methyl (2R)-2-acetamido-3-(4-hydroxyphenyl)propanoate | 65160-71-6

• 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: methyl (2R)-2-acetamido-3-(4-hydroxyphenyl)propanoate
• CAS: 65160-71-6
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: KRMVXLWZDYZILN-LLVKDONJSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  457.0±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-acetamido-3-(4-hydroxyphenyl)propanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 (R)-2-Acetylamino-3-{4-[3-((R)-amino-methoxycarbonyl-methyl)-phenoxy]-phenyl}-propionic acid methyl ester
  参考文献：
  名称：

  Studies on the synthesis of aryl ethers using arene-manganese chemistry

  摘要：

  Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described. The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schollkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes. Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.

  DOI：

  10.1021/jo00025a026
• 作为产物：
  描述：

  D-酪氨酸甲酯 以68%的产率得到methyl (2R)-2-acetamido-3-(4-hydroxyphenyl)propanoate
  参考文献：
  名称：

  Studies on the synthesis of aryl ethers using arene-manganese chemistry

  摘要：

  Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described. The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schollkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes. Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.

  DOI：

  10.1021/jo00025a026

文献信息

• New cyclic peptides via ring-closing metathesis reactions and their anti-bacterial activities
  作者：Timothy P. Boyle、John B. Bremner、Jonathan Coates、John Deadman、Paul A. Keller、Stephen G. Pyne、David I. Rhodes

  DOI：10.1016/j.tet.2008.09.031

  日期：2008.12

  As part of a program investigating cyclic peptides with an internal aromatic hydrophobic scaffold as potential novel anti-bacterial agents, we explored the synthesis of simple tyrosine-based systems. These were prepared via key intermediates containing internal allylglycine and allyltyrosine residues for subsequent ring-closing metathesis reactions. Although the resulting anti-bacterial activity against

  作为研究带有内部芳香族疏水支架作为潜在新型抗菌剂的环肽的计划的一部分，我们探索了基于酪氨酸的简单系统的合成。这些是通过含有内部烯丙基甘氨酸和烯丙基酪氨酸残基的关键中间体制备的，用于随后的闭环易位反应。尽管所产生的针对金黄色葡萄球菌的抗菌活性适中，但这代表了这类化合物的新颖而简单的途径。一种中间体无环二肽前体显示出对金黄色葡萄球菌的良好活性，MIC为7.8μg/ mL。
• A highly effective phosphinite ligand derived from D-mannitol for Rh-catalyzed asymmetric hydrogenation
  作者：Yixin Chen、Xingshu Li、Siu-kuen Tong、Michael C.K. Choi、Albert S.C. Chan

  DOI：10.1016/s0040-4039(98)02457-5

  日期：1999.1

  chiral phosphinite 1,2,5,6-di-isopropylidene-3,4-bis(diphenylphosphino)-D-mannitol was prepared and its rhodium complex was found to be an effective catalyst for the asymmetric hydrogenation of amidoacrylic acid and its derivatives with product ee's ranging from 90% to 97%.

  制备了一种新型的手性次膦酸酯1,2,5,6-二异亚丙基-3,4-双（二苯基膦基）-D-甘露醇，发现其铑配合物是酰胺基丙烯酸及其不对称加氢的有效催化剂。产品ee介于90％至97％之间的衍生产品。
• Novel Lysophosphatidic Acid Receptor Selective Antagonists
  申请人：Lynch Kevin R.

  公开号：US20080318901A1

  公开（公告）日：2008-12-25

  The present invention is directed to compositions comprising lysophosphatidic acid analogs and methods of using such analogs as agonist or antagonists of LPA receptor activity. In addition the invention is directed to LPA receptor agonists that vary in the degree of selectivity at individual LPA receptors (i.e. LPA1, LPA2 and LPA3). More particularly the present invention is directed to LPA analogs wherein the glycerol is replaced with ethanolamine and a variety of substitutions have been linked at the second carbon atom.

  本发明涉及包含溶血磷脂酸类似物的组合物以及使用这些类似物作为LPA受体活性的激动剂或拮抗剂的方法。此外，本发明涉及在单个LPA受体（即LPA1，LPA2和LPA3）的选择度方面有所不同的LPA受体激动剂。更具体地，本发明涉及LPA类似物，其中甘油被乙醇胺取代，并且在第二个碳原子上连接了各种替代基。
• Peptidic Compounds
  申请人：Boyle Timothy Patrick

  公开号：US20080300287A1

  公开（公告）日：2008-12-04

  The present invention provides a compound of formula (I), (II), (III) and (IV) as defined herein and pharmaceutically acceptable derivatives thereof. The present invention further provides use of the compounds of the present invention in the treatment of bacterial infection and in the treatment of HIV infection. Also provided are pharmaceutical compositions comprising the compounds of the present invention.

  本发明提供了公式（I）、（II）、（III）和（IV）的化合物及其药学上可接受的衍生物。本发明进一步提供了本发明化合物在治疗细菌感染和治疗HIV感染中的用途。还提供了包含本发明化合物的制药组合物。
• PEPTIDIC COMPOUNDS
  申请人：Boyle Timothy Patrick

  公开号：US20110312875A1

  公开（公告）日：2011-12-22

  The present invention provides a compound of formula I, II, III and IV as defined herein and pharmaceutically acceptable derivatives thereof. The present invention further provides use of the compounds of the present invention in the treatment of bacterial infection and in the treatment of HIV infection. Also provided are pharmaceutical compositions comprising the compounds of the present invention.

  本发明提供了公式I、II、III和IV的化合物及其药学上可接受的衍生物。本发明还提供了利用本发明化合物治疗细菌感染和治疗HIV感染的用途。此外，还提供了包含本发明化合物的制药组合物。