙啶-2-羧酸酯的还原性开环反应形成。