1-phenyl-N-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)methanimine | 292055-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 1-phenyl-N-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)methanimine
• CAS: 292055-63-1
• 化学式: C₂₂H₁₇N
• 分子量: 295.384
• InChiKey: XNNHSMLKIXMLRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-N-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)methanimine 、 反丁烯二腈 以 xylene 为溶剂， 反应 48.0h， 生成 (3R,4R)-5-phenylspiro[pyrrolidine-2,2'-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene]-3,4-dicarbonitrile
  参考文献：
  名称：

  X = Y-ZH系统为潜在的1,3-偶极子。ZH质子在亚胺中的活化

  摘要：

  一系列取代基能够通过激活CH质子而在亚胺中诱导热1，3-偶极子形成，如用双亲性试剂进行的捕获实验所示。

  DOI：

  10.1016/s0040-4039(00)88342-2
• 作为产物：
  描述：

  5-氨基-5H-二苯并(a,d)环庚烯 、 苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到1-phenyl-N-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)methanimine
  参考文献：
  名称：

  Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides

  摘要：

  A new method to synthesize chiral alpha-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.

  DOI：

  10.1021/ol200456y

文献信息

• Mapping the Active Site in a Chemzyme: Diversity in the <i>N</i>-Substituent in the Catalytic Asymmetric Aziridination of Imines
  作者：Yu Zhang、Zhenjie Lu、Aman Desai、William D. Wulff

  DOI：10.1021/ol802431v

  日期：2008.12.4

  The active site of the aziridination catalyst derived from either the VANOL or VAPOL ligand and B(OPh)(3) is larger than expected and can accommodate not only significant substitution on the diarylmethyl unit of the imine but also that alkyl (but not perfluorylalkyl) substituents on the aryl groups lead to enhanced rates and enantioselection. The screen of diarylmethyl N-substituents on the imine revealed that the 3,5-di-tert-butyldianisylmethyl group (BUDAM) gave exceptionally high asymmetric inductions for imines of aryl aldehydes.
• Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched α-Amino Phosphine Oxides
  作者：Gajendrasingh K. Ingle、Yuxue Liang、Michael G. Mormino、Guilong Li、Frank R. Fronczek、Jon C. Antilla

  DOI：10.1021/ol200456y

  日期：2011.4.15

  A new method to synthesize chiral alpha-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity.
• X=Y-ZH systems as potential 1,3-dipoles. Activation of the ZH proton in imines
  作者：R. Grigg、H.Q.N. Gunaratne、V. Sridharan、S. Thianpatanagul、M. Tute

  DOI：10.1016/s0040-4039(00)88342-2

  日期：1983.1

  A range of substituents is capable of inducing thermal 1,3-dipole formation in imines by activation of the CH proton as shown by trapping experiments with dipolarophiles.

  一系列取代基能够通过激活CH质子而在亚胺中诱导热1，3-偶极子形成，如用双亲性试剂进行的捕获实验所示。