5,6-dihydro-3,5-dimethyl-5-(hydroxymethyl)-2H-1,4-oxazin-2-one | 108713-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪类
• 英文名称: 5,6-dihydro-3,5-dimethyl-5-(hydroxymethyl)-2H-1,4-oxazin-2-one
• 英文别名: 5,6-Dihydro-3,5-dimethyl-5-hydroxymethyl-1,4-oxazin-2-one；3-(hydroxymethyl)-3,5-dimethyl-2H-1,4-oxazin-6-one
• CAS: 108713-77-5
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: NHKVDXITOHNGJF-UHFFFAOYSA-N

物化性质

• 沸点：
  246.6±32.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-3,5-dimethyl-5-(hydroxymethyl)-2H-1,4-oxazin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 3,5-dimethyl-5-(hydroxymethyl)-2-oxomorpholine
  参考文献：
  名称：

  Bi[3,5-dimethyl-5-(hydroxymethyl)-2-oxomorpholin-3-yl] (DHM-3 dimer). A water-soluble, one-electron reducing agent

  摘要：

  DOI：

  10.1021/jo00390a020
• 作为产物：
  描述：

  5-(羟甲基)-3-[5-(羟甲基)-3,5-二甲基-2-氧代吗啉-3-基]-3,5-二甲基吗啉-2-酮 在 氧气 作用下， 以 乙腈 为溶剂， 生成 5,6-dihydro-3,5-dimethyl-5-(hydroxymethyl)-2H-1,4-oxazin-2-one
  参考文献：
  名称：

  Bi[3,5-dimethyl-5-(hydroxymethyl)-2-oxomorpholin-3-yl] (DHM-3 dimer). A water-soluble, one-electron reducing agent

  摘要：

  DOI：

  10.1021/jo00390a020

文献信息

• Oxomorpholinyl dimer and rescue of anthracycline and mitomycin C damage
  申请人：The United States of America as represented by the Department of Health

  公开号：US04632922A1

  公开（公告）日：1986-12-30

  The present invention discloses a bi(3,5-dimethyl-5-hydroxymethyl-2-oxomorpholin-3-yl) compound and its efficacy as a rescue agent against anthracycline and mitomycin C induced tissue damage. A method of synthesizing said compound has also been described.

  本发明公开了一种bi(3,5-二甲基-5-羟甲基-2-氧代嘧啶-3-基)化合物及其作为对抗蒽环类和丝裂霉素C引起的组织损伤的救治剂的功效。同时也描述了一种合成该化合物的方法。
• Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer). A low toxicity, water-soluble, one-electron reducing agent
  作者：Giorgio Gaudiano、Elizabeth Frank、Michael S. Wysor、Steven D. Averbuch、Tad H. Koch

  DOI：10.1021/jo00078a011

  日期：1993.12

  Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer) was synthesized by condensing tris(hydroxymethyl)aminomethane with ethyl pyruvate to form 5,6-dihydro-5,5-bis-(hydroxymethyl)-3-methyl-1,4-oxazin-2-one (1) followed by photoreduction in 2-propanol. BHM-3 dimer exists in equilibrium with 5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl (BHM-3) in solution; the rate constant for BHM-3 formation from dimers varies with solvent increasing from 5.3 x 10(-6) s-1 in acetonitrile to 1.5 x 10(-3) s-1 in water at 25-degrees-C. BHM-3 reacts as a one-electron reducing agent, and the reduction potential for BHM-3 dimer is estimated at -0.54 V vs NHE from the position of equilibrium for the reduction of the viologen, propyldiquat, to its radical cation. BHM-3 dimer has an octanol/water partition coefficient of 0.054 and shows low mouse toxicity even upon intravenous administration. Intravenously administered BHM-3 dimer projects mice from an immediated subsequent lethal injection of the antitumor drug adriamycin. The properties of BHM-3 dimer are compared with those of other 2-oxomorpholin-3-yl dimers.
• GAUDIANO, G.;KOCH, T. H., J. ORG. CHEM., 52,(1987) N 14, 3073-3081
  作者：GAUDIANO, G.、KOCH, T. H.

  DOI：——

  日期：——
• US4632922A
  申请人：——

  公开号：US4632922A

  公开（公告）日：1986-12-30