3,14-difluoro-8,19-bis(trifluoromethyl)tetrabenzodithiepino<4,5-b;4',5'-f>-1,5-dioxocin-11,22-dione | 77795-65-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,14-difluoro-8,19-bis(trifluoromethyl)tetrabenzodithiepino<4,5-b;4',5'-f>-1,5-dioxocin-11,22-dione
• 英文别名: 3,14-difluoro-8,19-bis(trifluoromethyl)tetrabenzo[a,d,j,m]dithiepino[4,5-b;4',5'-f]-1,5-dioxocin-11,22-dione；8,25-difluoro-15,32-bis(trifluoromethyl)-2,19-dioxa-11,28-dithiaheptacyclo[19.13.0.04,18.05,10.012,17.022,27.029,34]tetratriaconta-1(21),4(18),5(10),6,8,12(17),13,15,22(27),23,25,29(34),30,32-tetradecaene-3,20-dione
• CAS: 77795-65-4
• 化学式: C₃₂H₁₂F₈O₄S₂
• 分子量: 676.564
• InChiKey: UKCMVUREPXZSRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.64
• 重原子数：
  46.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.42
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  methyl <4-fluoro-2-(4-trifluoromethyl-2-methoxycarbonylphenylthio)phenyl>acetate 生成 3,14-difluoro-8,19-bis(trifluoromethyl)tetrabenzodithiepino<4,5-b;4',5'-f>-1,5-dioxocin-11,22-dione
  参考文献：
  名称：

  SINDELAR K.; RYSKA M.; HOLUBEK J.; SVATEK E.; METYSOVA J.; PROTIVA J.; PR+, COLLECT. CZECH. CHEM. COMMUN., 1981, 46, NO 1, 118-140

  摘要：

  DOI：

文献信息

• Fluorinated tricyclic neuroleptics with prolonged action: 3-Fluoro-8-trifluoromethyl derivatives of 10-(4-methylpiperazino)- and 10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrodibenzo-[b,f]thiepin
  作者：Karel Šindelář、Miroslav Ryska、Jiří Holubek、Emil Svátek、Jiřina Metyšová、Jiří Protiva、Miroslav Protiva

  DOI：10.1135/cccc19810118

  日期：——

  A reaction of (4-fluoro-2-iodophenyl)acetic acid with 4-(trifluoromethyl)thiophenol gave the acid VIII which was cyclized with the reagent consisting from methanesulphonic acid and phosphorus pentoxide and afforded the methanesulphonic enol ester XIX. The alkaline hydrolysis resulted in 3-fluoro-8-trifluoromethyldibenzo[b,f]thiepin-10(11H)-one (XVI) which was transformed via the alcohol XXIV to the chloro derivative XXV. Substitution reactions with 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine resulted in the title compounds IV and V. These products are very potent cataleptic neuroleptic agents with a prolongation of duration of the effects comparable to that of isofloxythepin and tefluthixol. A series of further synthetic experiments aimed at alternative syntheses of the acid VIII and the ketone XVI; their results were mostly not of use for preparative purpose but they led to isolation and characterization of a series of interesting heterocyclic products (XVII, XVIII, XXII, XXIII, XXIX-XXXI, XXXVI-XXXIX).

  (4-氟-2-碘苯基)乙酸与4-(三氟甲基)硫代苯酚反应，生成酸VIII，然后与由甲磺酸和五氧化二磷组成的试剂环化，生成甲磺酸烯基酯XIX。碱性水解产生3-氟-8-三氟甲基二苯并[bf]噻吩-10(11H)-酮(XVI)，通过醇XXIV转化为氯衍生物XXV。与1-甲基哌嗪和1-(2-羟乙基)哌嗪的取代反应产生IV和V。这些产物是非常有效的猫病性镇静剂，其效果持续时间延长，与异氟沙替平和替氟西乐相当。一系列进一步的合成实验旨在寻找酸VIII和酮XVI的替代合成方法；它们的结果大多数并没有用于制备目的，但导致了一系列有趣的杂环产物(XVII、XVIII、XXII、XXIII、XXIX-XXXI、XXXVI-XXXIX)的分离和表征。