5,6-Dihydro-5,5-bis(hydroxymethyl)-3-methyl-1,4-oxazin-2-one | 86528-00-9

• 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-5,5-bis(hydroxymethyl)-3-methyl-1,4-oxazin-2-one
• 英文别名: 3,3-bis(hydroxymethyl)-5-methyl-2H-1,4-oxazin-6-one
• CAS: 86528-00-9
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: RFQFTHBUFCKSBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-Dihydro-5,5-bis(hydroxymethyl)-3-methyl-1,4-oxazin-2-one 在 异丙醇 作用下， 以 乙酸乙酯 为溶剂， 反应 55.0h， 以25%的产率得到Bi(5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl)
  参考文献：
  名称：

  Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer). A low toxicity, water-soluble, one-electron reducing agent

  摘要：

  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.

  DOI：

  10.1021/jo00078a011
• 作为产物：
  描述：

  5,5-Bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl 在 三羟甲基氨基甲烷盐酸盐 、 三羟甲基氨基甲烷 、 paraquat 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 5,6-Dihydro-5,5-bis(hydroxymethyl)-3-methyl-1,4-oxazin-2-one
  参考文献：
  名称：

  Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer). A low toxicity, water-soluble, one-electron reducing agent

  摘要：

  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.

  DOI：

  10.1021/jo00078a011

文献信息

• Substituent effects on the formation of aminocarboxy-type capto-dative free radicals
  作者：Richard J. Himmelsbach、Anthony D. Barone、Don L. Kleyer、Tad H. Koch

  DOI：10.1021/jo00166a010

  日期：1983.9
• 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.