2-tert-butyl-4,4,8,8-tetramethyl-3-phenyl-1,6-dioxa-2,9-diazaspiro[4.4]nonane | 497846-65-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2-tert-butyl-4,4,8,8-tetramethyl-3-phenyl-1,6-dioxa-2,9-diazaspiro[4.4]nonane
• CAS: 497846-65-8
• 化学式: C₁₉H₃₀N₂O₂
• 分子量: 318.459
• InChiKey: XSPCYVRJRBLBFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  33.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-tert-butyl-4,4,8,8-tetramethyl-3-phenyl-1,6-dioxa-2,9-diazaspiro[4.4]nonane 在 palladium on activated charcoal 水 、 氢气 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 生成 3-tert-butylamino-2,2-dimethyl-3-phenylpropanoic acid
  参考文献：
  名称：

  New Synthesis of Optically Active 5-Isoxazolidinones and β-Amino Acids

  摘要：

  A new simple and stereoselective synthesis of 5-isoxazolidinones based on the reaction of lithiated 2-isopropyl-2-oxazolines with nitrones is described. A chiral version of such a methodology allows the preparation of highly enantioenriched 5-isoxazolidinones which are useful precursors for the synthesis of beta-amino acids.

  DOI：

  10.1021/jo035356i
• 作为产物：
  描述：

  2-异丙基-4,4-二甲基-4,5-二氢-1,3-噁唑 、 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 1.0h， 以70%的产率得到2-tert-butyl-4,4,8,8-tetramethyl-3-phenyl-1,6-dioxa-2,9-diazaspiro[4.4]nonane
  参考文献：
  名称：

  New Synthesis of Optically Active 5-Isoxazolidinones and β-Amino Acids

  摘要：

  A new simple and stereoselective synthesis of 5-isoxazolidinones based on the reaction of lithiated 2-isopropyl-2-oxazolines with nitrones is described. A chiral version of such a methodology allows the preparation of highly enantioenriched 5-isoxazolidinones which are useful precursors for the synthesis of beta-amino acids.

  DOI：

  10.1021/jo035356i

文献信息

• On the Addition of Lithiated 2-Alkyl- and 2-(Chloroalkyl)-4,5-dihydro-1,3-oxazoles to Nitrones − A Mechanistic Investigation
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi

  DOI：10.1002/1099-0690(200209)2002:17<2961::aid-ejoc2961>3.0.co;2-f

  日期：2002.9

  The addition of 2-(lithioalkyl)-4,5-dihydro-1,3-oxazoles 2a-c and 2-[chloro(lithio)alkyl]-4,5-dihydro-1,3-oxazoles 2d,e to nitrones 3 has been studied. While lithiated 2-methyl-4,5-dihydro-1,3-oxazole 2a adds stereoselectively to nitrones 3, resulting after long reaction times (3 h) in the formation of 2-[(E)-alkenyl]-4,5-dihydro-1,3-oxazoles 8a-h, lithiated 2(chloromethyl)-4,5-dihydro-1,3-oxazole 2e affords 2-[(Z)-alkenyl]-4,5-dihydro-1,3-oxazoles 26a-d and 26f-h. alpha-Lithiated 2-ethyl-4,5-dihydro-1,3-oxazole 2b adds to 3a to give the 1,6-dioxa-2,9-diazaspiro[4.4]nonane 9 and 2-alkenyl-4,5-dihydro-1,3-oxazole 14 after treatment with oxalic acid. Quenching after short reaction times shows that the conversions of 2a to 8 and of 2b to 14 go through spirocyclic compounds 7 and 9, while the reaction between 2e and 3a, quenched even at short reaction times, gives a mixture of the 1,6-dioxa-2,9diazaspiro[4.4]nonanes 21-H and 22-H and the 2-(1,2-oxazetidin-4-yl)-4,5-dihydro-1,3-oxazoles 25a and 27a. The addition of 2c to 3a furnishes the 1,6-dioxa-2,9-diazaspiro[4.4]nonane 15 and then isoxazolidin-5-one 16 upon hydrolysis with oxalic acid. The addition of 2d to 3a gives the 1,6-dioxa-2,9-diazaspiro[4.4]nonanes 17b and 18b after short reaction times and the 2-(1,2-oxazetidin-4-yl)-4,5-dihydro-1,3-oxazole 19 after long reaction times. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
• New Synthesis of Optically Active 5-Isoxazolidinones and β-Amino Acids
  作者：Renzo Luisi、Vito Capriati、Saverio Florio、Teresa Vista

  DOI：10.1021/jo035356i

  日期：2003.12.1

  A new simple and stereoselective synthesis of 5-isoxazolidinones based on the reaction of lithiated 2-isopropyl-2-oxazolines with nitrones is described. A chiral version of such a methodology allows the preparation of highly enantioenriched 5-isoxazolidinones which are useful precursors for the synthesis of beta-amino acids.