(Z)-4-acetyl-3-[(4-methylphenyl)methylidene]-3,4-dihydro-2H-1,4-benzoxazine | 849064-98-8

• 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: (Z)-4-acetyl-3-[(4-methylphenyl)methylidene]-3,4-dihydro-2H-1,4-benzoxazine
• 英文别名: 1-[(3Z)-3-[(4-methylphenyl)methylidene]-1,4-benzoxazin-4-yl]ethanone
• CAS: 849064-98-8
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: LCDSGWIIUCBRJM-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-acetyl-3-[(4-methylphenyl)methylidene]-3,4-dihydro-2H-1,4-benzoxazine 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 (-)-1,2-双[(2R,5R)-2,5-二甲基磷]苯 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、413.68 kPa 条件下， 反应 16.0h， 以96%的产率得到(R)-3-[(4-methylphenyl)methyl]-4-acetyl-3,4-dihydro-2H-1,4-benzoxazine
  参考文献：
  名称：

  Synthesis and Highly Enantioselective Hydrogenation of Exocyclic Enamides:  (Z)-3-Arylidene-4-acetyl-3,4-dihydro-2H- 1,4-benzoxazines

  摘要：

  Highly enantioselective hydrogenation of exocyclic enamides, (Z)-3-arylidene-4-acyl-3,4-dihydro-2H-benzoxazines, was achieved in up to 98.6% ee by using Rh/(R,R)-Me-Duphos complex as the catalytic system. The absolute configuration of the product was assigned as R by chemical interrelations.

  DOI：

  10.1021/jo048212s
• 作为产物：
  描述：

  2-丙炔-2-氧基-苯基amine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 吡啶 、 copper(l) iodide 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 (Z)-4-acetyl-3-[(4-methylphenyl)methylidene]-3,4-dihydro-2H-1,4-benzoxazine
  参考文献：
  名称：

  Synthesis and Highly Enantioselective Hydrogenation of Exocyclic Enamides:  (Z)-3-Arylidene-4-acetyl-3,4-dihydro-2H- 1,4-benzoxazines

  摘要：

  Highly enantioselective hydrogenation of exocyclic enamides, (Z)-3-arylidene-4-acyl-3,4-dihydro-2H-benzoxazines, was achieved in up to 98.6% ee by using Rh/(R,R)-Me-Duphos complex as the catalytic system. The absolute configuration of the product was assigned as R by chemical interrelations.

  DOI：

  10.1021/jo048212s

文献信息

• Synthesis and Highly Enantioselective Hydrogenation of Exocyclic Enamides:  (<i>Z</i>)-3-Arylidene-4-acetyl-3,4-dihydro-2<i>H</i>- 1,4-benzoxazines
  作者：Yong-Gui Zhou、Peng-Yu Yang、Xiu-Wen Han

  DOI：10.1021/jo048212s

  日期：2005.3.1

  Highly enantioselective hydrogenation of exocyclic enamides, (Z)-3-arylidene-4-acyl-3,4-dihydro-2H-benzoxazines, was achieved in up to 98.6% ee by using Rh/(R,R)-Me-Duphos complex as the catalytic system. The absolute configuration of the product was assigned as R by chemical interrelations.