1-<(dibenzyl)amino>cyclopropanecarbonitrile | 137360-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<(dibenzyl)amino>cyclopropanecarbonitrile
• 英文别名: 1-(dibenzylamino)cyclopropanecarbonitrile；1-(Dibenzylamino)cyclopropane-1-carbonitrile
• CAS: 137360-51-1
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: PSYFFJYKQMSNCN-UHFFFAOYSA-N

物化性质

• 沸点：
  408.2±33.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<(dibenzyl)amino>cyclopropanecarbonitrile 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 生成 methyl N-[[1-(dibenzylamino)cyclopropyl]-phenylmethyl]carbamate
  参考文献：
  名称：

  Synthesis, modelling and NK1 antagonist evaluation of a non-rigid cyclopropane-containing analogue of CP-99,994

  摘要：

  A non-rigid cyclopropane-containing diamine analogue of CP-99,994 was synthesised and was found to have only moderate NK1 receptor binding affinity. Molecular dynamics calculations of the conformational space of the former compound gave good correlation between observed activity and a recently published pharmacophore model, lending predictive value to the latter. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00020-8
• 作为产物：
  描述：

  N,N-dibenzylaminoacetonitrile 在 六甲基磷酰三胺 、 三氧化硫 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-<(dibenzyl)amino>cyclopropanecarbonitrile
  参考文献：
  名称：

  Guillaume, Dominique; Brum-Bousquet, Michele; Aitken, David J, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 4, p. 391 - 396

  摘要：

  DOI：

文献信息

• A new and convenient synthesis of 1-aminocyclopropanecar☐ylic acid from cyclopropanone acetal.
  作者：Antoine Fadel

  DOI：10.1016/s0040-4020(01)86558-3

  日期：1991.8

  Cyclopropanone acetal 2a undergoes the one-pot Strecker synthesis under sonication to provide the amino nitrile 8, which after hydrolysis and catalytic hydrogenolysis, gives 1-aminocyclopropanecar☐ylic acid (ACC, 1) in good overall yield.

  环丙烷酮缩醛2a在超声处理下进行一锅式Strecker合成，提供氨基腈8，该氨基腈在水解和催化氢解后，以良好的总收率得到1-氨基环丙烷甲酸酯基丙烯酸（ACC，1）。
• An original synthesis of trans-1,2-diaminocyclobutane
  作者：Fabrice Vergne、Karolin Partogyan、David J. Aitken、Henri-Philippe Husson

  DOI：10.1016/0040-4020(95)01091-2

  日期：1996.2

  A new synthesis of trans-1,2-diaminocyclobutane 1 is described, in which the key feature is the novel stereoselective borane-induced reductive ring-expansion reaction of the cyclopropane-iminonitrile 2 to give the cyclobutane 4. This latter intermediate was also used to prepare a trans-fused rigid analogue of moclobemide.

  描述了反式-1,2-二氨基环丁烷1的新合成，其中的主要特征是新颖的立体选择性硼烷诱导的环丙烷-亚胺2的还原性环扩环反应，得到环丁烷4。后者的中间体也用于制备吗氯贝胺的转熔刚性类似物。
• Guillaume, Dominique; Brum-Bousquet, Michele; Aitken, David J, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 4, p. 391 - 396
  作者：Guillaume, Dominique、Brum-Bousquet, Michele、Aitken, David J、Husson, Henri-Philippe

  DOI：——

  日期：——
• Synthesis, modelling and NK1 antagonist evaluation of a non-rigid cyclopropane-containing analogue of CP-99,994
  作者：David J. Aitken、Sandrine Ongeri、Danielle Vallée-Goyet、Jean-Claude Gramain、Henri-Philippe Husson

  DOI：10.1016/s0960-894x(01)00020-8

  日期：2001.3

  A non-rigid cyclopropane-containing diamine analogue of CP-99,994 was synthesised and was found to have only moderate NK1 receptor binding affinity. Molecular dynamics calculations of the conformational space of the former compound gave good correlation between observed activity and a recently published pharmacophore model, lending predictive value to the latter. (C) 2001 Elsevier Science Ltd. All rights reserved.