(+/-)-N-<(tert-butylimino)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine | 124070-07-1

• 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: (+/-)-N-<(tert-butylimino)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine
• 英文别名: (+/-)-N-[(tert-butylimino)methyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine；1-(16-azatetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaen-16-yl)-N-tert-butylmethanimine
• CAS: 124070-07-1
• 化学式: C₂₀H₂₂N₂
• 分子量: 290.408
• InChiKey: DHKPRVRHDMBYMD-UHFFFAOYSA-N

物化性质

• 熔点：
  63-64 °C
• 沸点：
  409.3±55.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-N-<(tert-butylimino)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 硫酸 、 氰化钠 、 氨 、 仲丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 52.5h， 生成 (+/-)-5-(aminomethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine
  参考文献：
  名称：

  Synthesis and structure-activity relationship of C5-substituted analogs of (.+-.)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5, 10-imine [(.+-.)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site

  摘要：

  A series of eight C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (1) have been prepared by the directed lithiation-alkylation (and acylation) of its (+-)-N-tert-butylformamidinyl derivative 2 followed by formamidine solvolysis. An additional 10 analogues were prepared by elaboration of the C5-ethyl ester derivative. Analogues possessing large (e.g. propyl and larger) lipophilic substituents displace [3H]-1-(1-thienylcyclohexyl)piperidine [( 3H]TCP) from the high-affinity phencyclidine (PCP) binding site in rat brain homogenates only at high concentrations (Ki greater than 1000 nM); however, the presence of a polar amino functionality (e.g. 2-aminoethyl) offsets this effect (Ki = 20 nM). Thus, the boundary condition for lipophilic substituents larger than ethyl appears to be polar in nature. Interaction of the 11 relatively small (MR less than 14) C5-substituted analogues of 1 with the high-affinity PCP binding site associated with the N-methyl-D-aspartate (NMDA) receptor is best described by the equation log (1/Ki) = -5.83F + 0.64 pi + 7.41 (r = 0.90).

  DOI：

  10.1021/jm00165a029
• 作为产物：
  描述：

  10,11-dihydro-5H-dibenzocyclohepten-5,10-imine 、 N′-叔丁基-N,N-二甲基甲脒 在 ammonium sulfate 作用下， 以 甲苯 为溶剂， 反应 144.0h， 以96%的产率得到(+/-)-N-<(tert-butylimino)methyl>-10,11-dihydro-5H-dibenzocyclohepten-5,10-imine
  参考文献：
  名称：

  Synthesis and structure-activity relationship of C5-substituted analogs of (.+-.)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5, 10-imine [(.+-.)-desmethyl-MK801]: ligands for the NMDA receptor-coupled phencyclidine binding site

  摘要：

  A series of eight C5-substituted analogues of (+-)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine (1) have been prepared by the directed lithiation-alkylation (and acylation) of its (+-)-N-tert-butylformamidinyl derivative 2 followed by formamidine solvolysis. An additional 10 analogues were prepared by elaboration of the C5-ethyl ester derivative. Analogues possessing large (e.g. propyl and larger) lipophilic substituents displace [3H]-1-(1-thienylcyclohexyl)piperidine [( 3H]TCP) from the high-affinity phencyclidine (PCP) binding site in rat brain homogenates only at high concentrations (Ki greater than 1000 nM); however, the presence of a polar amino functionality (e.g. 2-aminoethyl) offsets this effect (Ki = 20 nM). Thus, the boundary condition for lipophilic substituents larger than ethyl appears to be polar in nature. Interaction of the 11 relatively small (MR less than 14) C5-substituted analogues of 1 with the high-affinity PCP binding site associated with the N-methyl-D-aspartate (NMDA) receptor is best described by the equation log (1/Ki) = -5.83F + 0.64 pi + 7.41 (r = 0.90).

  DOI：

  10.1021/jm00165a029

文献信息

• J. Med. Chem. 1990, 33, 1069-1076
  作者：

  DOI：——

  日期：——