4-methyl-2H-benzo[b][1,4]oxazine-2,3(4H)-dione | 72985-52-5

• 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-methyl-2H-benzo[b][1,4]oxazine-2,3(4H)-dione
• 英文别名: 4-Methyl-4H-benzo[1,4]oxazine-2,3-dione；4-Methyl-1,4-benzoxazine-2,3-dione
• CAS: 72985-52-5
• 化学式: C₉H₇NO₃
• 分子量: 177.159
• InChiKey: OCTALGFQZRBHBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-2H-benzo[b][1,4]oxazine-2,3(4H)-dione 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 19.0h， 生成 4-methyl-3-oxo-2-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl 2,2-diphenylacetate
  参考文献：
  名称：

  10.1002/anie.202402908

  摘要：

  The development of methods to allow the selective acylative dynamic kinetic resolution (DKR) of tetra‐substituted lactols is a recognised synthetic challenge. In this manuscript, a highly enantioselective isothiourea‐catalysed acylative DKR of tetra‐substituted morpholinone and benzoxazinone‐derived lactols is reported. The scope and limitations of this methodology have been developed, with high enantioselectivity and good to excellent yields (up to 89%, 99:1 er) observed across a broad range of substrate derivatives incorporating substitution at N(4) and C(2), di‐ and spirocyclic substitution at C(5)‐ and C(6)‐position, as well as benzannulation (>35 examples in total). The DKR process is amenable to scale‐up on a 1 g laboratory scale. The factors leading to high selectivity in this DKR process have been probed through computation, with an N‐C=O•••isothiouronium interaction identified as key to producing ester products in highly enantioenriched form.

  DOI：

  10.1002/anie.202402908
• 作为产物：
  描述：

  草酰氯 、 2-甲氨基苯酚 在 三乙胺 作用下， 以 甲苯 为溶剂， 以93 %的产率得到4-methyl-2H-benzo[b][1,4]oxazine-2,3(4H)-dione
  参考文献：
  名称：

  10.1002/anie.202402908

  摘要：

  The development of methods to allow the selective acylative dynamic kinetic resolution (DKR) of tetra‐substituted lactols is a recognised synthetic challenge. In this manuscript, a highly enantioselective isothiourea‐catalysed acylative DKR of tetra‐substituted morpholinone and benzoxazinone‐derived lactols is reported. The scope and limitations of this methodology have been developed, with high enantioselectivity and good to excellent yields (up to 89%, 99:1 er) observed across a broad range of substrate derivatives incorporating substitution at N(4) and C(2), di‐ and spirocyclic substitution at C(5)‐ and C(6)‐position, as well as benzannulation (>35 examples in total). The DKR process is amenable to scale‐up on a 1 g laboratory scale. The factors leading to high selectivity in this DKR process have been probed through computation, with an N‐C=O•••isothiouronium interaction identified as key to producing ester products in highly enantioenriched form.

  DOI：

  10.1002/anie.202402908

文献信息

• LOEV, B.;JONES, H.;BROWN, R. E.;HUANG, FU-CHIH;KHANDWALA, A.;LEIBOWITZ, M+, J. MED. CHEM., 1985, 28, N 1, 24-27
  作者：LOEV, B.、JONES, H.、BROWN, R. E.、HUANG, FU-CHIH、KHANDWALA, A.、LEIBOWITZ, M+

  DOI：——

  日期：——