4-(1,3-苯并恶唑-2-基)-N,N-二甲基苯胺 | 840-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(1,3-苯并恶唑-2-基)-N,N-二甲基苯胺
• 英文名称: 2-(p-dimethylaminophenyl)benzoxazole
• 英文别名: 4-(benzo[d]oxazol-2-yl)-N,N-dimethylaniline；2-(4-Dimethylamino-phenyl)-benzoxazol；4-(benzoxazol-2-yl)-N,N-dimethylaniline；2-(4-dimethylamino-phenyl)benzoxazole；Benzenamine, 4-(2-benzoxazolyl)-N,N-dimethyl-；4-(1,3-benzoxazol-2-yl)-N,N-dimethylaniline
• CAS: 840-57-3
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: NLWWHMRHFRTAII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N,N',N'-四甲基对苯二胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 sodium t-butanolate 、 三环己基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 4-(1,3-苯并恶唑-2-基)-N,N-二甲基苯胺
  参考文献：
  名称：

  Palladium-Catalyzed C–H Arylation of (Benzo)oxazoles or (Benzo)thiazoles with Aryltrimethylammonium Triflates

  摘要：

  The C-H arylation of (benzo)oxazoles or (benzo)thiazoles with aryltrimethylammonium triflates was carried out via Pd-catalyzed C-H/C-N cleavage. Oxazoles, thiazoles, benzoxazole, and benzothiazole were arylated using activated and deactivated aryltrimethylamrnonium triflates to give 2-aryl(benzo)oxazoles or 2-aryl(benzo)thiazoles in reasonable to excellent yields.

  DOI：

  10.1021/acs.orglett.5b02458

文献信息

• Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents
  作者：Bo Yang、Zhong-Xia Wang

  DOI：10.1021/acs.orglett.7b03145

  日期：2017.11.17

  Cross-coupling of (hetero)arylthiols with arylzinc reagents via C–S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.

  （杂）芳基硫醇与芳基锌试剂通过C–S裂解的交叉偶联是在无过渡金属的条件下进行的。该反应显示出广泛的底物范围和高官能团耐受性。富电子和不足的（杂）芳基硫醇和芳基锌试剂可用于该转化中。已证明Mg 2+和Li +离子可促进反应。
• Carbonates: eco-friendly solvents for palladium-catalysed direct arylation of heteroaromatics
  作者：Jia Jia Dong、Julien Roger、Cécile Verrier、Thibaut Martin、Ronan Le Goff、Christophe Hoarau、Henri Doucet

  DOI：10.1039/c0gc00229a

  日期：——

  The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature.

  这 钯环保型芳烃卤化物催化的各种杂芳族化合物与芳基卤化物的直接2-，4-或5-芳基化反应均能以中等至良好的收率进行 溶剂碳酸盐。使用以下方法可获得最佳产量苯并恶唑 或者 噻唑衍生品。这芳基化 的 呋喃， 噻吩， 吡咯， 咪唑 或者 异恶唑 发现衍生物需要更高的反应温度。
• Ni-Catalyzed C−F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles
  作者：Youzhi Yin、Xiaoyu Yue、Qi Zhong、Hanmin Jiang、Ruopeng Bai、Yu Lan、Hua Zhang

  DOI：10.1002/adsc.201701506

  日期：2018.4.17

  A Ni‐catalyzed C−F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system. A rapid synthesis of natural product texaline was also demonstrated using this protocol. This transformation could be potentially utilized in regioselective

  已开发了以恶唑为偶合伴侣的未活化芳基氟化物的Ni催化C-F键官能化。在Ni（cod）2 / IMes催化体系存在下，可以以中等至良好的产率获得各种芳基化的恶唑。使用该方案还证明了天然产物texaline的快速合成。该转化可潜在地用于后期合成应用中恶唑基的区域选择性引入。
• Pd/Cu bimetallic co-catalyzed direct 2-arylation of benzoxazole with aryl chloride
  作者：Ling-Li Zheng、Bo Yin、Xing-Chuan Tian、Ming-Yong Yuan、Xiao-Huan Li、Feng Gao

  DOI：10.1016/j.tetlet.2019.151316

  日期：2019.12

  An efficient Palladium/Copper bimetallic co-catalyzed direct 2-arylation of benzoxazoles with aryl chlorides is presented. The Pd(OAc)2/CuI/NiXantphos-based catalyst enables the installation of various aryl and heteroaryl groups in good to excellent yields (75–99%). Preliminary mechanism investigation indicates that Pd/Nixantphos complex activates C-Cl bond of aryl chlorides via oxidative addition

  提出了一种有效的钯/铜双金属共催化的苯并恶唑与芳基氯化物的2-芳基化反应。基于Pd（OAc）2 / CuI / NiXantphos的催化剂能够以优异的产率（75-99％）安装各种芳基和杂芳基。初步的机理研究表明，Pd / Nixantphos配合物通过氧化加成激活芳基氯的C-Cl键，而Cu / Nixantphos配合物与氮原子螯合以降低苯并恶唑中2-H的pK a。
• Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides
  作者：Feng Gao、Byeong-Seon Kim、Patrick J. Walsh

  DOI：10.1039/c4cc05307a

  日期：——

  The first room-temperature direct 2-arylation of benzoxazoles with aryl bromides by a Pd(OAc)₂/NiXantphos-based catalyst is reported.

  第一个室温下使用Pd(OAc)₂/NiXantphos基催化剂对苯并噁唑与芳基溴化物进行直接2-芳基化反应的研究结果已经报道。