2,3-dihydro-[1,4]oxazine-4-carbaldehyde | 61157-72-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-dihydro-[1,4]oxazine-4-carbaldehyde
• 英文别名: 2,3-didehydromorpholine-4-carbaldehyde；N-formyl-2,3-dihydro-4H-1,4-oxazine；2,3-dehydro-N-formylmorpholine；4-formyl-3,4-dihydro-2H-[1,4]oxazine；N-Formyl-dehydromorpholin；2,3-dihydro-1,4-oxazine-4-carbaldehyde
• CAS: 61157-72-0
• 化学式: C₅H₇NO₂
• 分子量: 113.116
• InChiKey: WRBGTFLHDVXZKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2,3-dihydro-[1,4]oxazine-4-carbaldehyde 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以79%的产率得到4-methyl-3,4-dihydro-2H-[1,4]oxazine
  参考文献：
  名称：

  Confirmation by trapping, synthesis, and reactivity of 2,3-dehydro-N-methylmorpholine (DNMM)

  摘要：

  The elusive 4-methyl-3,4-dihydro-2H-[1,4] oxazine (2,3-dehydro-N-methylmorpholine, DNMM, 5) was confirmed to occur as degradation product of N-methylmorpholine-N-oxide (1) by trapping with the alpha-tocopherol-derived ortho-quinone methide in a hetero-Diels-Alder reaction with inverse electron demand. The regioselectivity of the addition was in good agreement with DFT computational data. An authentic sample of 5 was synthesized from formmorpholide (16) via 2-methoxy-formmorpholide in 38% overall yield. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.09.055
• 作为产物：
  描述：

  4-甲氧基-3-甲氧基吗啉 在 三氟甲磺酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以92%的产率得到2,3-dihydro-[1,4]oxazine-4-carbaldehyde
  参考文献：
  名称：

  Confirmation by trapping, synthesis, and reactivity of 2,3-dehydro-N-methylmorpholine (DNMM)

  摘要：

  The elusive 4-methyl-3,4-dihydro-2H-[1,4] oxazine (2,3-dehydro-N-methylmorpholine, DNMM, 5) was confirmed to occur as degradation product of N-methylmorpholine-N-oxide (1) by trapping with the alpha-tocopherol-derived ortho-quinone methide in a hetero-Diels-Alder reaction with inverse electron demand. The regioselectivity of the addition was in good agreement with DFT computational data. An authentic sample of 5 was synthesized from formmorpholide (16) via 2-methoxy-formmorpholide in 38% overall yield. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.09.055

文献信息

• Palasz, Peter D.; Utley, James H. P.; Hardstone, J. David, Journal of the Chemical Society. Perkin transactions II, 1984, # 4, p. 807 - 814
  作者：Palasz, Peter D.、Utley, James H. P.、Hardstone, J. David

  DOI：——

  日期：——
• Eberson, Lennart; Malmberg, Mats; Nyberg, Klas, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 5, p. 345 - 350
  作者：Eberson, Lennart、Malmberg, Mats、Nyberg, Klas

  DOI：——

  日期：——
• Synthesis of Cyclic<i>N</i>-Acylenamines
  作者：Klas NYBERG

  DOI：10.1055/s-1976-24118

  日期：——
• Eberson, Lennart; Malmberg, Mats; Nyberg, Klas, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 5, p. 391 - 396
  作者：Eberson, Lennart、Malmberg, Mats、Nyberg, Klas

  DOI：——

  日期：——
• PALASZ, P. D.;UTLEY, J. H. P.;HARDSTONE, J. D., J. CHEM. SOC. PERKIN TRANS., 1984, N 4, 807-813
  作者：PALASZ, P. D.、UTLEY, J. H. P.、HARDSTONE, J. D.

  DOI：——

  日期：——