2-tert-butyl-4-phenyl-4H-3,1-benzoxazine | 28586-62-1

• 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-tert-butyl-4-phenyl-4H-3,1-benzoxazine
• 英文别名: 2-tert-butyl-4-phenyl-4H-benzo[d][1,3]oxazine
• CAS: 28586-62-1
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: GEKCMSWRYIYCTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[2-[hydroxy(phenyl)methyl]phenyl]-2,2-dimethylpropanamide 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以53%的产率得到2-tert-butyl-4-phenyl-4H-3,1-benzoxazine
  参考文献：
  名称：

  Synthesis of 4H-3,1-Benzoxazines by the Reaction of o-(N-Acylamino)benzyl Alcohols with DAST

  摘要：

  The treatment of o-(N-acylamino)benzyl alcohols (1) with DAST afforded the dehydrative cyclization product, 4H-3,1-benzoxazines (4) and the hydroxy replacement product, o-(N-acylamino)benzyl fluorides (5). The yields of benzoxazines (4) and fluorides (5) depend on the substituents at alpha-position and acyl groups. The treatment of alpha,alpha-diaryl-o-(N-acylamino)benzyl alcohols (1a-c) with DAST yielded benzoxazines (4a-c) exclusively, while that of alpha-monosubstituted o-(N-acylamino)benzyl alcohols (Id-k) with DAST yielded benzoxazines (4d-k) and fluorides (5d-k). In the reaction of o-(N-acylamino)benzyl alcohol (11) with DAST, the formation of fluoride (51) became predominant and that of benzoxazine (41) was suppressed almost completely.

  DOI：

  10.3987/com-05-s(t)22

文献信息

• Synthesis of 4H-3,1-Benzoxazines by the Reaction of o-(N-Acylamino)benzyl Alcohols with DAST
  作者：Takehiko Nishio、Yukiko Kurokawa、Yoshiya Narasaki、Tatsuhiro Tokunaga

  DOI：10.3987/com-05-s(t)22

  日期：——

  The treatment of o-(N-acylamino)benzyl alcohols (1) with DAST afforded the dehydrative cyclization product, 4H-3,1-benzoxazines (4) and the hydroxy replacement product, o-(N-acylamino)benzyl fluorides (5). The yields of benzoxazines (4) and fluorides (5) depend on the substituents at alpha-position and acyl groups. The treatment of alpha,alpha-diaryl-o-(N-acylamino)benzyl alcohols (1a-c) with DAST yielded benzoxazines (4a-c) exclusively, while that of alpha-monosubstituted o-(N-acylamino)benzyl alcohols (Id-k) with DAST yielded benzoxazines (4d-k) and fluorides (5d-k). In the reaction of o-(N-acylamino)benzyl alcohol (11) with DAST, the formation of fluoride (51) became predominant and that of benzoxazine (41) was suppressed almost completely.