3-trifluoro-methylthio-5H-dibenzo[a,d]cyclohepten-5-one | 63418-31-5

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 3-trifluoro-methylthio-5H-dibenzo[a,d]cyclohepten-5-one
• 英文别名: 3-<(trifluoromethyl)thio>-5H-dibenzocyclohepten-5-one；3-trifluoromethylthio-5H-dibenzo[a,d]cyclohepten-5-one；3-Trifluormethylthio-5H-dibenzocyclophepten-5-on；3-Trifluormethylthio-5H-dibenzo[a,d]cyclophepten-5-on；5-(Trifluoromethylsulfanyl)tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-one
• CAS: 63418-31-5
• 化学式: C₁₆H₉F₃OS
• 分子量: 306.308
• InChiKey: ZPJBZIPPEYYPPI-UHFFFAOYSA-N

物化性质

• 沸点：
  353.1±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-trifluoro-methylthio-5H-dibenzo[a,d]cyclohepten-5-one 在 二氯乙酸 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 3-<(trifluoromethyl)thio>-5-methyl-5-(hydroxyamino)-5H-dibenzocycloheptene
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a series of dibenzo[a,d]cycloalkenimines as N-methyl-D-aspartate antagonists

  摘要：

  A series of 73 dibenzo[a,d]cycloalkenimines were synthesized and evaluated for their ability to displace (+)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine ([3H]-(+)-10) from its specific binding site on rat cortical membranes. A number of the more active compounds (Ki ranging from 0.006 to 0.21 microM) were evaluated for N-methyl-D-aspartate (NMDA) antagonist activity in the rat cortical slice (Kb ranging from 0.08 to 0.9 microM) and anticonvulsant activity in the mouse against NMDA induced convulsions. The ED50 values ranged from 0.22 to 7.76 mg/kg and correlated reasonably well with the Kb determination. In the dibenzo[a,d]cyclohepten-5,10-imine series, the (+)-5S,10R enantiomer displayed consistently higher levels of biological activity. While substitution at the 3-position of (+)-10 with electronegative atoms generally increased in vitro activity, a loss of potency relative to (+)-10 (MK-801) was observed in vivo for all of the compounds tested.

  DOI：

  10.1021/jm00164a052
• 作为产物：
  描述：

  3-bromo-5H-dibenzo[a,d]cyclohepten-5-one 、 mercury bis(trifluoromethanethiolate) 生成 3-trifluoro-methylthio-5H-dibenzo[a,d]cyclohepten-5-one
  参考文献：
  名称：

  （-）-1-环丙基甲基-4-（3-三氟甲硫基-5H-二苯并[a，d]环庚-5-亚基）哌啶的合成和立体定向抗精神病活性。

  摘要：

  3-碘正庚庚啶[（+/-）-5a]和1-环丙基甲基-4-（3-碘-5H-二苯并[a，d]环庚-5-亚烷基）哌啶[（+/- ）-5b]。所得的阻转异构体与三氟甲基硫代铜反应，得到旋光产物，而没有广泛的外消旋作用。以这种方式，光学上纯的（+）-和（-）-3-三氟甲基硫基庚庚定[分别为（（+）-6a和（-）-6a]]和（+）-和（-）-1-环丙基甲基-4-（已经制备了3-三氟甲硫基-5H-二苯并[a，d]环庚基-5-亚烷基）哌啶[分别为（（+）-6b和（-）-6b]]。讨论了手性euro转移试剂对质子和氟共振信号的影响，作为确定这些阻转异构体光学纯度的诊断工具。（+）-6a，（-）-6a，（+）-6b和（-）-6b这四种化合物，研究了松鼠猴阻止有条件回避反应的能力。发现所有的抗回避活性仅存在于左旋化合物（-）-6a和（-）-6b中。对映异构体（-）-6b和（+）-6b的进一步比较表明，拮抗阿扑吗

  DOI：

  10.1021/jm00218a005

文献信息

• Process for preparing aryl trifluoromethylsulfides
  申请人：Merck & Co., Inc.

  公开号：US04020169A1

  公开（公告）日：1977-04-26

  Trifluoromethylthiocopper, formed in situ by the reaction of bis-(trifluoromethylthio)mercury with copper, reacts with aromatic bromides and iodides to give aryl trifluoromethyl sulfides.

  在反应双(三氟甲硫基)汞和铜的过程中，形成了现场三氟甲基硫基铜，它与芳香族溴化物和碘化物反应，生成芳基三氟甲基硫醚。
• Trifluoromethylthio (and sulfonyl) derivatives of cyproheptadine analogs
  申请人：Merck & Co., Inc.

  公开号：US04031222A1

  公开（公告）日：1977-06-21

  Cyproheptadine derivatives substituted with a trifluoromethylthio or trifluoromethylsulfonyl group in one of the benzo rings and having a hydroxyalkyl or cycloalkylalkyl group on the piperidine nitrogen are potent antipsychotic agents, with a low propensity to induce extrapyramidal side effects that are experienced with most major tranquilizers. The tranquilizing activity is predominantly in the levorotatory enantiomers, whereas the dextrorotatory enantiomers have anticholinergic activity. Each enantiomer is useful as a source of the other by racemization. The novel compounds are prepared by treatment of the corresponding iodo or bromo compound with bis(trifluoromethylthio)mercury and copper powder.

  一种Cyproheptadine衍生物，在其苯环中的一个上取代有三氟甲基硫醇或三氟甲基磺酰基，并在哌啶氮上具有羟基烷基或环烷基烷基，是有效的抗精神病药物，具有引起大多数主要镇静剂经外锥体副作用的低倾向。镇静活性主要在左旋异构体中，而右旋异构体具有抗胆碱能活性。通过消旋反应，每个对映体都可用作另一个对映体的来源。这些新化合物是通过将相应的碘化物或溴化物化合物与双(三氟甲基硫醇)汞和铜粉处理制备的。
• Trifluoromethylthio derivatives of cyproheptadine
  申请人：Merck & Co., Inc.

  公开号：US04031223A1

  公开（公告）日：1977-06-21

  Cyproheptadine derivatives substituted with a trifluoromethylthio group in one of the benzo rings and certain derivatives thereof are potent antipsychotic agents, with a low propensity to induce extrapyramidal side effects experienced with most major tranquilizers, and platelet aggregation inhibitors useful as antithrombotic agents. The antipsychotic activity resides in the levorotatory enantiomer whereas both enantiomers are platelet aggregation inhibitors. The novel compounds are prepared by treatment of the corresponding iodo compound with trifluoromethylthiocopper formed from bis-(trifluoromethylthio)mercury and copper powder.

  一些含有三氟甲基硫基取代苯环的Cyproheptadine衍生物及其某些衍生物是有效的抗精神病药物，具有低诱发大多数主要安定剂引起的锥体外系副作用的倾向，并且是有用的抗血栓药物血小板聚集抑制剂。抗精神病活性存在于左旋异构体中，而两个对映异构体都是血小板聚集抑制剂。新型化合物通过用双（三氟甲基硫基）汞和铜粉形成的三氟甲基硫基铜处理相应的碘化物来制备。
• 3-Trifluoromethylsulfinyl analogs of cyproheptadine, process for their preparation and pharmaceutical composition thereof
  申请人：Merck & Co., Inc.

  公开号：EP0002263A1

  公开（公告）日：1979-06-13

  Cyproheptadine derivatives of formula: or pharmaceutically acceptable salt thereof, wherein: R represents (1) lower alkyl of 1-3 carbons, especially -CH3, or and R' represents hydrogen, lower alkyl of 1-3 carbon atoms, or fluoro, are antipsychotic agents, with a low propensity to induce extrapyramidal side effects that are experienced with most major tranquilizers. Compounds (I) are generally prepared by treatment of the intermediate 5-carbinol with a dehydrating reagent, or by alkylation of the piperidine nitrogen with the appropriate alkyl or substituted alkyl group.

  式中的赛庚啶衍生物 或其药学上可接受的盐，其中 R 代表 (1) 1-3 碳的低级烷基，特别是-CH3、 或 和 R' 代表氢、1-3 个碳原子的低级烷基或氟、 是抗精神病药物，诱发大多数主要镇静剂的锥体外系副作用的倾向性较低。 化合物(I)通常是通过脱水试剂处理 5-甲醇中间体，或用适当的烷基或取代烷基对哌啶氮进行烷基化而制备的。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.2, 6.2.1.6.10, page 251 - 267
  作者：

  DOI：——

  日期：——