2-(2-cyclohexyl-1-methyl-ethyl)-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine | 41625-76-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 2-(2-cyclohexyl-1-methyl-ethyl)-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine
• 英文别名: 2-(1-cyclohexyl-2-propyl)-4,4,6-trimethyl-5,6-dihydro-1,3-4H-oxazine；2-(2-Cyclohexyl-1-methylethyl)-4,4,6-trimethyl-5,6-dihydro-4H-1,3-oxazine；2-(1-cyclohexylpropan-2-yl)-4,4,6-trimethyl-5,6-dihydro-1,3-oxazine
• CAS: 41625-76-7
• 化学式: C₁₆H₂₉NO
• 分子量: 251.412
• InChiKey: OWVAIECJLPGTET-UHFFFAOYSA-N

物化性质

• 沸点：
  321.5±11.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基-2,4-戊二醇 生成 2-(2-cyclohexyl-1-methyl-ethyl)-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine
  参考文献：
  名称：

  Syntheses via dihydro-1,3-oxazines. VII. A simple synthesis of unsymmetrical ketones

  摘要：

  DOI：

  10.1021/ja01049a041

文献信息

• Synthesis of aldehydes and products of such synthesis
  申请人：Board of Supervisors of Louisiana State University and Agricultural &

  公开号：US04131623A1

  公开（公告）日：1978-12-26

  The disclosure describes the production of complex aliphatic, unsaturated and cycloalkane aldehydes utilizing heterocyclic ring compounds, such as oxazines, particularly dihydro-1,3-oxazines. The oxazines are treated with an alkali metal-alkane compound, such as butyl lithium in the presence of an organic solvent at subzero temperature to form an anion of the oxazine. This anion is then alkylated in the anhydrous reaction mixture by introduction of a suitable halide, epoxide or ketone while still at a subzero temperature and mixture is permitted to warm up to room temperature, following which the reaction mixture is acidified, as with hydrochloric acid to pH 2 to 3, extracted and then made basic, as with caustic alkali with cooling. The reaction mixture is then extracted, as with ether, to produce after evaporation the alkylated dihydro-1,3-oxazine. The alkylated dihydro-1,3-oxazine is then reacted with an alkali metal or sodium borohydride or borodeuteride or borotritide, with cooling to subzero temperatures at about a neutral pH and then transferred into a basic aqueous environment following extraction of the aqueous layer with an organic solvent, such as ether, to give a tetrahydro-1,3-oxazine. This compound may then be converted to the aldehyde desired by steam distillation or by hydrolysis in the presence of a dilute or weak acid, such as hydrochloric or oxalic acid. The aldehydes may then be extracted. These aldehydes are useful as components or intermediates in flavoring or perfumes, in insect attractants and repellants, and in pharmaceuticals.

  该披露描述了利用杂环环化合物（如噁嗪，特别是二氢-1,3-噁嗪）生产复杂的脂肪族、不饱和和环烷烃醛。将噁嗪与碱金属-烷基化合物（如丁基锂）在有机溶剂存在下在零下温度下处理，形成噁嗪的负离子。然后在仍处于零下温度的无水反应混合物中通过引入适当的卤化物、环氧化物或酮基进行烷基化，然后允许混合物升温至室温，随后将反应混合物酸化，如用盐酸调至pH值为2至3，提取后再使其碱性化，如用碱性碱液并陪冷却。然后通过提取（如用醚）处理反应混合物，蒸发后得到烷基化的二氢-1,3-噁嗪。然后将烷基化的二氢-1,3-噁嗪与碱金属或硼氢化钠或硼氘化钠或硼三氚化钠反应，在中性pH值下在零下温度下进行冷却，然后在提取水层与有机溶剂（如醚）后转移到碱性水环境中，得到四氢-1,3-噁嗪。然后可以通过蒸馏或在稀释或弱酸（如盐酸或草酸）存在下水解将该化合物转化为所需的醛。然后可以提取这些醛。这些醛可用作香料或香水的成分或中间体，在昆虫引诱剂和驱避剂以及制药中有用。
• US4131623A
  申请人：——

  公开号：US4131623A

  公开（公告）日：1978-12-26
• Syntheses via dihydro-1,3-oxazines. VII. A simple synthesis of unsymmetrical ketones
  作者：Albert Irving Meyers、Albert C. Kovelesky

  DOI：10.1021/ja01049a041

  日期：1969.10