(R)-2-methyl-(2H)-1,4-benzoxazin-3(4H)-one | 1186579-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: (R)-2-methyl-(2H)-1,4-benzoxazin-3(4H)-one
• 英文别名: (2R)-2-methyl-4H-1,4-benzoxazin-3-one
• CAS: 1186579-98-5
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: PILVMCZSXIINLV-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (R)-2-(2-nitrophenoxy)propanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以97%的产率得到(R)-2-methyl-(2H)-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  A cyclic trimer of 2-(2-aminophenoxy)propionic acid with a bowl-shaped structure

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.07.029

文献信息

• A facile route for highly enantioenriched six‐membered 1,4‐<i>N,N</i>‐ and <i>N,O</i>‐heterocycles from <scp>L</scp>‐serinate‐derived <scp>α</scp>‐bromoacetates
  作者：So Jeong Lee、Min Ji Park、Seyeon Kim、Yong Sun Park

  DOI：10.1002/bkcs.12787

  日期：2023.12

  Preparation of highly enantioenriched six-membered 1,4-N,N- and N,O-heterocycles has been developed through [4 + 2] heteroannulation of α-bromoacetates with 1,4-binucleophiles. Two consecutive substitutions of highly diastereoenriched L-serinate-derived α-bromoacetates provide convenient access to a wide range of C-aryl/aliphatic substituted 1,4-N,N- and N,O-heterocycles with up to 99:1 er.

  通过 α-溴乙酸酯与 1,4-双亲核试剂的 [4 + 2] 杂环化，开发了高度对映体富集的六元 1,4- N,N-和N,O-杂环。高度非对映体富集的 L-丝氨酸衍生的 α-溴乙酸酯的两次连续取代可方便地获得各种 C-芳基/脂肪族取代的 1,4- N,N-和N,O-杂环，其比例高达 99:1。
• 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.