[(2R,3R)-1-benzyl-3-phenylazetidin-2-yl]-phenylmethanimine | 853732-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: [(2R,3R)-1-benzyl-3-phenylazetidin-2-yl]-phenylmethanimine
• CAS: 853732-36-2
• 化学式: C₂₃H₂₂N₂
• 分子量: 326.441
• InChiKey: BFBQBSYHBOHCJA-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(2R,3R)-1-benzyl-3-phenylazetidin-2-yl]-phenylmethanimine 在 sodium tetrahydroborate 、 silica gel 作用下， 以 乙醚 、 乙醇 、 Petroleum ether 为溶剂， 反应 1.5h， 生成 (1'S,2R,3R)-(1-benzyl-3-phenylazetidin-2-yl)phenylmethanol
  参考文献：
  名称：

  Synthesis of enantiopure 2-acyl azetidines and the application of amino alcohols derived therefrom in enantioselective catalysis

  摘要：

  Enantiopure 2-acyl azetidines were prepared in good yields from 2-cyano azetidines. The ketones produced were then stereo selectively reduced with sodium borohydride (with or without zinc bromide) or transformed into tertiary azetidinic amino alcohols by addition of phenyllithium. The latter compounds were found to be highly efficient catalysts for the enantioselective addition of diethylzinc to aldehydes, giving enantioselectivities up to 98%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00710-3
• 作为产物：
  描述：

  苯基锂 、 (2R,3R)-1-benzyl-3-phenyl-azetidine-2-carbonitrile 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 [(2R,3R)-1-benzyl-3-phenylazetidin-2-yl]-phenylmethanimine
  参考文献：
  名称：

  Azetidines as ligands in the Pd(II) complexes series

  摘要：

  The preparation of palladium (II) complexes having sterically congested azetidines as ligands is described. Diastereomerically pure alpha-alkylamino and alpha-alkylimino azetidines react with Na2PdCl4 to afford the corresponding bidendate Pd(II) complexes, whereas 2-cyano azetidines can be used to access bidendate Pd(11) complexes containing an amino-imidate moiety. Preliminary study of the catalytic activity of these new complexes in the Suzuki cross-coupling reaction is presented. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.02.041

文献信息

• Keller, Laurent; Sanchez, Monica Vargas; Prim, Damien, Journal of Organometallic Chemistry, <hi>2005</hi>, vol. 690, p. 2306 - 2311
  作者：Keller, Laurent、Sanchez, Monica Vargas、Prim, Damien、Couty, Francois、Evano, Gwilherm、Marrot, Jerome

  DOI：——

  日期：——
• Synthesis of enantiopure 2-acyl azetidines and the application of amino alcohols derived therefrom in enantioselective catalysis
  作者：François Couty、Damien Prim

  DOI：10.1016/s0957-4166(02)00710-3

  日期：2002.11

  Enantiopure 2-acyl azetidines were prepared in good yields from 2-cyano azetidines. The ketones produced were then stereo selectively reduced with sodium borohydride (with or without zinc bromide) or transformed into tertiary azetidinic amino alcohols by addition of phenyllithium. The latter compounds were found to be highly efficient catalysts for the enantioselective addition of diethylzinc to aldehydes, giving enantioselectivities up to 98%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Azetidines as ligands in the Pd(II) complexes series
  作者：Laurent Keller、Monica Vargas Sanchez、Damien Prim、François Couty、Gwilherm Evano、Jérome Marrot

  DOI：10.1016/j.jorganchem.2005.02.041

  日期：2005.4

  The preparation of palladium (II) complexes having sterically congested azetidines as ligands is described. Diastereomerically pure alpha-alkylamino and alpha-alkylimino azetidines react with Na2PdCl4 to afford the corresponding bidendate Pd(II) complexes, whereas 2-cyano azetidines can be used to access bidendate Pd(11) complexes containing an amino-imidate moiety. Preliminary study of the catalytic activity of these new complexes in the Suzuki cross-coupling reaction is presented. (c) 2005 Elsevier B.V. All rights reserved.