(+/-)-trans-1-Aminomethyl-2-phenyl-cyclopropan

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (+/-)-trans-1-Aminomethyl-2-phenyl-cyclopropan
• 英文别名: ((1S,2S)-2-Phenylcyclopropyl)methanamine；[(1S,2S)-2-phenylcyclopropyl]methanamine
• 化学式: C₁₀H₁₃N
• 分子量: 147.22
• InChiKey: ATTLDOZXPZCOGK-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-1-Aminomethyl-2-phenyl-cyclopropan 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 1.25h， 生成 trans-1-(aminomethyl)-2-phenylcyclopropane hydrochloride
  参考文献：
  名称：

  Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

  摘要：

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

  DOI：

  10.1021/jm801354e
• 作为产物：
  描述：

  2-苯基环丙烷羧酸 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-trans-1-Aminomethyl-2-phenyl-cyclopropan
  参考文献：
  名称：

  Kaiser,C. et al., Journal of medicinal and pharmaceutical chemistry, 1962, vol. 5, p. 1243 - 1265

  摘要：

  DOI：

文献信息

• Towards nitrile-substituted cyclopropanes – a slow-release protocol for safe and scalable applications of diazo acetonitrile
  作者：Katharina J. Hock、Robin Spitzner、Rene M. Koenigs

  DOI：10.1039/c7gc00602k

  日期：——

  Diazo acetonitrile has long been neglected despite its high value in organic synthesis due to a high risk of explosions. Herein, we report our efforts towards the transient and safe generation of this diazo compound, its applications in iron catalyzed cyclopropanation and cyclopropenation reactions and the gram-scale synthesis of cyclopropyl nitriles.

  尽管重氮乙腈在有机合成中具有很高的价值，但由于爆炸的高风险，长期以来一直被人们忽略。在本文中，我们报告了我们对这种重氮化合物的瞬态和安全生成，其在铁催化的环丙烷化和环丙烷化反应中的应用以及克级合成环丙基腈的努力。
• A Short Stereoselective Synthesis of a Cyclopropyl Analog of γ-Aminobutyric acid (GABA)
  作者：Debendra K. Mohapatra

  DOI：10.1080/00397919908085899

  日期：1999.12.1

  Abstract An efficient synthesis of (S,S)-2-(aminomethyl) cyclopropane carboxylic acid has been achieved in 7 steps (38% overall yield) starting from commercially available cinnamyl alcohol. The synthesis involves initial stereoselective formation of the functionalized cyclopropane derivative 5 and its further transformation to the desired product.

  摘要 以市售肉桂醇为原料，(S,S)-2-(氨基甲基) 环丙烷羧酸的高效合成分 7 步完成（总产率为 38%）。该合成涉及官能化环丙烷衍生物 5 的初始立体选择性形成及其向所需产物的进一步转化。
• 5-HT2C Receptor Agonists as Anorectic Agents
  申请人：Kozikowski Alan

  公开号：US20090203750A1

  公开（公告）日：2009-08-13

  This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.

  本发明涉及调节5-HT2家族受体的化合物，特别是调节5-HT2C受体的化合物。本发明的化合物包括5-HT2C受体的激动剂和选择性激动剂。本发明的化合物包括5-HT2C受体的选择性激动剂，其在5-HT2A受体和/或5-HT2B受体上表现出显著较少或无激动剂活性。本发明的化合物包括式I和药学上可接受的盐、酯和溶剂（包括水合物），其中变量在本规范中定义。
• Dupin,C.; Fraisse-Jullien,R., Bulletin de la Societe Chimique de France, 1964, p. 1993 - 2000
  作者：Dupin,C.、Fraisse-Jullien,R.

  DOI：——

  日期：——
• Chemical and Biological Properties of Some Aminomethyl-2-phenylcyclopropane Derivatives. Pharmacological Comparison with Tranylcypromine
  作者：Uberto M. Teotino、Davide Della. Bella、Arnaldo. Gandini、Giancarlo. Benelli

  DOI：10.1021/jm00318a024

  日期：1967.11