2-(1-chloro-1-lithioethyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole | 711020-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(1-chloro-1-lithioethyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole
• CAS: 711020-07-4
• 化学式: C₇H₁₁ClLiNO
• 分子量: 167.564
• InChiKey: DHJNVRVSXIPATQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(1-chloro-1-lithioethyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 、 环己烷 为溶剂， 反应 1.0h， 生成 (2R*,3S*)-2,3-epoxy-2-(4,4-dimethyl-2-oxazolin-2-yl)-3-p-tolylbutane
  参考文献：
  名称：

  Stereospecific β-Lithiation of Oxazolinyloxiranes:  Synthesis of α,β-Epoxy-γ-butyrolactones

  摘要：

  Stereospecific beta-lithlation of beta-aryl-substituted oxazollnyloxiranes is described. The trapping reaction of such reactive intermediates with carbonyl compounds gave alpha,beta-epoxy-gamma-butyrolactones after deblocking of the oxazoline moiety. This methodology has been also extended to the synthesis of optically active alpha,beta-epoxy-gamma-butyrolactones.

  DOI：

  10.1021/ol025781i
• 作为产物：
  描述：

  2-(1-chloroethyl)-4,4-dimethyl-2-oxazoline 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 2-(1-chloro-1-lithioethyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  On the Addition of Lithiated 2-Alkyl- and 2-(Chloroalkyl)-4,5-dihydro-1,3-oxazoles to Nitrones − A Mechanistic Investigation

  摘要：

  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.

  DOI：

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