2-(3-chloropropyl)-2-phenyl-2H-1,4-benzoxazin-3(4H)-one | 871976-44-2

• 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: 2-(3-chloropropyl)-2-phenyl-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: 2-(3-chloropropyl)-2-phenyl-4H-1,4-benzoxazin-3-one
• CAS: 871976-44-2
• 化学式: C₁₇H₁₆ClNO₂
• 分子量: 301.773
• InChiKey: SVSAGQOHCPLUHW-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C(Solvent: Hexane; Diethyl ether)
• 沸点：
  493.0±45.0 °C(predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  2-(3-chloropropyl)-2-phenyl-2H-1,4-benzoxazin-3(4H)-one 、 乙酸乙酯 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以49%的产率得到2-(3-hydroxypropyl)-2-phenyl-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  叠氮基稠合中等尺寸杂环中的新型环过反应：叠氮基[2,1-e] [1,6]苯并恶唑啉和-苯并噻唑啉选择性转化为氧杂（thia）zine和氧杂（thia）zole衍生物

  摘要：

  Opening of the three-membered ring in heterocyclic systems incorporating a dichloroaziridine ring fused to eight-membered O,N-or S,N-heterocycles is accompanied by transannular reactions with participation of the endocyclic oxygen and sulfur atoms. Depending on the conditions, the products are 1,4-benzoxazine (1,4-benzothiazine) or 1,3-benzoxazole (1,3-benzothiazole) derivatives. The discovered transformations were used as a basis of methods for the preparation of new heterocyclic systems, 2,3,4,4a-tetrahydro-1H-pyrido-[3,2-b][1,4]benzoxa(thia)zine derivatives, in domino or consecutive modes, as well as of pyrrolidinyl-substituted 1,3-benzoxa(thia)zoles.

  DOI：

  10.1134/s1070428007070214
• 作为产物：
  描述：

  1-chloro-1-fluoro-1a-phenyl-1a,2,3,4-tetrahydro-1H-azirino[2,1-e][1,6]benzoxazocine 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到2-(3-chloropropyl)-2-phenyl-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  叠氮基稠合的八元O，N-或S，N-杂环中的选择性跨环转移。

  摘要：

  描述了在氮丙啶稠合的八元O，N或S，N-杂环中涉及选择性氮丙啶开环和中型环收缩的跨环转移的第一个例子，提供了官能化1,4-苯并（噻嗪类或1,3-苯并（噻吩）唑类。

  DOI：

  10.1039/b512409c

文献信息

• Selective transannular ring transformations in azirino-fused eight-membered O,N- or S,N-heterocycles
  作者：Alexander F. Khlebnikov、Mikhail S. Novikov、Ekaterina Yu. Shinkevich、Denis Vidovic

  DOI：10.1039/b512409c

  日期：——

  The first examples of transannular ring transformations in azirino-fused eight-membered O,N- or S,N-heterocycles involving selective aziridine ring opening and medium-sized ring contraction are described, which provide an access to functionalized 1,4-benzox(thi)azines or 1,3-benzox(thi)azoles.

  描述了在氮丙啶稠合的八元O，N或S，N-杂环中涉及选择性氮丙啶开环和中型环收缩的跨环转移的第一个例子，提供了官能化1,4-苯并（噻嗪类或1,3-苯并（噻吩）唑类。
• New type of transannular reactions in azirine-fused medium-size heterocycles: Selective transformations of azirino[2,1-e][1,6]benzoxazocines and -benzothiazocines into oxa(thia)zine and oxa(thia)zole derivatives
  作者：E. Yu. Shinkevich、M. S. Novikov、A. F. Khlebnikov、R. R. Kostikov、J. Kopf、J. Magull

  DOI：10.1134/s1070428007070214

  日期：2007.7

  Opening of the three-membered ring in heterocyclic systems incorporating a dichloroaziridine ring fused to eight-membered O,N-or S,N-heterocycles is accompanied by transannular reactions with participation of the endocyclic oxygen and sulfur atoms. Depending on the conditions, the products are 1,4-benzoxazine (1,4-benzothiazine) or 1,3-benzoxazole (1,3-benzothiazole) derivatives. The discovered transformations were used as a basis of methods for the preparation of new heterocyclic systems, 2,3,4,4a-tetrahydro-1H-pyrido-[3,2-b][1,4]benzoxa(thia)zine derivatives, in domino or consecutive modes, as well as of pyrrolidinyl-substituted 1,3-benzoxa(thia)zoles.