3,5,5-trimethyl-2-oxomorpholin-3-yl | 57765-64-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 原羧酸衍生物
• 英文名称: 3,5,5-trimethyl-2-oxomorpholin-3-yl
• 英文别名: 3,5,5-trimethyl-2-oxomorpholin-3-yl radical
• CAS: 57765-64-7
• 化学式: C₇H₁₂NO₂
• 分子量: 142.178
• InChiKey: KBSSDOHVHZAMRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5,5-trimethyl-2-oxomorpholin-3-yl 在 氧气 作用下， 以 氯仿 为溶剂， 以95%的产率得到5,6-dihydro-3,5,5-trimethyl-1,4-oxazin-2-one
  参考文献：
  名称：

  Oxidation of 3,5,5-trimethyl-2-oxomorpholin-3-yl (TM-3) with molecular oxygen. Generation of a persistent aminyl radical

  摘要：

  DOI：

  10.1021/ja00276a056
• 作为产物：
  描述：

  3,5,5-三甲基-2-吗啉酮 在 tert-butoxyl radical 作用下， 以 苯 为溶剂， 生成 3,5,5-trimethyl-2-oxomorpholin-3-yl
  参考文献：
  名称：

  Clark, K. Brady; Wayner, Danial D. M.; Demirdji, Samuel H., Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2447 - 2453

  摘要：

  DOI：
• 作为试剂：
  描述：

  道诺霉素 在 三羟甲基氨基甲烷盐酸盐 、 3,5,5-trimethyl-2-oxomorpholin-3-yl 、 三羟甲基氨基甲烷 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 生成 7-deoxydaunomycinone hydroquinone
  参考文献：
  名称：

  Mechanistic investigation of reduction of daunomycin and 7-deoxydaunomycinone with bi(3,5,5-trimethyl-2-oxomorpholin-3-yl)

  摘要：

  DOI：

  10.1021/ja00320a027

文献信息

• Reduction of daunomycin in dimethyl sulfoxide. Long-lived semiquinones and quinone methide and formation of an enolate at the 14-position via the quinone methide.
  作者：Giorgio Gaudiano、Massimo Frigerio、Pierfrancesco Bravo、Tad H. Koch

  DOI：10.1021/ja00034a054

  日期：1992.4

  Anaerobic reduction of daunomycin (1, daunorubicin) in 5%/95% H 2 O/DMSO (DMSO=dimethyl sulfoxide) or in DMSO with sodium dithionite or bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer), respectively, yields 7-deoxydaunomycinone (7) and a mixture of the diastereomers of bi(7-deoxydaunomycinon-7-yl) (8). A precursor to both 7 and 8 is 7-deoxydaunomycinone quinone methide (4) formed from glycosidic

  在 5%/95% H 2 O/DMSO（DMSO=二甲基亚砜）或 DMSO 中用连二亚硫酸钠或双 (3,5,5-trimethyl-2-oxomorpholin-3-yl) 厌氧还原柔红霉素（1，柔红霉素） ) (TM-3 二聚体) 分别产生 7-脱氧道诺霉素酮 (7) 和双(7-脱氧道诺霉素-7-基) (8) 的非对映异构体的混合物。7 和 8 的前体是 7-脱氧道诺霉素醌甲基化物 (4)，由道诺霉素氢醌 (3) 的糖苷裂解形成。对苯二酚 3 从相对速率确定为醌甲基化物 4 的前体
• Equilibrium between 2-oxomorpholin-3-yl radicals and viologen radicals. Determination of reduction potentials
  作者：Robert Patrick Mahoney、Paul A. Fretwell、Samuel H. Demirdji、R. L. Mauldin、Olester Benson、Tad H. Koch

  DOI：10.1021/ja00027a026

  日期：1992.1

  Bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer) undergoes bond homolysis to yield 3,5,5-trimethyl-2-oxomorpholin-3-yl (TM-3), which reduces propyldiquat (PDQ2+) to its radical cation PDQ+. The byproduct is 5,6-dihydro-3, 5,5-trimethyl-1,4-oxazin-2-one (8). Similarly, bi(5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl) (DEM-3 dimer) cleaves to 5,5-dimethyl-4-ethyl-2-oxomorpholin-3-yl (DEM-3), which reduces paraquat (PQ2+) to its radical cation PQ+. The byproduct, 5,5-dimethyl-4-ethyl-3-methoxy-2-oxomorpholine (10), results from rapid addition of methanol solvent to the transient 5,6-dihydro-4-ethyl-5, 5-dimethyl-1,4-oxazin-2-onium cation (11). Concentration versus time data for the respective viologen radical cations together with reduction potentials for the viologens place the reduction potentials for TM-3 dimer and DEM-3 dimer at -0.56 and -0.33 V versus NHE, respectively, in Tris/Tris-H+ buffered methanol. The kinetics of reduction are analyzed using numerical integration, and the two reducing agents are compared with dithionite.
• Electron-transfer chemistry of the merostabilized 3,5,5-trimethyl-2-morpholinon-3-yl radical
  作者：John M. Burns、Donald L. Wharry、Tad H. Koch

  DOI：10.1021/ja00394a020

  日期：1981.2
• Formation and reaction of the quinone methide from reductive cleavage of the antitumor drug menogaril
  作者：Marybeth Boldt、Giorgio Gaudiano、Makhluf J. Haddadin、Tad H. Koch

  DOI：10.1021/ja00188a050

  日期：1989.3
• Formation kinetics of an amino carboxy type merostabilized free radical
  作者：Richard W. Bennett、Donald L. Wharry、Tad H. Koch

  DOI：10.1021/ja00527a036

  日期：1980.3