(+/-)-1-<(methylbenzyl)amino>cyclopropanecarbonitrile | 137360-49-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-1-<(methylbenzyl)amino>cyclopropanecarbonitrile
• 英文别名: 1-(1-phenylethylamino)cyclopropane-1-carbonitrile
• CAS: 137360-49-7
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: PWLJGTQIHBUHOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.82
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1-<(methylbenzyl)amino>cyclopropanecarbonitrile 在 盐酸 作用下， 反应 12.0h， 以100%的产率得到1-(methylbenzyl)aminocylopropanecarboxylic acid hydrochloride
  参考文献：
  名称：

  从环丙烷酮缩醛中合成一种新的方便的1-氨基环丙烷甲酸酯基丙烯酸。

  摘要：

  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）。

  DOI：

  10.1016/s0040-4020(01)86558-3
• 作为产物：
  描述：

  1-乙氧基-1-三甲硅氧基环丙烷 、 氰化钾 、 α-苯乙胺 生成 (+/-)-1-<(methylbenzyl)amino>cyclopropanecarbonitrile
  参考文献：
  名称：

  Serotoninergic properties of new conformationally restricted benzamides

  摘要：

  A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C-3, C-4, C-5 and C-6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D-2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K-i = 9.03 nM; 5-HT4 K-i > 5000; D-2 K-i > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.

  DOI：

  10.1016/0223-5234(96)89139-2

文献信息

• Serotoninergic properties of new conformationally restricted benzamides
  作者：D Yang、B Brémont、S Shen、S Kefi、M Langlois

  DOI：10.1016/0223-5234(96)89139-2

  日期：1996.1

  A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C-3, C-4, C-5 and C-6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D-2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K-i = 9.03 nM; 5-HT4 K-i > 5000; D-2 K-i > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.
• 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）。