5-chloro-N,N-diethylbenzo[d]oxazol-2-amine | 1262297-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-chloro-N,N-diethylbenzo[d]oxazol-2-amine
• 英文别名: 5-chloro-N,N-diethyl-1,3-benzoxazol-2-amine
• CAS: 1262297-10-8
• 化学式: C₁₁H₁₃ClN₂O
• 分子量: 224.69
• InChiKey: MHEPQIQFYFBOGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 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：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-2-氨基苯酚 在 氧气 、 copper(II) acetate monohydrate 、 苯甲酸 作用下， 反应 12.0h， 生成 5-chloro-N,N-diethylbenzo[d]oxazol-2-amine
  参考文献：
  名称：

  在温和条件下，铜催化苯并恶唑与甲酰胺或仲胺的直接CH-H胺化反应

  摘要：

  已经开发了一种简便，有效且实用的方法，用于铜催化的苯甲恶唑与甲酰胺或仲胺的CH–H氨化反应。该系统可以在没有外部碱的情况下进行，仅需要O 2或什至空气作为氧化剂。合成了各种取代的苯并恶唑-2-胺，产率中等至优异。

  DOI：

  10.1021/jo200447x

文献信息

• Copper-Catalyzed Oxidative Amination of Benzoxazoles via C−H and C−N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources
  作者：Shengmei Guo、Bo Qian、Yinjun Xie、Chungu Xia、Hanmin Huang

  DOI：10.1021/ol1030298

  日期：2011.2.4

  method for oxidative amination of azoles with tertiary amines via copper-catalyzed C−H and C−N bond activation has been developed. This protocol can be performed in the absence of external base and only requires atmospheric oxygen as oxidant. The catalyst system is very simple and efficient, which opens a new way for using tertiary amines as nitrogen group sources for C−N bond formation reactions.

  通过铜催化的CH和CN键活化作用，开发了一种高效，概念上新颖的用叔胺氧化唑类胺的方法。该方案可以在不存在外部碱的情况下进行，并且仅需要大气中的氧气作为氧化剂。催化剂体系非常简单和高效，这为使用叔胺作为C-N键形成反应的氮源提供了新途径。
• Metal-Free Synthesis of 2-<i>N</i>,<i>N</i>-Dialkylaminobenzoxazoles Using Tertiary Amines as the Nitrogen Source
  作者：Mookda Pattarawarapan、Dolnapa Yamano、Nitaya Wiriya、Wong Phakhodee

  DOI：10.1021/acs.joc.9b00797

  日期：2019.5.17

  The unprecedented reaction of tertiary amines with 2(3H)-benzoxazolones has been investigated. In the presence of the Ph3P–I2 reagent system, the reaction of both acyclic and cyclic aliphatic tertiary amines led to the formation of 2-N,N-dialkylaminobenzoxazoles with the selective cleavage of an alkyl group. Especially, N-(2-iodoethyl)piperazinyl derivatives were rapidly produced in good yields when

  已研究了叔胺与2（3 H）-苯并恶唑酮的空前反应。在Ph 3 P–I 2试剂体系的存在下，无环和环状脂族叔胺的反应均导致2- N，N-二烷基氨基苯并恶唑的形成，并选择性地裂解了烷基。特别地，当使用DABCO作为氮源时，N-（2-碘乙基）哌嗪基衍生物以高收率快速生产。仅在底物的亲核性超过胺的亲核性的情况下，苯并恶唑酮的竞争性自缩合才优先进行。31 P 11 H-NMR研究表明涉及芳氧基phosph中间体和/或可能的2-碘苯并恶唑，其激活苯并恶唑酮的C-2位朝亲核芳族取代。
• ^<i>n</i>Bu₄NI-catalyzed direct amination of benzoxazoles with tertiary amines using TBHP as oxidant under microwave irradiation
  作者：Jin-Wei Yuan、Ming Jin、Qiu-Yue Yin、Pu Mao、Ling-Bo Qu

  DOI：10.1515/znb-2015-0212

  日期：2016.4.1

  Abstract A facile, efficient, and practical method for nBu4NI-catalyzed direct C–H amination of benzoxazoles with tertiary amines has been developed. The system could be performed in the absence of metal catalyst and only requires tert-butyl hydroperoxide as oxidant under microwave irradiation. A variety of substituted benzoxazol-2-amines were synthesized with moderate to good yield.

  摘要 已经开发了一种简便、高效且实用的方法，用于 nBu4NI 催化的苯并恶唑与叔胺的直接 C-H 胺化。该系统可以在没有金属催化剂的情况下进行，并且在微波辐射下只需要叔丁基过氧化氢作为氧化剂。合成了多种取代的苯并恶唑-2-胺，收率中等至良好。
• Cobalt- and Manganese-Catalyzed Direct Amination of Azoles under Mild Reaction Conditions and the Mechanistic Details
  作者：Ji Young Kim、Seung Hwan Cho、Jomy Joseph、Sukbok Chang

  DOI：10.1002/anie.201005922

  日期：2010.12.17

  azoles has been developed using peroxide and an acid additive to couple various types of azoles with ammonia, and primary or secondary amines (see scheme). The catalyst loadings are low, the optimal reaction conditions are mild, and the substrate scope is broad. The product azoles are an important pharmacophore of high biological activity.

  关键时刻：使用过氧化物和酸添加剂将各种类型的唑与氨，伯胺或仲胺偶联，开发了一种新的钴或锰催化的唑胺胺化方法（请参见方案）。催化剂负载量低，最佳反应条件温和，底物范围广。产物唑类是具有高生物活性的重要药效团。
• Identification, synthesis and strategy for minimization of potential impurities in the synthesis of suvorexant
  作者：Xunlei Lv、Jing Pan、Weiyuan Liu、Xue Meng、Liang Chen、Ting Zhou、Kuaile Lin、Deyong Ye、Weicheng Zhou

  DOI：10.1080/00397911.2021.1930055

  日期：2021.7.18

  Abstract Eight process-related impurities in the synthesis of suvorexant were identified, while six of them were described for the first time. In order to get the references for the process optimization and quality control of API, the eight compounds were synthesized. According to the possible formation pathways, a modified synthesis and the strategy for impurity control in the corresponding reactions

  摘要 在 suvorexant 的合成过程中鉴定出 8 种与工艺相关的杂质，其中 6 种是首次描述。为了给原料药的工艺优化和质量控制提供参考，合成了8种化合物。根据可能的形成途径，建立了相应反应中的改进合成和杂质控制策略。