(S)-4-methoxy-N-benzoyl-phenylalanine-methylester | 18217-57-7

• 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: (S)-4-methoxy-N-benzoyl-phenylalanine-methylester
• 英文别名: methyl 2-benzamido-3-(4-methoxyphenyl)propanoate；N-benzoyl-O-methyl-L-tyrosine methyl ester；N-Benzoyl-O-methyl-L-tyrosin-methylester；methyl (2S)-2-benzamido-3-(4-methoxyphenyl)propanoate
• CAS: 18217-57-7
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: QLDSDWMNLKMNRN-INIZCTEOSA-N

物化性质

• 熔点：
  55-56 °C
• 沸点：
  526.6±45.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 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：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-methoxy-N-benzoyl-phenylalanine-methylester 在 methyllithium lithium bromide 、 三甲基铝 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  通过手性1,3-恶嗪全合成甲基1-柔磺酰胺盐酸盐

  摘要：

  从容易获得的1-酪氨酸实现了甲基1-柔香胺素盐酸盐的全合成。该策略的关键步骤是钯（0）催化的立体选择性分子内恶嗪的形成和恶嗪中间体的催化加氢。本文报道了甲基1-柔红酰胺盐酸盐的α-和β-端基异构体的1 H和13 C NMR数据。

  DOI：

  10.1016/j.tet.2014.02.033
• 作为产物：
  描述：

  甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酰氯 作用下， 生成 (S)-4-methoxy-N-benzoyl-phenylalanine-methylester
  参考文献：
  名称：

  Cornforth, Chemistry of Penicillin

  摘要：

  DOI：

文献信息

• A new type of chiral-pyridoxamines for catalytic asymmetric transamination of α-keto acids
  作者：Jianfeng Chen、Junyu Zhao、Xing Gong、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2016.09.005

  日期：2016.10

  A new type of chiral pyridoxamines bearing an adjacent chiral stereocenter has been developed via multi-step synthesis. The pyridoxamines displayed catalytic activity in asymmetric transamination of α-keto acids to give a variety of optically active amino acids in 27–78% yields with 34–62% ee’s under very mild conditions. This work provides a synthetic strategy to construct new chiral pyridoxamines

  通过多步合成已经开发了一种新型的带有相邻手性立体中心的手性吡ido胺。吡ido胺在非常温和的条件下，在α-酮酸的不对称转氨反应中显示出催化活性，从而以27-78％的产率提供了34-62％ee的多种光学活性氨基酸。这项工作提供了使用溴吡啶7作为关键合成子来构建新的手性吡ido胺的合成策略，也代表了手性吡x胺在不对称催化中的早期应用实例。
• Unusual amino acids III. Asymmetric synthesis of 3-arylalanines
  作者：Stefan Taudien、Klaus Schinkowski、Hans-Walter Krause

  DOI：10.1016/s0957-4166(00)86017-6

  日期：1993.1

  21 (Z)-alpha-N-benzoylamino-beta-arylacrylic acids and their esters were prepared by known procedures and hydrogenated to the corresponding optically active alpha-benzoyl-beta-arylalanine derivatives with optical yields in the range of 82-95% ee using the cationic rhodium complex of ''PROPRAPHOS'' as the chiral catalyst No electronical influences of the substituents at the aryl moiety on the enantioselectivity were observed but a sterical one, proved by X-ray crystallographic analysis and computer-aided modellings. Deacylation of the hydrogenated spezies produced the hydrochlorides of the 3-arylalanines attended by a partial racemisation In this case the hydrogenation of urethane type protected dehydroaminoacid derivatives seems to be the alternative.
• Total synthesis of methyl l-daunosaminide hydrochloride via chiral 1,3-oxazine
  作者：Tian Jin、Jin-Seok Kim、Yu Mu、Seok-Hwi Park、Xiangdan Jin、Jong-Cheol Kang、Chang-Young Oh、Won-Hun Ham

  DOI：10.1016/j.tet.2014.02.033

  日期：2014.4

  Total synthesis of methyl l-daunosaminide hydrochloride was achieved from readily available l-tyrosine. Key steps in this strategy were palladium(0) catalyzed stereoselective intramolecular oxazine formation and catalytic hydrogenation of oxazine intermediate. This paper reported 1H and 13C NMR data of α- and β-anomer of methyl l-daunosaminide hydrochloride.

  从容易获得的1-酪氨酸实现了甲基1-柔香胺素盐酸盐的全合成。该策略的关键步骤是钯（0）催化的立体选择性分子内恶嗪的形成和恶嗪中间体的催化加氢。本文报道了甲基1-柔红酰胺盐酸盐的α-和β-端基异构体的1 H和13 C NMR数据。
• Cornforth, Chemistry of Penicillin
  作者：Cornforth

  DOI：——

  日期：——