(E)-4,4-dimethyl-2-[2-(2,4,6-trimethoxyphenyl)vinyl]-4,5-dihydro-1,3-oxazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4,4-dimethyl-2-[2-(2,4,6-trimethoxyphenyl)vinyl]-4,5-dihydro-1,3-oxazole
• 英文别名: 4,4,6-Trimethoxy-phenyl)-vinyl]-4,5-dihyd ro-oxazole；4,4-dimethyl-2-[(E)-2-(2,4,6-trimethoxyphenyl)ethenyl]-5H-1,3-oxazole
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: VVNYWIFDVGUMQM-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4,4-三甲基-2-恶唑 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 生成 (E)-4,4-dimethyl-2-[2-(2,4,6-trimethoxyphenyl)vinyl]-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

文献信息

• A highly stereoselective synthesis of α,β-unsaturated oxazolines
  作者：Vito Capriati、Leonardo Degennaro、Saverio Florio、Renzo Luisi

  DOI：10.1016/s0040-4039(01)02025-1

  日期：2001.12

  Lithiated 2,4,4-trimethyl-2-oxazoline 2a and 2-chloromethyl-4.4-dimethyl-2-oxazoline 2b react smoothly with a number of nitrones 3 to produce alpha,beta -unsaturated oxazolines 6 and 7 highly stereoselectively. (C) 2001 Elsevier Science Ltd. All rights reserved.