(R)-2-tert-butyl-3-methyl-2,3-dihydroimidazol-4-one N-oxide | 699432-58-1

• 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: (R)-2-tert-butyl-3-methyl-2,3-dihydroimidazol-4-one N-oxide
• 英文别名: (2S)-2-tert-butyl-3-methyl-1-oxido-2H-imidazol-1-ium-4-one
• CAS: 699432-58-1
• 化学式: C₈H₁₄N₂O₂
• 分子量: 170.211
• InChiKey: LTWORCIGJSZNEQ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-tert-butyl-3-methyl-2,3-dihydroimidazol-4-one N-oxide 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 76.0h， 生成 (2R,5S,2'S)-2-tert-butyl-5-(2-cyclohexyl-2-hydroxyethyl)-3-methylimidazolidin-4-one
  参考文献：
  名称：

  2-tert-Butyl-3-methyl-2,3-dihydroimidazol- 4-one-N-oxide:  A New Nitrone-Based Chiral Glycine Equivalent

  摘要：

  Cycloaddition reactions between a new homochiral imidazolone-derived nitrone afford cycloadclucts in high yield and with high stereoselectivity. Subsequent cycloadduct elaboration affords the gamma-lactones of gamma-hydroxy-alpha-amino acids as well as the optically pure amino acids themselves.

  DOI：

  10.1021/ol049505a
• 作为产物：
  描述：

  (2R)-2-(tert-butyl)-3-methylimidazolidin-4-one 在 urea-hydrogen peroxide 、 甲基三氧化铼(VII) 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到(R)-2-tert-butyl-3-methyl-2,3-dihydroimidazol-4-one N-oxide
  参考文献：
  名称：

  2-tert-Butyl-3-methyl-2,3-dihydroimidazol- 4-one-N-oxide:  A New Nitrone-Based Chiral Glycine Equivalent

  摘要：

  Cycloaddition reactions between a new homochiral imidazolone-derived nitrone afford cycloadclucts in high yield and with high stereoselectivity. Subsequent cycloadduct elaboration affords the gamma-lactones of gamma-hydroxy-alpha-amino acids as well as the optically pure amino acids themselves.

  DOI：

  10.1021/ol049505a

文献信息

• Tandem Addition/Cyclization of Alkynylzinc Reagents to Enantiopure 2-tert-Butyl-3,5-dimethyl-2,3-dihydroimidazol-4-oneN-Oxide: Potential Precursors of Quaternary α-Amino Acids
  作者：Frédéric Cantagrel、Sandra Pinet、Yves Gimbert、Pierre Y. Chavant

  DOI：10.1002/ejoc.200400861

  日期：2005.7

  A new enantiopure cyclic nitrone, a potential electrophilic alanine synthon, has been prepared. Its reaction with alkynylzinc reagents led to a tandem addition/cyclization reaction with complete regio- and stereoselectivity. The adducts are potential precursors of quaternary α-amino acids. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  一种新的对映体纯环硝酮，一种潜在的亲电子丙氨酸合成子，已被制备出来。它与炔基锌试剂的反应导致具有完全区域和立体选择性的串联加成/环化反应。加合物是季α-氨基酸的潜在前体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• 2-<i>tert</i>-Butyl-3-methyl-2,3-dihydroimidazol- 4-one-<i>N</i>-oxide:  A New Nitrone-Based Chiral Glycine Equivalent
  作者：Steven W. Baldwin、Alan Long

  DOI：10.1021/ol049505a

  日期：2004.5.1

  Cycloaddition reactions between a new homochiral imidazolone-derived nitrone afford cycloadclucts in high yield and with high stereoselectivity. Subsequent cycloadduct elaboration affords the gamma-lactones of gamma-hydroxy-alpha-amino acids as well as the optically pure amino acids themselves.