N-(benzoxazol-2-yl)-N,N',N'-trimethyl-ethane-1,2-diamine

• 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: N-(benzoxazol-2-yl)-N,N',N'-trimethyl-ethane-1,2-diamine
• 英文别名: N¹-(benzo[d]oxazol-2-yl)-N1,N2,N2-trimethylethane-1,2-diamine；N'-(1,3-benzoxazol-2-yl)-N,N,N'-trimethylethane-1,2-diamine
• 化学式: C₁₂H₁₇N₃O
• 分子量: 219.286
• InChiKey: QJAOCLAFKPUZGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯苯并恶唑 、 N,N,N'-三甲基乙二胺 在 bis(acetylacetonate)nickel(II) polymethylhydrosiloxane 、 sodium t-butanolate 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 18.0h， 以84%的产率得到N-(benzoxazol-2-yl)-N,N',N'-trimethyl-ethane-1,2-diamine
  参考文献：
  名称：

  An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides

  摘要：

  A new silane-promoted nickel-catalyzed amination of aryl chlorides with 0.5 mol % of Ni(acac)2, 1 mol% of 3,5,6,8-tetrabromo-1, 10-phenanthroline, and polymethythydrosiloxane was developed. A broad range of aryl and heteroaryl chlorides can be coupled with secondary amines and anilines to give the desired (het)arylamines in good to excellent yields. The reaction is sensitive to the nature and amount of the silane promoter.

  DOI：

  10.1021/jo702219f

文献信息

• 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。
• An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides
  作者：Georg Manolikakes、Andrei Gavryushin、Paul Knochel

  DOI：10.1021/jo702219f

  日期：2008.2.1

  A new silane-promoted nickel-catalyzed amination of aryl chlorides with 0.5 mol % of Ni(acac)2, 1 mol% of 3,5,6,8-tetrabromo-1, 10-phenanthroline, and polymethythydrosiloxane was developed. A broad range of aryl and heteroaryl chlorides can be coupled with secondary amines and anilines to give the desired (het)arylamines in good to excellent yields. The reaction is sensitive to the nature and amount of the silane promoter.