6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-one | 65565-15-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-one
• 英文别名: 6-chloro-3-phenylindanone；3-phenyl-6-chloro-1-indanone；6-chloro-3-phenylindan-1-one；6-Chloro-3-phenyl-indan-1-on；6-chloro-3-phenyl-2,3-dihydroinden-1-one
• CAS: 65565-15-3
• 化学式: C₁₅H₁₁ClO
• 分子量: 242.705
• InChiKey: RGAOXVRFQQHTQY-UHFFFAOYSA-N

物化性质

• 沸点：
  368.5±42.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-one 在 sodium tetrahydroborate 、 甲酸 、 氯化亚砜 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.0h， 生成 齐洛那平
  参考文献：
  名称：

  Enhanced D1 Affinity in a Series of Piperazine Ring Substituted 1-Piperazino-3-Arylindans with Potential Atypical Antipsychotic Activity

  摘要：

  A study of the effect of aromatic substitution on D-1 and D-2 affinity in a series of previously reported trans-1-piperazino-3-phenylindans shows similar structure-activity relationships for the two receptor sites. 6-Substituted derivatives have affinity for both receptors, and 6-chloro- or B-fluoro-substituted derivatives show preference for D-1 receptors. D-1 affinity and selectivity are significantly increased in a series of new piperazine ring substituted derivatives. Potent D-1 and D-2 antagonism in vivo are confined to derivatives with relatively small substituents in the 2-position of the piperazine ring (e.g. 2-methyl, 2,2-dimethyl, 2-spirocyclobutyl or 2-spirocyclopentyl). Consequently, the effect of aromatic substitution is examined in a series of 1-(2,2-dimethylpiperazino)-3-arylindans. All these compounds except the 4-, 5-, 7- and 4'-chlorosubstituted derivatives have potent D-1 affinity (IC50's below 10 nM) and the majority of the compounds antagonize SK&F 38393-induced circling in 6-OHDA-lesioned rats with ED(50) values about 1 mu mol/kg. In vitro all compounds show preference for D-1 receptors, but in vivo they are equally effective as D-1 and D-2 antagonists. The compounds have high affinity for 5-HT2 receptors and selected compounds show high affinity for alpha(1) adrenoceptors. Furthermore, a subgroup consisting of (-)-38, (-)-39, (-)-41, and (-)-54 does not induce catalepsy in rats. These compounds have the potential of being ''atypical'' antipsychotics and have consequently been selected for further studies. The non-receptor-blocking enantiomers are shown to be inhibitors of DA and NE uptake in accordance with previous observations in compounds unsubstituted in the piperazine ring. Two compounds, (+)-38 and (+)-40, block DA uptake with IC50 values below 10 nM. Finally, the observed structure-activity relationships are discussed in relation to previously published pharmacophore models for D-2 and 5-HT2 receptors. It is concluded that the piperazine substituents might induce a different binding mode at the dopamine receptor sites, perhaps only at the D-1 receptor site.

  DOI：

  10.1021/jm00022a004
• 作为产物：
  描述：

  2,5-二氯苯甲腈 在 N-甲基吡咯烷酮 、 硫酸 、 potassium tert-butylate 、 溶剂黄146 作用下， 反应 25.5h， 生成 6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Application of (2-cyanoaryl)arylacetonitriles in cyclization and annulation reactions. Preparation of 3-arylindans, 4-aryl-3,4-dihydronaphthalenes, 4-arylisoquinolines, 1-aminonaphthalenes, and heterocyclic analogues

  摘要：

  DOI：

  10.1021/jo00303a012

文献信息

• [EN] SUCCINATE AND MALONATE SALT OF TRANS-4-(IR,3S)-6-CHLORO-3-PHENYLINDAN-1-YL)-1,2,2-TRIMETHYLPIPERAZINE AND THE USE AS A MEDICAMENT<br/>[FR] SEL DE SUCCINATE ET DE MALONATE DE TRANS-4-((1R,3S)-6-CHLORO-3-PHENYLINDAN-1-YL)-1,2,2-TRIMETHYLPIPERAZINE ET SON UTILISATION EN TANT QUE MEDICAMENT
  申请人：LUNDBECK & CO AS H

  公开号：WO2005016900A1

  公开（公告）日：2005-02-24

  4-((1R,3S)-6-Chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine hydrogen succinate or hadrogen malonat, pharmaceutical compositions containing these salts and the medical use thereof, including for the treatment of schizophrenia and other psychotic disorders. Also described are methods for the preparation of 4-((1R,3S)-6-Chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and medical uses thereof.

  4-((1R,3S)-6-氯-3-苯基茚-1-基)-1,2,2-三甲基哌嗪氢丁二酸盐或氢丁二酸盐，含有这些盐的药物组合物及其医疗用途，包括用于治疗精神分裂症和其他精神疾病。还描述了制备4-((1R,3S)-6-氯-3-苯基茚-1-基)-1,2,2-三甲基哌嗪和其医疗用途的方法。
• Friedel-crafts cyclisation—VI11Part V.J.M. Allen, K.M. Johnston and R.G. Shotter, Chem. &amp; Ind. 108 (1976).
  作者：J.M. Allen、K.M. Johnston、J.F. Jones、R.G. Shotter

  DOI：10.1016/0040-4020(77)80317-7

  日期：——

  Polyphosphoric acid-catalysed cyclisation of derivatives of crotonophenone and chalcone is shown to be a general reaction which occurs without migration of aryl substituents evident with other Friedel-Crafts catalysts. Two other reactions, however, may intervene: hydrogenation and α-carbonyl cleavage. Thus 4-bromochalcone gives 3 - (p - bromophenyl) -1 - phenylpropan -1 - one, 3 - (p - bromophenyl)indan

  巴豆酮和查尔酮衍生物的多磷酸催化环化反应是一般反应，在没有其他Friedel-Crafts催化剂明显的芳基取代基迁移的情况下发生。但是，可能还会发生另外两个反应：氢化和α-羰基裂解。因此，4-溴查耳酮得到3-（对-溴苯基）-1-苯基丙烷-1-1、3- （对-溴苯基）茚满-1-1和一些苯甲酸。与报道的α，β-不饱和酯和二乙烯基酮环化的机理相比，讨论了环化的机理。中间Wheland配合物的形成被认为是可旋转的。
• DEUTERATED 1-PIPERAZINO-3-PHENYL-INDANES FOR TREATMENT OF SCHIZOPHRENIA
  申请人：JORGENSEN Morten

  公开号：US20120322811A1

  公开（公告）日：2012-12-20

  The present invention relates to deuterated 1-piperazino-3-phenyl-indanes and salts thereof with activity at dopamine receptors D 1 and D 2 as well as the 5HT 2 receptors in the central nervous system, to medicaments comprising such compounds as active ingredients, to the use of such compounds in the treatment of diseases in the central nervous system, and to methods of treatment comprising administration of such compounds.

  本发明涉及氘代1-哌嗪基-3-苯基茚烷及其盐，具有在中枢神经系统中对多巴胺受体D1和D2以及5HT2受体的活性，涉及包含这些化合物作为活性成分的药物、将这些化合物用于治疗中枢神经系统疾病的用途，以及包括给予这些化合物的治疗方法。
• Gold-Catalyzed Carboalkoxylations of 2-Ethynylbenzyl Ethers to form 1- and 2-Indanones Chemoselectively: Effects of Ligands and Solvents
  作者：Chiou-Dong Wang、Yi-Feng Hsieh、Rai-Shung Liu

  DOI：10.1002/adsc.201300988

  日期：2014.1.13

  acidic [tris(pentafluorophenyl)phosphine]gold hexafluoroantimonate [P(C6F5)3AuSbF6] in nitromethane (MeNO2) preferably gives 1‐indanones whereas [(ortho‐biphenyl)di(tert‐butyl)phosphine]gold triflimide [P(tBu)2(o‐biphenyl)AuNTf2] in dichloroethane tends to form 2‐indanone derivatives. For 2‐indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for

  使用合适的催化剂和溶剂，可以从2-乙炔基苄基醚选择性合成1-和2-茚满酮化合物。硝基甲烷（MeNO 2）中的高酸性[三（五氟苯基）膦]六氟锑酸金[P（C 6 F 5）3 AuSbF 6 ]优选产生1-茚满酮，而[（邻-联苯基）二（叔丁基）膦]三氟化金[P（t Bu）2（o-联苯）AuNTf 2]在二氯乙烷中往往会形成2-茚满酮衍生物。对于2-茚满酮产品，我们分离了两个茚基甲基醚进行氘标记分析，为π-炔烃活化提供了证据。
• Indane derivatives, pharmaceutical compositions thereof and method of
  申请人：Kefalas A/S

  公开号：US04443448A1

  公开（公告）日：1984-04-17

  The present invention relates to novel 1-piperazino-3-phenyl-indane derivatives which have pronounced psychopharmacological activity such as neuroleptic activity, analgesic activity, antidepressant activity and, at the same time, a low degree of undesired side-effects, methods for the preparation of said indane derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, such as psychoses and depressions and pain, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.

  本发明涉及一种新型的1-哌嗪-3-苯基-茚衍生物，其具有显著的心理药理活性，如神经阻滞活性、镇痛活性、抗抑郁活性，同时具有低程度的不良副作用，制备该茚衍生物的方法，含有该茚衍生物的制药组合物，以及通过向生物体，包括人类，施加所述衍生物之一的治疗有效量来治疗心理障碍，如精神病和抑郁症和疼痛的方法。