1-aza[6]helicene N-oxide | 1115257-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-aza[6]helicene N-oxide
• 英文别名: 4-Oxido-4-azoniahexacyclo[12.12.0.02,11.03,8.017,26.020,25]hexacosa-1(14),2(11),3(8),4,6,9,12,15,17(26),18,20,22,24-tridecaene；4-oxido-4-azoniahexacyclo[12.12.0.02,11.03,8.017,26.020,25]hexacosa-1(14),2(11),3(8),4,6,9,12,15,17(26),18,20,22,24-tridecaene
• CAS: 1115257-04-9；1115257-02-7；1114905-10-0
• 化学式: C₂₅H₁₅NO
• 分子量: 345.4
• InChiKey: CCEZBILJNQALKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 1-aza[6]helicene N-oxide 在 4-甲苯磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(-)-(M)-2-tert-butylamino-1-aza[6]helicene
  参考文献：
  名称：

  Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts

  摘要：

  Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The heticene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).

  DOI：

  10.1021/ja100539c
• 作为产物：
  描述：

  (M)-1-aza[6]helicene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以32%的产率得到1-aza[6]helicene N-oxide
  参考文献：
  名称：

  螺旋手性吡啶N-氧化物：不对称催化剂的新家族。

  摘要：

  DOI：

  10.1002/anie.200803338

文献信息

• Helical Chiral Pyridine<i>N</i>-Oxides: A New Family of Asymmetric Catalysts
  作者：Norito Takenaka、Robindro Singh Sarangthem、Burjor Captain

  DOI：10.1002/anie.200803338

  日期：2008.12.1
• Helical Chiral 2-Aminopyridinium Ions: A New Class of Hydrogen Bond Donor Catalysts
  作者：Norito Takenaka、Jinshui Chen、Burjor Captain、Robindro Singh Sarangthem、Appayee Chandrakumar

  DOI：10.1021/ja100539c

  日期：2010.4.7

  Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The heticene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).
• Helical Chiral 2,2′-Bipyridine <i>N-</i> Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane
  作者：Jinshui Chen、Burjor Captain、Norito Takenaka

  DOI：10.1021/ol200102c

  日期：2011.4.1

  A highly enantioselective synthesis of homopropargylic alcohols is achieved by using the new helical chiral 2,2'-bipyridine N-monoxide catalyst and allenyltrichlorosilane. This method can be further extended to the enantio- and regioselective propargylation of N-acylhydrazones.