4,4-dimethyl-2-(2,6-dimethylphenyl)oxazoline | 133341-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-dimethyl-2-(2,6-dimethylphenyl)oxazoline
• 英文别名: 2-(2,6-dimethylphenyl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 133341-94-3
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: WIOQRPCWKLDLIR-UHFFFAOYSA-N

物化性质

• 沸点：
  302.9±31.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4,4-二甲基-2-苯基-2-噁唑啉 在 palladium diacetate 作用下， 反应 48.0h， 生成 4,4-dimethyl-2-(2,6-dimethylphenyl)oxazoline
  参考文献：
  名称：

  钯介导的2-芳基恶唑啉的正烷基化

  摘要：

  描述了2-芳基恶唑啉通过其环钯配合物与1-碘代烷烃的区域选择性邻烷基化。根据实验条件，可以选择性地制备2-或2,6-取代的衍生物。

  DOI：

  10.1016/0022-328x(91)86285-x

文献信息

• Optional ortho and lateral lithiations of 4,4-dimethyl-2-(o-tolyl)oxazolines
  作者：Naruki Tahara、Tsutomu Fukuda、Masatomo Iwao

  DOI：10.1016/s0040-4039(02)02318-3

  日期：2002.12

  4,4-Dimethyl-2-(o-tolyl)oxazolines 1 undergo normal lateral lithiation at the benzylic position by treatment with sec-BuLi in diethyl ether at −78°C. In contrast, metalation of 1 with sec-BuLi/TMEDA in diethyl ether at the same temperature leads to ortho-lithiation at the 6′-position. Rationalization for the unusual ortho-lithiation of 1 is proposed.

  通过在-78℃下在乙醚中用仲-BuLi处理4,4-二甲基-2-（邻甲苯基）恶唑啉1，在苄基位置进行正常的侧向锂化反应。相反，在相同温度下在乙醚中用仲-BuLi / TMEDA对1进行金属化会导致在6'-位发生邻位锂化。提出了对1的异常正交锂化的合理化方法。
• Palladium-Catalyzed Alkylation of Aryl C−H Bonds with sp³ Organotin Reagents Using Benzoquinone as a Crucial Promoter
  作者：Xiao Chen、Jiao-Jie Li、Xue-Shi Hao、Charles E. Goodhue、Jin-Quan Yu

  DOI：10.1021/ja0570943

  日期：2006.1.1

  The combination of directed C-H activation, batch-wise addition of tetraalkyltin reagents, and rate enhancement by benzoquinone and microwave irradiation provides a promising strategy for the direct coupling of C-H bonds with organometallic reagents. A variety of tetraalkyltins were coupled to C-H bonds to give the alkylated products in good yields by using 5 mol % Pd(OAc)2 as the catalyst. Benzoquinone was shown to be essential for the C-H activation when substrates containing non-pi-conjugated chelating groups are used. Monitoring the formation and reductive elimination of the Pd(Ar)(Me)L2 complex also revealed that benzoquinone promotes the reductive elimination step. Microwave irradiation enhances the reaction rate drastically. The versatility of this protocol was demonstrated by using substrates containing either oxazoline or pyridine as directing groups.