4,4-dimethyl-2-(1-phenylcyclohexyl)oxazoline | 874895-86-0

• 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-(1-phenylcyclohexyl)oxazoline
• 英文别名: 4,4-dimethyl-2-(1-phenylcyclohexyl)-5H-1,3-oxazole
• CAS: 874895-86-0
• 化学式: C₁₇H₂₃NO
• 分子量: 257.376
• InChiKey: HFGIWFMOAZEZJR-UHFFFAOYSA-N

物化性质

• 沸点：
  353.5±21.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-(1-phenylcyclohexyl)oxazoline 在 palladium diacetate 碘苯二乙酸 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以95%的产率得到4,5-dihydro-2-(1-(2-iodophenyl)cyclohexyl)-4,4-dimethyloxazole
  参考文献：
  名称：

  Remote C–H bond functionalization reveals the distance-dependent isotope effect

  摘要：

  Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.026
• 作为产物：
  描述：

  1-苯基-1-环己羧酸 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 4,4-dimethyl-2-(1-phenylcyclohexyl)oxazoline
  参考文献：
  名称：

  Palladium-Catalyzed Alkylation of Aryl C−H Bonds with sp³ Organotin Reagents Using Benzoquinone as a Crucial Promoter

  摘要：

  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.

  DOI：

  10.1021/ja0570943

文献信息

• 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.
• Remote C–H bond functionalization reveals the distance-dependent isotope effect
  作者：Jiao-Jie Li、Ramesh Giri、Jin-Quan Yu

  DOI：10.1016/j.tet.2008.03.026

  日期：2008.7

  Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage. (C) 2008 Elsevier Ltd. All rights reserved.