tert-butyl 1-benzyl-3-methyl-6-oxoperhydropyridazine-3-carboxylate | 528868-63-5

• 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: tert-butyl 1-benzyl-3-methyl-6-oxoperhydropyridazine-3-carboxylate
• 英文别名: Tert-butyl 1-benzyl-3-methyl-6-oxodiazinane-3-carboxylate
• CAS: 528868-63-5
• 化学式: C₁₇H₂₄N₂O₃
• 分子量: 304.389
• InChiKey: GMIGVDBUNXZHDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-benzyl-3-methyl-6-oxoperhydropyridazine-3-carboxylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到tert-butyl 1-benzylideneamino-2-methyl-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of α-Methylpyroglutamates from α,β-Didehydro α-Amino Acids

  摘要：

  A new method for the diastereoselective synthesis of alpha-methylpyroglutamates from alpha,beta-didehydro-N-(diphenylmethylene)glutamates has been developed. Deprotection of the (diphenylmethylene) amino moiety of the starting materials affords pyridazinone derivatives which can be transformed into alpha-methyl-6-oxoperhydropyridazine-3-carboxylates in a highly diastereoselective fashion. Ring contraction of the latter induced by LiHMDS affords alpha-methylpyroglutamates. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:24<4190::aid-ejoc4190>3.0.co;2-q
• 作为产物：
  描述：

  甲基溴化镁 、 1-benzyl-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxylic acid tert-butyl ester 在 ytterbium(III) triflate 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到tert-butyl 1-benzyl-3-methyl-6-oxoperhydropyridazine-3-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of α-Methylpyroglutamates from α,β-Didehydro α-Amino Acids

  摘要：

  A new method for the diastereoselective synthesis of alpha-methylpyroglutamates from alpha,beta-didehydro-N-(diphenylmethylene)glutamates has been developed. Deprotection of the (diphenylmethylene) amino moiety of the starting materials affords pyridazinone derivatives which can be transformed into alpha-methyl-6-oxoperhydropyridazine-3-carboxylates in a highly diastereoselective fashion. Ring contraction of the latter induced by LiHMDS affords alpha-methylpyroglutamates. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).

  DOI：

  10.1002/1099-0690(200212)2002:24<4190::aid-ejoc4190>3.0.co;2-q

文献信息

• Diastereoselective Synthesis of α-Methylpyroglutamates from α,β-Didehydro α-Amino Acids
  作者：Carlos Alvarez-Ibarra、Aurelio G. Csákÿ、Cristina Gómez de la Oliva

  DOI：10.1002/1099-0690(200212)2002:24<4190::aid-ejoc4190>3.0.co;2-q

  日期：2002.12

  A new method for the diastereoselective synthesis of alpha-methylpyroglutamates from alpha,beta-didehydro-N-(diphenylmethylene)glutamates has been developed. Deprotection of the (diphenylmethylene) amino moiety of the starting materials affords pyridazinone derivatives which can be transformed into alpha-methyl-6-oxoperhydropyridazine-3-carboxylates in a highly diastereoselective fashion. Ring contraction of the latter induced by LiHMDS affords alpha-methylpyroglutamates. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002).