9-<1-(Benzotriazol-1-yl)-3-(dimethylamino)propyl>carbazole | 146041-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-<1-(Benzotriazol-1-yl)-3-(dimethylamino)propyl>carbazole
• 英文别名: N,N-dimethyl-3-(carbazol-9-yl)-3-(benzotriazol-1-yl)propanamine；3-(benzotriazol-1-yl)-3-carbazol-9-yl-N,N-dimethylpropan-1-amine
• CAS: 146041-80-7
• 化学式: C₂₃H₂₃N₅
• 分子量: 369.469
• InChiKey: HWYXTRVUDNIAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-<1-(Benzotriazol-1-yl)-3-(dimethylamino)propyl>carbazole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以59%的产率得到9-(3-(N,N-二甲基氨基)丙基)咔唑
  参考文献：
  名称：

  Additions of 1-(.alpha.-Aminoalkyl)benzotriazoles to N-Vinylamines and N-Vinylamides. A Novel and Versatile Method for the Preparation of Unsymmetrically Substituted 1,3-Diamines

  摘要：

  Additions of N,N-dialkyl-1H-benzotriazole-1-methanamines 1 to 9-vinylcarbazole followed by reduction of the adducts with lithium aluminum hydride gave the corresponding 9-(3-(dialkylamino)propyl)carbazoles 8 in good yield. Treatment of the adducts with Grignard reagents gave products 9 with an alkyl or aryl group at the C-1 atom of the propylene linkage. Use of alpha-phenyl-N,N-dialkyl-1H-benzotriazole-1-methanamine (14) in the addition led to the C-3 phenyl substituted products 15-18. Similar additions to N-vinyl-N-methylacetamide or 1-vinyl-2-pyrrolidinone followed by reduction of the adducts gave unsymmetrically substituted 1,3-propanediamines. Triamine 36 was obtained by condensation of ethylamine with formaldehyde and benzotriazole, addition of the product to 1-vinylpyrrolidinone, and reduction of the adduct with lithium aluminum hydride. 1,3-Propanediamine used in this process gave hexahydropyrimidine 39 while 1,6-hexanediamine gave hexamine 42.

  DOI：

  10.1021/jo00097a023
• 作为产物：
  描述：

  N,N-二甲基苯并三唑甲胺 、 N-乙烯基咔唑 以65%的产率得到
  参考文献：
  名称：

  Katritzky Alan R., Rachwal Stanislaw, Rachwal Bogumila, J. Org. Chem, 59 (1994) N 18, S 5206-5214

  摘要：

  DOI：

文献信息

• Method for producing optically active amines
  申请人：Nagasaki Izuru

  公开号：US20060100239A1

  公开（公告）日：2006-05-11

  The present invention provides a method for producing optically active amines of formula (9) or (10): which comprises reacting an imine equivalent of formula (6): with an alkene of formula (7) or an alkyne of formula (8): in the presence of a chiral catalyst, which method does not require additional procedures such as introduction and removal of protecting groups and gives said amines with high purity and high operability. The optically active amines are useful as synthetic 15 intermediates for pharmaceuticals, agrochemicals, etc.

  本发明提供一种制备光学活性胺的方法，其化学式为（9）或（10）：包括在手性催化剂的存在下，将化学式为（6）的亚胺当量与化学式为（7）的烯烃或化学式为（8）的炔烃反应，此方法不需要额外的保护基引入和去除等过程，并且可高纯度和高操作性地得到所述胺。这些光学活性胺可用作制药、农药等的合成中间体。
• Additions of 1-(aminomethyl)benzotriazoles to enamines, enamides, and vinyl ethers: novel routes to 1,3-diamines and tetrahydroquinolines
  作者：Alan R. Katritzky、Bogumila Rachwal、Stanislaw Rachwal

  DOI：10.1021/jo00056a006

  日期：1993.2

  New methods for the synthesis of 1,3-diamines and of 4-substituted tetrahydroquinolines are described in which the key step is the addition of the condensation products derived from amines, aldehydes, and benzotriazole to enamines, enamides, and vinyl ethers.
• Katritzky Alan R., Rachwal Stanislaw, Rachwal Bogumila, J. Org. Chem, 59 (1994) N 18, S 5206-5214
  作者：Katritzky Alan R., Rachwal Stanislaw, Rachwal Bogumila

  DOI：——

  日期：——
• Additions of 1-(.alpha.-Aminoalkyl)benzotriazoles to N-Vinylamines and N-Vinylamides. A Novel and Versatile Method for the Preparation of Unsymmetrically Substituted 1,3-Diamines
  作者：Alan R. Katritzky、Stanislaw Rachwal、Bogumila Rachwal

  DOI：10.1021/jo00097a023

  日期：1994.9

  Additions of N,N-dialkyl-1H-benzotriazole-1-methanamines 1 to 9-vinylcarbazole followed by reduction of the adducts with lithium aluminum hydride gave the corresponding 9-(3-(dialkylamino)propyl)carbazoles 8 in good yield. Treatment of the adducts with Grignard reagents gave products 9 with an alkyl or aryl group at the C-1 atom of the propylene linkage. Use of alpha-phenyl-N,N-dialkyl-1H-benzotriazole-1-methanamine (14) in the addition led to the C-3 phenyl substituted products 15-18. Similar additions to N-vinyl-N-methylacetamide or 1-vinyl-2-pyrrolidinone followed by reduction of the adducts gave unsymmetrically substituted 1,3-propanediamines. Triamine 36 was obtained by condensation of ethylamine with formaldehyde and benzotriazole, addition of the product to 1-vinylpyrrolidinone, and reduction of the adduct with lithium aluminum hydride. 1,3-Propanediamine used in this process gave hexahydropyrimidine 39 while 1,6-hexanediamine gave hexamine 42.