4,5-dihydro-1,3-oxazole-2-carbaldehyde

• 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: 4,5-dihydro-1,3-oxazole-2-carbaldehyde
• 英文别名: 2-formyl-4,4-dimethyl-2-oxazoline；4,4-dimethyl-5H-1,3-oxazole-2-carbaldehyde
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: VZWCVMYUWHZTEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-chloromethyl-4,4-dimethyl-4,5-dihydro-1,3-oxazole 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 3.0h， 生成 4,5-dihydro-1,3-oxazole-2-carbaldehyde
  参考文献：
  名称：

  A highly stereoselective synthesis of α,β-unsaturated oxazolines

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)02025-1

文献信息

• An alternative approach to differentially substituted 2-oxazoline chalcogen derivatives
  作者：Murilo B.M. de Mello、Giuliano C. Clososki、Leandro Piovan、Alfredo R.M. de Oliveira

  DOI：10.1016/j.jorganchem.2015.06.022

  日期：2015.10

  chalcogen atom as a tether element. Alkylation of 2-tosyloximethylene-2-oxazoline with an appropriate sodium, lithium or potassium alkoxide yielded the corresponding ether. Introduction of sulfur or selenium was easily accomplished using the corresponding sodium salts. The 77Se NMR for alkyl or aryl 2-methylene-2-oxazoline selenides shows good correlation with the electronegativity pattern of substituents

  在这项研究中，我们提出了一种替代方法，以获得几种含有硫属元素原子作为系链元素的取代的单或双-2-恶唑啉。用适当的钠，锂或钾的醇盐将2-甲苯并氧亚甲基-2-恶唑啉烷基化，得到相应的醚。使用相应的钠盐很容易完成硫或硒的引入。在77烷基或芳基2-亚甲基-2-恶唑啉硒化物的Se NMR与取代基的电负性模式显示出良好的相关性。大多数含有恶唑啉基硫属元素的产品在通常的实验条件下是稳定的。然而，碲衍生物对光和氧表现出不同寻常的敏感性，通过非常复杂的机械途径分解。作为该氧化过程的结果，首次可以分离出4,4-二甲基-2-恶唑啉-2-甲醛，并以17％的收率对其进行完全表征。
• 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.
• 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.