methyl (R)-2-(2-nitrophenoxy)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (R)-2-(2-nitrophenoxy)propanoate
• 英文别名: methyl (2R)-2-(2-nitrophenoxy)propanoate
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: QOTCLHMAHIPHPL-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-2-(2-nitrophenoxy)propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(R)-2-(2-nitrophenoxy)propanoic acid
  参考文献：
  名称：

  含光团乳糖醇衍生物的不对称合成阐明甜味受体

  摘要：

  Lactisole 具有 2-苯氧基丙酸骨架，是众所周知的甜味受体抑制剂。我们最近揭示了乳糖醇的芳香环和手性中心的一些构效关系。光亲和标记是阐明生物活性化合物与生物分子之间相互作用的常用化学生物学方法之一。在本文中，描述了用于光亲和标记的具有常见光团（二苯甲酮、叠氮化物和三氟甲基二氮嗪）的乳糖醇衍生物的新型不对称合成。合成的化合物受到基于细胞的甜味受体的影响，用三氟甲基二氮杂环发光团取代对合成化合物受体的亲和力最高。

  DOI：

  10.3390/molecules25122790
• 作为产物：
  描述：

  L-乳酸甲酯 、 硝苯酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以84%的产率得到methyl (R)-2-(2-nitrophenoxy)propanoate
  参考文献：
  名称：

  Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer

  摘要：

  Peptidomimetic foldamers were synthesized by oligomerizing derivatives of the delta-amino acid analogue, 2-(2-aminophenoxy)alkanoic acid. Single-crystal analysis of the tetramer reveals a 2(1)-helical secondary structure stabilized by hydrogen bonding and the coiled stacking of aromatic rings. The M-helicity of 2-aminoplienoxyacetic acid oligomers was induced by the incorporation of only a single chiral carbon of the N-terminal (R)-2-(2-nitrophenoxy)propionamide moiety. The solution state CD spectra demonstrated that the resulting helix induced a substantial Cotton effect. The secondary structure was further characterized by IR and NMR spectroscopy. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.003

文献信息

• Induced helix of 2-(2-aminophenoxy)alkanoic acid oligomers as a δ-peptidomimetic foldamer
  作者：Motohiro Akazome、Yuichi Ishii、Tatsuya Nireki、Katsuyuki Ogura

  DOI：10.1016/j.tetlet.2008.05.003

  日期：2008.7

  Peptidomimetic foldamers were synthesized by oligomerizing derivatives of the delta-amino acid analogue, 2-(2-aminophenoxy)alkanoic acid. Single-crystal analysis of the tetramer reveals a 2(1)-helical secondary structure stabilized by hydrogen bonding and the coiled stacking of aromatic rings. The M-helicity of 2-aminoplienoxyacetic acid oligomers was induced by the incorporation of only a single chiral carbon of the N-terminal (R)-2-(2-nitrophenoxy)propionamide moiety. The solution state CD spectra demonstrated that the resulting helix induced a substantial Cotton effect. The secondary structure was further characterized by IR and NMR spectroscopy. (c) 2008 Elsevier Ltd. All rights reserved.
• Azzolina; Collina; Ghislandi, Il Farmaco, 1993, vol. 48, # 10, p. 1401 - 1416
  作者：Azzolina、Collina、Ghislandi

  DOI：——

  日期：——
• Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors
  作者：Tomoya Nakagita、Akiko Ishida、Zetryana Puteri Tachrim、Lei Wang、Takumi Misaka、Makoto Hashimoto

  DOI：10.3390/molecules25122790

  日期：——

  We recently revealed some of the structure–activity relationships of the aromatic ring and chiral center of lactisole. Photoaffinity labeling is one of the common chemical biology methods to elucidate the interaction between bioactive compounds and biomolecules. In this paper, the novel asymmetric synthesis of lactisole derivatives with common photophores (benzophenone, azide and trifluoromethyldiazirine)

  Lactisole 具有 2-苯氧基丙酸骨架，是众所周知的甜味受体抑制剂。我们最近揭示了乳糖醇的芳香环和手性中心的一些构效关系。光亲和标记是阐明生物活性化合物与生物分子之间相互作用的常用化学生物学方法之一。在本文中，描述了用于光亲和标记的具有常见光团（二苯甲酮、叠氮化物和三氟甲基二氮嗪）的乳糖醇衍生物的新型不对称合成。合成的化合物受到基于细胞的甜味受体的影响，用三氟甲基二氮杂环发光团取代对合成化合物受体的亲和力最高。
• A cyclic trimer of 2-(2-aminophenoxy)propionic acid with a bowl-shaped structure
  作者：Motohiro Akazome、Junpei Sukegawa、Yohei Goto、Shoji Matsumoto

  DOI：10.1016/j.tetlet.2009.07.029

  日期：2009.9

  A cyclic trimer of (R)-2-(2-aminophenoxy)propanoic acid, a delta-amino acid analogue, was synthesized. Molecular mechanics calculations on the cyclic trimer predicted that a concave network of sequential hydrogen bonds forms a C(3)-symmetric bowl-shaped structure. Evidence for this conformation was found in the NMR spectra of the trimer in D-chloroform. Although the single-crystal structure of the cyclic trimer indicates that chloroform could be included in the bowl-shaped structure, the conformation was not C(3)-symmetric and the hydrogen bonding network was of a different mode. These different conformations between solid and Solution were reasonably clear from IR spectra. (C) 2009 Elsevier Ltd. All Fights reserved.