1-[6-Bromo-1-(4-methylphenyl)sulfonyl-2,4-dihydro-3,1-benzoxazin-2-yl]propan-2-one | 1210801-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[6-Bromo-1-(4-methylphenyl)sulfonyl-2,4-dihydro-3,1-benzoxazin-2-yl]propan-2-one
• CAS: 1210801-66-3
• 化学式: C₁₈H₁₈BrNO₄S
• 分子量: 424.315
• InChiKey: KPHYJCYQOQTWMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-溴-2-(羟甲基)苯基)-4-甲基苯磺酰胺 、 3-丁炔-2-酮 在 1,3-双(二苯基膦)丙烷 、 sodium acetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以88%的产率得到1-[6-Bromo-1-(4-methylphenyl)sulfonyl-2,4-dihydro-3,1-benzoxazin-2-yl]propan-2-one
  参考文献：
  名称：

  Diphosphine-Catalyzed Mixed Double-Michael Reaction: A Unified Synthesis of Indolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1-oxazines

  摘要：

  Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.

  DOI：

  10.1021/ol100078w

文献信息

• Diphosphine-Catalyzed Mixed Double-Michael Reaction: A Unified Synthesis of Indolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1-oxazines
  作者：Vardhineedi Sriramurthy、Ohyun Kwon

  DOI：10.1021/ol100078w

  日期：2010.3.5

  Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.