2-hexyl-2-methyloxazolidine | 60871-03-6

• 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-hexyl-2-methyloxazolidine
• 英文别名: 2-Hexyl-2-methyl-1,3-oxazolidine
• CAS: 60871-03-6
• 化学式: C₁₀H₂₁NO
• 分子量: 171.283
• InChiKey: ITJDXGFSYUTVQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-hexyl-2-methyloxazolidine 以 甲苯 为溶剂， 反应 18.0h， 生成 1-(2-Hexyl-2-methyl-oxazolidin-3-yl)-ethanone
  参考文献：
  名称：

  Synthesis and Mosquito Repellent Properties of 2,2-Dialkyl- and 2-Alkyl-4,4-dimethyl-N-acetyloxazolidines

  摘要：

  Nineteen novel N-acetyl-2,2-dialkyloxazolidines (2) and N-acetyl-2-alkyl-4,4-dimethyloxazolidines (3) were synthesized from commercially available carbonyl compounds and ethanolamine or 2-amino-2-methyl-1-propanol. Their bioactivity against laboratory-reared mosquitoes was compared in patch tests to known N-acetyl-2-alkyloxazolidines (1) and N,N-diethyl-m-toluamide (deet insect repellent). Isomeric composition measurements by [C-13]NMR spectroscopy favoured the Z rotational isomer for samples of 2 (91-96% Z) and the E rotational isomer for samples of 3 (66-71% E), in agreement with molecular mechanics calculations on rotational isomers of model oxazolidines. Samples of 1 were previously shown to exist in solution mostly as the Z isomer (60-70% Z). Within the optimal molecular weight range for these experimental chemicals, the duration of repellency against Aedes aegypti (L.), Anopheles quadrimaculatus Say and Anopheles albimanus Wiedemann generally followed the order: 1 > 2 > deet > 3. Bioassay data are discussed in relation to the equilibrium populations of rotational isomers for substituted N-acetyloxazolidines.

  DOI：

  10.1002/(sici)1096-9063(199604)46:4<307::aid-ps368>3.0.co;2-v
• 作为产物：
  描述：

  1-辛炔 、 C.I.酸性橙108 在 三苯基膦双(三氟甲磺酰亚胺)金 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到2-hexyl-2-methyloxazolidine
  参考文献：
  名称：

  具有独特区域选择性的可重复使用的金（I）催化剂，用于炔烃的分子间加氢胺化

  摘要：

  带有低配位双（三氟甲磺酰基）亚氨酸酯配体的两个金（I）膦配合物，即AuSPhosNTf 2和AuPPh 3 NTf 2是在温和的反应条件下内部和末端炔烃区域选择性分子间加氢胺化的活性催化剂。所述催化剂显示基于电子而非空间因素的区域选择性，这允许优先合成与先前描述的区域异构体相反的区域异构体。这种微妙的化学和区域选择性取决于所用的催化剂，底物和反应条件，并允许人们进行新的串联反应。这些金（I）配合物在自由溶剂条件下运行，不排除空气，不添加酸性助催化剂，可以通过在己烷中的简单沉淀进行定量回收和再利用。

  DOI：

  10.1002/adsc.200900491

文献信息

• US3943143A
  申请人：——

  公开号：US3943143A

  公开（公告）日：1976-03-09
• US3976648A
  申请人：——

  公开号：US3976648A

  公开（公告）日：1976-08-24
• US3987017A
  申请人：——

  公开号：US3987017A

  公开（公告）日：1976-10-19
• US4008244A
  申请人：——

  公开号：US4008244A

  公开（公告）日：1977-02-15
• Synthesis and Mosquito Repellent Properties of 2,2-Dialkyl- and 2-Alkyl-4,4-dimethyl-<i>N</i>-acetyloxazolidines
  作者：Wesley G. Taylor、Tse W. Hall、Carl E. Schreck

  DOI：10.1002/(sici)1096-9063(199604)46:4<307::aid-ps368>3.0.co;2-v

  日期：1996.4

  Nineteen novel N-acetyl-2,2-dialkyloxazolidines (2) and N-acetyl-2-alkyl-4,4-dimethyloxazolidines (3) were synthesized from commercially available carbonyl compounds and ethanolamine or 2-amino-2-methyl-1-propanol. Their bioactivity against laboratory-reared mosquitoes was compared in patch tests to known N-acetyl-2-alkyloxazolidines (1) and N,N-diethyl-m-toluamide (deet insect repellent). Isomeric composition measurements by [C-13]NMR spectroscopy favoured the Z rotational isomer for samples of 2 (91-96% Z) and the E rotational isomer for samples of 3 (66-71% E), in agreement with molecular mechanics calculations on rotational isomers of model oxazolidines. Samples of 1 were previously shown to exist in solution mostly as the Z isomer (60-70% Z). Within the optimal molecular weight range for these experimental chemicals, the duration of repellency against Aedes aegypti (L.), Anopheles quadrimaculatus Say and Anopheles albimanus Wiedemann generally followed the order: 1 > 2 > deet > 3. Bioassay data are discussed in relation to the equilibrium populations of rotational isomers for substituted N-acetyloxazolidines.