(S)-6-chloro-2-methyl-2H-1,4-benzoxazine-3-one | 1448325-19-6

• 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: (S)-6-chloro-2-methyl-2H-1,4-benzoxazine-3-one
• 英文别名: (2S)-6-chloro-2-methyl-4H-1,4-benzoxazin-3-one
• CAS: 1448325-19-6
• 化学式: C₉H₈ClNO₂
• 分子量: 197.621
• InChiKey: MGOCBXKZDZRPMK-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 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

• 作为反应物：
  描述：

  3-氨基吡啶 、 (S)-6-chloro-2-methyl-2H-1,4-benzoxazine-3-one 在 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 4.33h， 以45%的产率得到(S)-6-chloro-2-methyl-3-(pyridin-3-yl-amino)-2H-1,4-benzoxazine
  参考文献：
  名称：

  An efficient synthesis of the optically active isomers of 2H-1,4-benzoxazine derivatives, novel KATP channel modulators

  摘要：

  2H-1,4-Benzoxazine amidine derivatives are drugs acting as modulators of the skeletal muscle and pancreatic beta cell ATP-sensitive-K+ (KATP) channels. With the aim of evaluating the influence of absolute configuration on the biological activity of these drugs, we herein report the optimization of a synthetic route to obtain both enantiomers of some of these compounds with improved chemical yield and high enantiomeric excess. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.027
• 作为产物：
  描述：

  (2S)-2-(4-chloro-2-nitrophenoxy)propanoic acid 在 盐酸 、 铁粉 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 (S)-6-chloro-2-methyl-2H-1,4-benzoxazine-3-one
  参考文献：
  名称：

  An efficient synthesis of the optically active isomers of 2H-1,4-benzoxazine derivatives, novel KATP channel modulators

  摘要：

  2H-1,4-Benzoxazine amidine derivatives are drugs acting as modulators of the skeletal muscle and pancreatic beta cell ATP-sensitive-K+ (KATP) channels. With the aim of evaluating the influence of absolute configuration on the biological activity of these drugs, we herein report the optimization of a synthetic route to obtain both enantiomers of some of these compounds with improved chemical yield and high enantiomeric excess. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.027

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。
• An efficient synthesis of the optically active isomers of 2H-1,4-benzoxazine derivatives, novel KATP channel modulators
  作者：Luca Piemontese、Antonio Laghezza、Giuseppe Fracchiolla、Giuseppe Carbonara、Paolo Tortorella、Fulvio Loiodice

  DOI：10.1016/j.tetasy.2013.05.027

  日期：2013.7

  2H-1,4-Benzoxazine amidine derivatives are drugs acting as modulators of the skeletal muscle and pancreatic beta cell ATP-sensitive-K+ (KATP) channels. With the aim of evaluating the influence of absolute configuration on the biological activity of these drugs, we herein report the optimization of a synthetic route to obtain both enantiomers of some of these compounds with improved chemical yield and high enantiomeric excess. (C) 2013 Elsevier Ltd. All rights reserved.