2-tert-butyl-4'-cyano-diphenyl ether

• 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: 2-tert-butyl-4'-cyano-diphenyl ether
• 英文别名: 4-(2-Tert-butylphenoxy)benzonitrile
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: WJNFDMMDOLFZFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二聚氰胺 、 2-tert-butyl-4'-cyano-diphenyl ether 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以60%的产率得到6-(4-(2-(tert-butyl)phenoxy)phenyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  De, Suparna S.; Vogalu, Siva K.; Ansari, Nazima, Journal of the Indian Chemical Society, 2020, vol. 97, # 8, p. 1211 - 1215

  摘要：

  DOI：
• 作为产物：
  描述：

  2-叔丁基苯酚 、 对氟苯腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以77%的产率得到2-tert-butyl-4'-cyano-diphenyl ether
  参考文献：
  名称：

  Synthesis of Diaryl Ethers, Diaryl Sulfides, Heteroaryl Ethers and Heteroaryl Sulfides under Microwave Dielectric Heating

  摘要：

  本文描述了利用微波加热技术合成二芳基醚和硫化物的方法。该方法在芳基卤与缺电子酚或苯硫酚的SNAr反应中表现出快速、高效的特点。该方法的应用范围可扩展到含有羟基的六元杂环化合物，以及2-嘧啶硫醇与适度活化的芳基卤的反应，分别得到杂芳基醚和硫化物。目前方法的优势包括广泛的底物适用性、无需金属催化剂、产品分离简便以及高纯度。

  DOI：

  10.1055/s-2005-865321

文献信息

• Synthesis of Diaryl Ethers, Diaryl Sulfides, Heteroaryl Ethers and Heteroaryl Sulfides under Microwave Dielectric Heating
  作者：Quanrui Wang、Feng Li、Qingqing Meng、Huansheng Chen、Zhiming Li、Fenggang Tao

  DOI：10.1055/s-2005-865321

  日期：——

  This paper describes the synthesis of diaryl ethers and sulfides by utilizing microwave heating methodology. The methodology is shown to be rapid and efficient for the coupling of phenols or thiophenol with electron-deficient aryl halides through a SNAr reaction. The scope of the protocol can be expanded to six-membered heterocycles bearing a hydroxyl group as well as to the reaction of 2-pyrimidinethiol with mildly activated aryl halides, providing heteroaryl ethers and sulfides, respectively. The advantages of the present method include the wide substrate scope, the obviation of metal catalysts, ease of product isolation, and high purity of products.

  本文描述了利用微波加热技术合成二芳基醚和硫化物的方法。该方法在芳基卤与缺电子酚或苯硫酚的SNAr反应中表现出快速、高效的特点。该方法的应用范围可扩展到含有羟基的六元杂环化合物，以及2-嘧啶硫醇与适度活化的芳基卤的反应，分别得到杂芳基醚和硫化物。目前方法的优势包括广泛的底物适用性、无需金属催化剂、产品分离简便以及高纯度。
• Diaryl ether synthesis in supercritical carbon dioxide in batch and continuous flow modes
  作者：Jin-Kyun Lee、Matthew J. Fuchter、Rachel M. Williamson、Gary A. Leeke、Edward J. Bush、Ian F. McConvey、Simon Saubern、John H. Ryan、Andrew B. Holmes

  DOI：10.1039/b808374f

  日期：——

  A high yielding, batch mode synthesis of diaryl ethers and sulfides by an SNAr fluoride-mediated process in scCO2 has been developed; the use of a polymer-supported imidazolium fluoride reagent in batch mode led to the development of a fixed-bed continuous flow process, with high conversions.

  已开发出一种在超临界二氧化碳中通过SNAr氟化物介导过程高效合成二芳基醚和硫醚的批量模式合成方法；在批量模式下使用聚合物支撑的咪唑氟化物试剂，促成了固定床连续流动过程的发展，并实现了高转化率。
• P(i-BuNCH2CH2)3N: an efficient promoter for the microwave synthesis of diaryl ethers
  作者：Steven M. Raders、John G. Verkade

  DOI：10.1016/j.tetlet.2008.03.089

  日期：2008.5

  of aryl fluorides with aryl TBDMS ethers under microwave conditions gave moderate to high yields of the desired products at low catalyst loadings and in short times. In this methodology, electron deficient aryl fluorides possessing substituents, such as nitro, cyano, and ester, were coupled with sterically demanding aryl TBDMS ethers as well as with aryl TBDMS ethers bearing a variety of functionalities

  用标题的原氮杂磷杂环戊烷作为促进剂，在微波条件下芳基氟化物与芳基TBDMS醚的偶联在低催化剂负载量和短时间内得到中等至高产率的所需产物。在这种方法中，将具有取代基（例如硝基，氰基和酯）的缺电子的芳基氟化物与空间需求的芳基TBDMS醚以及带有各种官能团（例如甲氧基，卤素和氰基）的芳基TBDMS醚偶联。
• P(<i>i</i>-BuNCH₂CH₂)₃N:  An Efficient Promoter for the Nucleophilic Aromatic Substitution Reaction of Aryl Fluorides with Aryl TBDMS (or TMS) Ethers
  作者：Sameer Urgaonkar、John G. Verkade

  DOI：10.1021/ol051108s

  日期：2005.7.1

  [reaction: see text]. The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and aryl TBDMS (or TMS) ethers has been shown to be efficiently promoted by proazaphosphatranes such as P(i-BuNCH(2)CH(2))(3)N (3). Excellent yields of diaryl ether products were obtained under unusually mild conditions.

  [反应：请参见文字]。缺电子的芳基氟化物和芳基TBDMS（或TMS）醚之间的亲核芳族取代反应已显示出可以通过原七磷烷（例如P（i-BuNCH（2）CH（2））（3）N（3）有效地促进。在异常温和的条件下，可获得优异的二芳基醚产品收率。
• Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride−Alumina and 18-Crown-6:  Expansion of Scope and Utility¹
  作者：J. Scott Sawyer、Elisabeth A. Schmittling、Jayne A. Palkowitz、William J. Smith

  DOI：10.1021/jo980800g

  日期：1998.9.1

  An efficient alternative to the Ullmann ether synthesis of diaryl ethers, diaryl thioethers, and diarylamines involving the SNAr addition of a phenol, thiophenol, or aniline to an appropriate aryl halide, mediated by potassium-fluoride alumina and 18-crown-6 in acetonitrile or DMSO, is described. Expansion of the reaction conditions to include DMSO as solvent has resulted in a far greater range of substitution patterns permitted on the electrophile. For example, it was found that electronically unfavorable S-chlorobenzonitrile could be condensed with 3-methoxyphenol to form the corresponding diaryl ether in 66% yield, a combination not normally amenable to Ullmann coupling. Electron-withdrawing groups present on the electrophile may be as diverse as nitro, cyano, formyl, acetyl, ester, amide, and even aryl. The method features a simple reaction procedure that provides products in generally good to excellent purified yields.