2-Amino-3,3-diphenyl-1-cyclopentene-1-carbonitrile | 3597-67-9

• 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: 2-Amino-3,3-diphenyl-1-cyclopentene-1-carbonitrile
• 英文别名: 2-amine-3,3-diphenylcyclopent-1-enecarbonitrile；2-amino-3,3-diphenyl-cyclopent-1-enecarbonitrile；2-Amino-3,3-diphenyl-cyclopent-1-encarbonitril；2-Amino-3,3-diphenylcyclopent-1-ene-1-carbonitrile；2-amino-3,3-diphenylcyclopentene-1-carbonitrile
• CAS: 3597-67-9
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: LXKLQFKERWNHHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Amino-3,3-diphenyl-1-cyclopentene-1-carbonitrile 在 氢氧化钾 、 硫酸 、 乙二醇 作用下， 生成 2,2-diphenyl-adipic acid dimethyl ester
  参考文献：
  名称：

  Salmon-Legagneur; Neveu, Bulletin de la Societe Chimique de France, 1956, p. 929,936

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯乙腈 在 sodium amide 、 sodium t-butanolate 作用下， 生成 2-Amino-3,3-diphenyl-1-cyclopentene-1-carbonitrile
  参考文献：
  名称：

  The Synthesis of 2,2-Diphenylcyclopentanone and Some of its Derivatives

  摘要：

  DOI：

  10.1021/ja01099a035

文献信息

• Synthesis, Biological Evaluation, and Docking Studies of Tetrahydrofuran- Cyclopentanone- and Cyclopentanol-Based Ligands Acting at Adrenergic α₁- and Serotonine 5-HT_1A Receptors
  作者：Adolfo Prandi、Silvia Franchini、Leda Ivanova Manasieva、Paola Fossa、Elena Cichero、Gabriella Marucci、Michela Buccioni、Antonio Cilia、Lorenza Pirona、Livio Brasili

  DOI：10.1021/jm200421e

  日期：2012.1.12

  A series of aralkylphenoxyethylamine and aralkylmethoxyphenylpiperazine compounds was synthesized and their in vitro pharmacological profile at both 5-HT1A receptors and alpha(1)-adrenoceptor subtypes was measured by binding assay and functional studies. The results showed that the replacement of the 1,3-dioxolane ring by a tetrahydrofuran, cyclopentanone, or cyclopentanol moiety leads to an overall reduction of in vitro affinity at the alpha(1)-adrenoceptor while both potency and efficacy were increased at the 5-HT1A receptor. A significant improvement of 5-HT1A/alpha 1 selectivity was observed in some of the cyclopentanol derivatives synthesized (4a cis, 4c cis and trans). Compounds 2a and 4c cis emerged as novel and interesting 5-HT1A receptor antagonist (pK(i) = 8.70) and a 5-HT1A receptor partial agonist (pK(i) = 9.25, pD(2) = 9.03, E-max = 47%, 5-HT1A/alpha 1a = 69), respectively. Docking studies were performed at support of the biological data and to elucidate the molecular basis for 5-HT1A agonism/antagonism activity.
• (R)-(−)-2,2-DIPHENYLCYCLOPENTANOL
  作者：Denmark, Scott E.、Marcin, Lawrence R.、Schnute, Mark E.、Thorarensen, Atli

  DOI：10.15227/orgsyn.074.0033

  日期：——
• Salmon-Legagneur, Bulletin de la Societe Chimique de France, 1956, p. 411,416
  作者：Salmon-Legagneur

  DOI：——

  日期：——
• Nitroalkene Inter [4 + 2]/Intra [3 + 2] Tandem Cycloadditions. 7. Application of (R)-(-)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary
  作者：Scott E. Denmark、Mark E. Schnute、Lawrence R. Marcin、Atli Thorarensen

  DOI：10.1021/jo00115a042

  日期：1995.5

  Chiral enol ethers derived from (R)-(-)-2,2-diphenylcyclopentanol ((-)-3) have been found to provide high levels of asymmetric induction in tandem inter [4 + 2]/intra [3 + 2] nitroalkene cycloadditions. The chiral auxiliary (>97% ee) is readily prepared in three steps from diphenylacetonitrile employing an asymmetric oxazaborolidine-catalyzed borane reduction. Either enantiomeric series of tandem cycloaddition/hydrogenolysis product 7 is available from the chiral auxiliary of a single absolute configuration by judicious selection of the Lewis acid promoter, Ti(O-i-Pr)(2)Cl-2 (98% ee, (-)-7) or MAPh (93% ee, (+)-7). Propenyl ethers derived from (-)-3 undergo endo selective [4 + 2] cycloadditions (2.3/1 - 8.2/1) in the presence Ti(O-i-Pr)(2)Cl-2; however, exo selective [4 + 2] cycloadditions (10.2/1 - 54.8/1) are observed in the presence of MAPh.
• Salmon-Legagneur; Neveu, Bulletin de la Societe Chimique de France, 1956, p. 929,936
  作者：Salmon-Legagneur、Neveu

  DOI：——

  日期：——