2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzonitrile | 118559-28-7

• 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-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzonitrile
• 英文别名: 2-(4',4'-dimethyl-2'-oxazolinyl)benzonitrile；2-(4,4-dimethyl-5H-1,3-oxazol-2-yl)benzonitrile
• CAS: 118559-28-7
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: YITGJNWCVLEQQT-UHFFFAOYSA-N

物化性质

• 熔点：
  46-48 °C
• 沸点：
  140 °C(Press: 2 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzonitrile 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以79%的产率得到2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-3-iodobenzonitrile
  参考文献：
  名称：

  Selective functionalization of cyano-phenyl-2-oxazolines using TMPMgCl·LiCl

  摘要：

  Metalated phenyl-2-oxazolines bearing cyano groups can be selectively obtained through the reaction of TMPMgCl center dot LiCl with the appropriate substrate. Subsequent reaction with different electrophiles furnished the functionalized derivatives in good yields. Density functional theory (DFT) calculations were performed to evaluate the influence of the ring substituents on the acidity of the aromatic hydrogens. Application to the synthesis of novel functionalized phthalides illustrates the great potential of the methodology to the synthesis of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.09.051
• 作为产物：
  描述：

  4,4-二甲基-2-氧唑啉 、 2-溴苯腈 生成 2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzonitrile
  参考文献：
  名称：

  Palladium-Catalyzed Coupling of Oxazol-2-yl- and 2-Oxazolin-2-yltrimethylstannanes with Aromatic Halides. A New Entry to 2-Aryl and 2-Heteroaryl Oxazoles and Oxazolines

  摘要：

  4-甲基恶唑和4,4-二甲基-2-恶唑啉用正丁基锂和三甲基氯化锡反应得到相应的2-三甲基甲锡烷基衍生物，在四(三苯基膦)钯(0)催化剂存在下发生交叉偶联与各种芳基和杂芳基卤化物反应，以高产率得到2-芳基和2-杂芳基恶唑和恶唑啉。

  DOI：

  10.1055/s-1987-28047

文献信息

• Nitrile-substituted 2-(oxazolinyl)-phenols: minimalistic excited-state intramolecular proton transfer (ESIPT)-based fluorophores
  作者：Dominik Göbel、Daniel Duvinage、Tim Stauch、Boris J. Nachtsheim

  DOI：10.1039/d0tc00776e

  日期：——

  intramolecular proton transfer (ESIPT)-based fluorophores as powerful solid-state emitters. The very simple synthesis gave access to all four regioisomers of nitrile-substituted 2-(oxazolinyl)-phenols (MW = 216.1). In respect of their emission properties they can be divided into aggregation-induced emission enhancement (AIEE) luminophores (1-CN and 2-CN), dual state emission (DSE) emitters (3-CN) and aggregation-caused

  在本文中，我们提出了简约的单苯，激发态分子内质子转移（ESIPT）基荧光团作为强大的固态发射器。非常简单的合成，得到访问腈取代的2-（恶唑啉基）-phenols的所有四个区域异构体（中号w ^ = 216.1）。就其发射特性而言，它们可分为聚集诱发发射增强（AIEE）发光体（1-CN和2-CN），双态发射（DSE）发射体（3-CN）和聚集引起的猝灭（ACQ）荧光团（4-CN）。值得注意的是，使用化合物1-CN，我们发现了一种基于ESIPT的简约荧光团，在固态Φ中具有极高的量子产率˚F =在87.3％ λ EM = 491纳米。此外，在溶液中量子产率的测定高达Φ ˚F = 63.0％，结合斯托克斯向上移动直到11.310厘米-1。与温度有关的发射图，晶体结构分析和与时间有关的密度泛函理论（TDDFT）计算对发射特性的起源提供了深刻的了解。
• An efficient synthesis of cyanoarenes and cyanoheteroarenes via lithiation followed by electrophilic cyanation
  作者：Nobuhiro Sato、Qi Yue

  DOI：10.1016/s0040-4020(03)00985-2

  日期：2003.7

  arenes and heteroarenes into the ortho-cyano derivatives was achieved through directed lithiation followed by electrophilic cyanation with phenyl cyanate. This reaction method proved to be applicable to halogen–lithium exchanged intermediates, so especially useful for the synthesis of benzonitriles. The scope of the reaction sequence was explored using a number of substrates.

  一锅法将单取代的芳烃和杂芳烃转化为邻氰基衍生物是通过定向锂化，然后用氰酸苯酯进行亲电氰化来实现的。事实证明，该反应方法适用于卤素-锂交换的中间体，因此特别适用于合成苄腈。使用多种底物探索了反应序列的范围。
• Aerobic C(sp²)–H Hydroxylations of 2-Aryloxazolines: Fast Access to Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores
  作者：Dominik Göbel、Nils Clamor、Enno Lork、Boris J. Nachtsheim

  DOI：10.1021/acs.orglett.9b01350

  日期：2019.7.19

  The direct hydroxylation of 2-aryloxazolines via a deprotonative magnesiation using TMPMgCl center dot LiCl and subsequent oxidation with molecular oxygen or air as a green oxidant is reported. This method proceeds under mild conditions at room temperature with high regioselectivity and chemoselectivity. The obtained phenols exhibit tunable luminescence properties, induced by excited-state intramolecular proton transfer. This method opens a new opportunity for the sustainable synthesis of luminescent organic molecules.
• DONDONI, A.;FANTIN, G.;FOGAGNOLO, M.;MEDICI, A.;PEDRINI, P., SYNTHESIS,(1987) N 8, 693-696
  作者：DONDONI, A.、FANTIN, G.、FOGAGNOLO, M.、MEDICI, A.、PEDRINI, P.

  DOI：——

  日期：——
• Selective functionalization of cyano-phenyl-2-oxazolines using TMPMgCl·LiCl
  作者：Leandro A. Bozzini、João H.C. Batista、Murilo B.M. de Mello、Ricardo Vessecchi、Giuliano C. Clososki

  DOI：10.1016/j.tetlet.2017.09.051

  日期：2017.11

  Metalated phenyl-2-oxazolines bearing cyano groups can be selectively obtained through the reaction of TMPMgCl center dot LiCl with the appropriate substrate. Subsequent reaction with different electrophiles furnished the functionalized derivatives in good yields. Density functional theory (DFT) calculations were performed to evaluate the influence of the ring substituents on the acidity of the aromatic hydrogens. Application to the synthesis of novel functionalized phthalides illustrates the great potential of the methodology to the synthesis of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved.