4,4-dimethyl-2-[2-(prop-2-enyl)]phenyl-2-oxazoline | 133341-93-2

• 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-(prop-2-enyl)]phenyl-2-oxazoline
• 英文别名: 4,5-dihydro-4,4-dimethyl-2-[2-(2-propen-1-yl)phenyl]oxazole；4,4-dimethyl-2-(2-prop-2-enylphenyl)-5H-1,3-oxazole
• CAS: 133341-93-2
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: MEHUSAMXTIYGOB-UHFFFAOYSA-N

物化性质

• 沸点：
  318.3±21.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-[2-(prop-2-enyl)]phenyl-2-oxazoline 在 9-硼双环[3.3.1]壬烷 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.5h， 以87.7%的产率得到3-(2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl)propan-1-ol
  参考文献：
  名称：

  Assessment of dopamine D1 receptor affinity and efficacy of three tetracyclic conformationally-restricted analogs of SKF38393

  摘要：

  To assess the effect of conformational mobility on receptor activity, the beta-phenyl substituent of dopamine D-1 agonist ligands of the phenylbenzazepine class, (+/-)-6,6a, 7,8,9,13b-hexahydro-5H-benzo[d] naphtho[ 2,1-b] azepine-11,12-diol (8), and its oxygen and sulfur bioisosteres 9 and 10, respectively, were synthesized as conformationally-restricted analogs of SKF38393, a dopamine D-1-selective partial agonist. Compounds trans-8b, 9, and 10 showed binding affinity comparable to that of SKF38393, but functionally, they displayed only very weak agonist activity. These results suggest that the conformationally-restricted structure of the analogs cannot adopt a binding orientation that is necessary for agonist activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.057
• 作为产物：
  描述：

  4,4-二甲基-2-苯基-2-噁唑啉 、 3-溴丙烯 在 正丁基锂 、 copper(I) bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以58%的产率得到4,4-dimethyl-2-[2-(prop-2-enyl)]phenyl-2-oxazoline
  参考文献：
  名称：

  Cyclization of Aryl Acyl Radicals Generated from S-(4-Cyano)phenyl Thiolesters by a Nickel Complex Catalyzed Electroreduction

  摘要：

  Aromatic acyl radicals generated from S-(4-cyano)phenyl 2-alkenylthiobenzoate by a nickel complex catalyzed electroreduction undergo 5- and 6-exo cyclization to give 1-indanone and dihydro-1-naphthalenone derivatives, respectively.

  DOI：

  10.1021/jo0268512

文献信息

• Directed regioselective <i>ortho</i>,<i>ortho</i>′-magnesiations of aromatics and heterocycles using <i>s</i>Bu₂Mg in toluene
  作者：Andreas Hess、Jan P. Prohaska、Sabrina B. Doerrich、Florian Trauner、Ferdinand H. Lutter、Sébastien Lemaire、Simon Wagschal、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1039/d1sc01777b

  日期：——

  functionalized either by Pd-catalyzed arylation or by trapping reactions with a broad range of electrophiles (aldehydes, ketones, allylic halides, acyl chlorides, Weinreb amides, aryl halides, hydroxylamine benzoates, terminal alkynes). Furthermore, several double ortho,ortho′-magnesiations were realized in the case of aryl oxazolines, N-aryl pyrazoles as well as 2-aryl-2H-1,2,3-triazoles by simply repeating the

  芳基唑类作为生物活性化合物是普遍存在的，其区域选择性功能化具有极其重要的合成意义。在这里，我们报告了可溶于甲苯的二烷基镁基s Bu 2 Mg的开发。这种新试剂可以对各种N-芳基化吡唑和 1,2,3-三唑以及带有恶唑啉、磷酸二酰胺或酰胺导向基团的芳烃进行温和的区域选择性邻位镁化。所得二芳基镁试剂通过 Pd 催化的芳基化或通过与多种亲电子试剂（醛、酮、烯丙基卤、酰氯、Weinreb 酰胺、芳基卤、苯甲酸羟胺、末端炔）的捕获反应进一步官能化。此外，在芳基恶唑啉、N-芳基吡唑以及2-芳基-2H -1,2,3-三唑的情况下，通过简单地重复镁化/亲电试剂捕获序列，实现了几种双邻位、邻'-镁化，从而允许有价值的1,2,3-功能化芳烃的制备。
• Palladium-mediated ortho-alkylation of 2-aryloxazolines
  作者：J.C. Clinet、G. Balavoine

  DOI：10.1016/0022-328x(91)86285-x

  日期：1991.3

  The regioselective ortho-alkylation of 2-aryloxazolines through the reaction of their cyclopalladated complexes with 1-iodoalkanes is described. Depending upon the experimental conditions, either 2- or 2,6-substituted derivatives can be selectively prepared.

  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。
• Reactions of cyclopalladated complexes with boronic acids
  作者：Purna Chandra Rao Vasireddy、Irina P. Smoliakova

  DOI：10.1016/j.ica.2022.121114

  日期：2022.11

  were obtained from N,N-dimethylhydrazone of d-camphor, and had different absolute configurations of the chiral center attached to the metal. Both reactions yielded the same isomer, (1R,3R,4R,Z)-1,1-dimethyl-2-[1,7,7-trimethyl-(4-nitrophenyl)bicyclo[2.2.1]heptan-2-ylidene]hydrazine, as the major product. The X-ray crystallographic study of this product proved the R absolute configuration of the new chiral

  六种已知的C ( sp 2 ) ,N和C ( sp 3 ) ,N环钯化络合物衍生自N,N-二甲基苄胺、4,4-二甲基-2-苯基-2-恶唑啉、2-叔丁基-2,2合成了-二甲基-2-恶唑啉、d-樟脑的O-甲基肟、8-甲基喹啉和d-樟脑的N,N-二甲基腙，并用于与芳基、苄基和烯丙基硼酸或酯的C-C键形成反应。成功的 C 的两个协议开发了C联轴器；两者都涉及使用碱和将二聚环钯化络合物转化为具有PPh 3作为辅助配体的单核衍生物。C( sp 2 )–C( sp 2 ) 键的形成是通过N,N-二甲基苄胺和 4,4-二甲基-2-苯基-2-恶唑啉的单核配合物与 ArB(OH) 2在丙酮中在 60 °C 在 Cs 2 CO 3存在下。(i) C ( sp 3 ) ,N配合物 PPh 3 - 6 , PPh 3 - 8和 PPh的反应3 - 10与 ArB(OH) 2 (Ar = Ph, p -NO 2 C 6
• Leukotriene antagonists
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0296731B1

  公开（公告）日：1992-08-26
• EP0532674A4
  申请人：——

  公开号：EP0532674A4

  公开（公告）日：1993-04-07