2-phenethylcyclopentanol | 76928-28-4

• 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-phenethylcyclopentanol
• 英文别名: Opt.-inakt. 2-Hydroxy-1-phenaethyl-cyclopentan；2-Phenaethyl-cyclopentanol；2-(2-Phenylethyl)cyclopentan-1-ol
• CAS: 76928-28-4
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: TVRAPNCDYRTYRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenethylcyclopentanol 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到2,3,3a,4,5,9b-Hexahydro-1H-benzoindene
  参考文献：
  名称：

  [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE
  [FR] AGONISTES DE RÉCEPTEUR 5-HT2C ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION

  摘要：

  在某些实施例中提供了一些符合本文所定义的A式化合物，其调节5-HT2C受体的活性。在某些实施例中还提供了一些方法，例如用于体重管理、诱导饱腹感、减少食物摄入，以及预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病理性赌博、奖赏缺乏综合征和性成瘾，强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲症），睡眠障碍（包括失眠、睡眠结构碎裂和慢波睡眠紊乱），尿失禁，精神障碍（包括精神分裂症、厌食症和暴食症），阿尔茨海默病，性功能障碍，勃起功能障碍，癫痫，运动障碍（包括帕金森病和抗精神病药物引起的运动障碍），高血压，血脂异常，非酒精性脂肪肝病，肥胖相关肾脏疾病和睡眠呼吸暂停症。

  公开号：

  WO2017023679A1
• 作为产物：
  描述：

  2-(2-苯基乙基)环戊烷-1-酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以96%的产率得到2-phenethylcyclopentanol
  参考文献：
  名称：

  [EN] 5-HT2C RECEPTOR AGONISTS AND COMPOSITIONS AND METHODS OF USE
  [FR] AGONISTES DE RÉCEPTEUR 5-HT2C ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION

  摘要：

  在某些实施例中提供了一些符合本文所定义的A式化合物，其调节5-HT2C受体的活性。在某些实施例中还提供了一些方法，例如用于体重管理、诱导饱腹感、减少食物摄入，以及预防和治疗肥胖、抗精神病药物引起的体重增加、2型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病理性赌博、奖赏缺乏综合征和性成瘾，强迫症谱系障碍和冲动控制障碍（包括咬指甲和咬甲症），睡眠障碍（包括失眠、睡眠结构碎裂和慢波睡眠紊乱），尿失禁，精神障碍（包括精神分裂症、厌食症和暴食症），阿尔茨海默病，性功能障碍，勃起功能障碍，癫痫，运动障碍（包括帕金森病和抗精神病药物引起的运动障碍），高血压，血脂异常，非酒精性脂肪肝病，肥胖相关肾脏疾病和睡眠呼吸暂停症。

  公开号：

  WO2017023679A1

文献信息

• Electroorganic chemistry. 98. Novel intramolecular stereoselective addition of electrogenerated radical species to the aromatic ring
  作者：Tatsuya. Shono、Naoki. Kise、Takeshi. Suzumoto、Toshio. Morimoto

  DOI：10.1021/ja00275a084

  日期：1986.7

  La reduction electrochimique de derives de l'aryl-5 pentanone-2 conduit a des derives de l'(hexahydro-1,2,3,4,6,8a methyl-1) naphtol-1

  La 还原电化学 de 衍生 de l'aryl-5 pentanone-2 导管 a des 衍生 de l'(hexahydro-1,2,3,4,6,8amethyl-1)naphtol-1
• 5-HT2C receptor agonists and compositions and methods of use
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US10272094B2

  公开（公告）日：2019-04-30

  Provided in some embodiments are compounds of Formula A, as defined herein, that modulate the activity of 5-HT2C receptor. Also provided in some embodiments are methods, such as, for weight management, inducing satiety, and decreasing food intake, and for preventing and treating obesity, antipsychotic-induced weight gain, type 2 diabetes, Prader-Willi syndrome, tobacco/nicotine dependence, drug addiction, alcohol addiction, pathological gambling, reward deficiency syndrome, and sex addiction), obsessive-compulsive spectrum disorders and impulse control disorders (including nail-biting and onychophagia), sleep disorders (including insomnia, fragmented sleep architecture, and disturbances of slow-wave sleep), urinary incontinence, psychiatric disorders (including schizophrenia, anorexia nervosa, and bulimia nervosa), Alzheimer disease, sexual dysfunction, erectile dysfunction, epilepsy, movement disorders (including parkinsonism and antipsychotic-induced movement disorder), hypertension, dyslipidemia, nonalcoholic fatty liver disease, obesity-related renal disease, and sleep apnea.

  在一些实施方案中，提供了如本文所定义的式 A 化合物，其可调节 5-HT2C 受体的活性。在一些实施方案中还提供了一些方法，例如，用于体重管理、诱导饱腹感和减少食物摄入量，以及预防和治疗肥胖症、抗精神病药诱导的体重增加、2 型糖尿病、普拉德-威利综合征、烟草/尼古丁依赖、药物成瘾、酒精成瘾、病态赌博、奖赏缺乏综合征和性成瘾）、强迫症谱系障碍和冲动控制障碍（包括咬指甲和嗜睡）、睡眠障碍（包括失眠、睡眠结构破碎和慢波睡眠紊乱）、尿失禁、精神障碍（包括精神分裂症、神经性厌食症和神经性贪食症）、老年痴呆症、性功能障碍、勃起功能障碍、癫痫、运动障碍（包括帕金森病和抗精神病药物诱发的运动障碍）、高血压、血脂异常、非酒精性脂肪肝、肥胖相关性肾病和睡眠呼吸暂停。
• Electroreductive intramolecular coupling of nonconjugated aromatic ketones
  作者：Naoki Kise、Takeshi Suzumoto、Tatsuya Shono

  DOI：10.1021/jo00085a033

  日期：1994.3

  The electroreduction of nonconjugated aromatic ketones gave intramolecularly coupled products. The best result was obtained using an Sn cathode in i-PrOH containing tetraalkylammonium salt as a supporting electrolyte. This reductive cyclization proceeded with remarkable stereoselectivity, and the cis isomer was obtained exclusively. A variety of new bi- and polycyclic compounds were synthesized. The reaction mechanism was studied, and it was suggested that the anion radical generated by one-electron transfer to a carbonyl group attacks an aromatic ring intramolecularly. The choice of counter cation of the anion radical was critical for the reductive cyclization. Other reductive methods employing metal reducing agents were also studied. Reduction with Na in HMPA-THF gave the same cyclized product, though the yield was lower than that with the electroreduction.
• The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1-hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist
  作者：Nicola Arnold、David Beattie、Michelle Bradley、Andrew Brearley、Lyndon Brown、Steven J. Charlton、Robin A. Fairhurst、David Farr、John Fozard、Joe Fullerton、Martin Gosling、Julia Hatto、Diana Janus、Darryl Jones、Lynne Jordan、Christine Lewis、Janet Maas、Clive McCarthy、Mark Mercer、Helen Oakman、Neil Press、Rachel Profit、Friedrich Schuerch、David Sykes、Roger J. Taylor、Alexandre Trifilieff、Andrew Tuffnell

  DOI：10.1016/j.bmcl.2014.06.014

  日期：2014.9

  The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.
• Synthesis of Cyclopentanohydronaphthalenes and Hydrophenanthrenes with Substituents in an Angular Position
  作者：Homer. Adkins、Glenn F. Hager

  DOI：10.1021/ja01177a005

  日期：1949.9