4-(trifluoromethyl)-2-morpholino-4-phenyl-4H-3,1-benzoxazine | 1160653-36-0

• 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: 4-(trifluoromethyl)-2-morpholino-4-phenyl-4H-3,1-benzoxazine
• 英文别名: 2-Morpholin-4-yl-4-phenyl-4-(trifluoromethyl)-3,1-benzoxazine
• CAS: 1160653-36-0
• 化学式: C₁₉H₁₇F₃N₂O₂
• 分子量: 362.351
• InChiKey: LBLAKXRNLBNQHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吗啉 、 2,2,2-三氟苯乙酮 、 1-溴-2-异氰基苯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 以55%的产率得到4-(trifluoromethyl)-2-morpholino-4-phenyl-4H-3,1-benzoxazine
  参考文献：
  名称：

  Reactions of ortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines

  摘要：

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).

  DOI：

  10.1021/jo9004734

文献信息

• Reactions of <i>ortho</i>-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4<i>H</i>-3,1-Benzoxazines
  作者：Alexander V. Lygin、Armin de Meijere

  DOI：10.1021/jo9004734

  日期：2009.6.19

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).