bis(6,11-dihydrodibenzothieopin-11-yl) ether | 1969-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫平类
• 英文名称: bis(6,11-dihydrodibenzothieopin-11-yl) ether
• 英文别名: bis(6,11-dihydrodibenzothiepin-11-yl) ether；di(6,11-dihydrodibenzothiepin-11-yl)ether；Bis-<6,11-dihydro-dibenzothiepin-11-yl>-ether；Bis-(6,11-dihydro-dibenzo[b,e]thiepin-11-yl)-ether；Bis-(6,11-dihydrodibenzo[b,e]thiepin-11-yl) ether；11-(6,11-dihydrobenzo[c][1]benzothiepin-11-yloxy)-6,11-dihydrobenzo[c][1]benzothiepine
• CAS: 1969-25-1
• 化学式: C₂₈H₂₂OS₂
• 分子量: 438.614
• InChiKey: ZMILUZFQQQWEIV-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  580.9±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,11-dihydrodibenzo[b,e]thiepin-11-ol 在 三甲基氯硅烷 、 氰化钠 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 以48%的产率得到bis(6,11-dihydrodibenzothieopin-11-yl) ether
  参考文献：
  名称：

  Sindelar, Karel; Budesinsky, Milos; Vanek, Tomas, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 9, p. 2281 - 2294

  摘要：

  DOI：

文献信息

• Synthesis of the semi-rigid analogues of prothiadene and dithiadene as potential antidepressant and antihistamine agents: 11-[2-(Dimethylaminomethyl)cyclohexylidene]-6,11-dihydrodibenzo[b,e]thiepins and 4-[2-(dimethylaminomethyl)cyclohexylidene]-4,9-dihydrothieno-[2,3-c]-2-benzothiepins
  作者：Zdeněk Polívka、Jiří Holubek、Emil Svátek、Jan Metyš、Miroslav Protiva

  DOI：10.1135/cccc19851078

  日期：——

  Reaction of dibenzo[b,e]thiepin-11(6H)-one with 2-(dimethylaminomethyl)cyclohexylmagnesium chloride gave a mixture of stereoisomeric amino alcohols IX from which four homogeneous bases (IXa to IXd) were separated by chromatography. Dehydration of these compounds with boiling dilute hydrochloric acid afforded mixtures of racemic geometric isomers of the title compound VII, which were separated by crystallization. To the prevailing less polar base VIIa (E)-configuration was assigned on the basis of the IR spectrum. Using a similar procedure, thieno[2,3-c]-2-benzothiepin-4(9H)-one gave mixture of amino alcohols X from which three homogeneous stereoisomers X-A to X-C were isolated. Their dehydration resulted in both expected racemic geometric isomers VIII-A and VIII-B. Pharmacological testing proved the character of an antidepressant for the semi-rigid analogue of dithiadene VIII.

  二苯并[b,e]噻吩-11(6H)-酮与2-(二甲氨基甲基)环己基镁氯化物反应，得到立体异构氨基醇混合物IX，通过色谱法分离出四种均质碱（IXa至IXd）。用沸腾稀盐酸脱水这些化合物，得到标题化合物的外消旋几何异构体混合物VII，通过结晶分离。根据红外光谱，将主要的极性较小的碱VIIa赋予（E）构型。使用类似的程序，噻吩[2,3-c]-2-苯并噻吩-4(9H)-酮得到氨基醇混合物X，从中分离出三种均质立体异构体X-A至X-C。它们的脱水反应产生了预期的外消旋几何异构体VIII-A和VIII-B。药理学测试证明了二硫代二烯的半刚性类似物VIII具有抗抑郁药的特性。
• Carbamates and ureas derived from 11-amino-6,11-dihydrodibenzo[b,e]thiepin; Synthesis and pharmacological screening
  作者：Vladimír Valenta、Marie Bartošová、Miroslav Protiva

  DOI：10.1135/cccc19800517

  日期：——

  A series of N-substituted carbamates V-XIII was prepared by reactions of 6,11-dihydrodibenzo[b,e]thiepin-11-ol (I) with carbamates H₂NCOOR in acetic acid. Whereas the Leuckart reaction of dibenzo[b,e]thiepin-11(6H)-one yielded 9-formamido-10-methylene-9,10-dihydroanthracene (XVIII), a satisfactory method for preparing the amine III was found in heating the carbamate V with 2-aminoethanol to 170°C. Reactions of the amine III with isocyanates gave most of the disubstituted ureas XX-XXV. The expected anticonvulsant activity was found only in high doses with compounds IX, XII, XV, XX, XXI and XXXIII.

  一系列N-取代的氨甲酸酯V-XIII通过在乙酸中6,11-二氢二苯并[be]噻吩-11-醇(I)与氨甲酸酯H2NCOOR反应而制备。而二苯并[be]噻吩-11(6H)-酮的Leuckart反应产生了9-甲酰基-10-亚甲基-9,10-二氢蒽(XVIII)，在加热氨甲酸酯V与2-氨基乙醇至170°C的条件下找到了制备胺III的满意方法。胺III与异氰酸酯反应产生了大部分的二取代脲XX-XXV。预期的抗癫痫活性仅在化合物IX、XII、XV、XX、XXI和XXXIII中高剂量下发现。
• SINDELAR, KAREL;BUDESINSKY, MILOS;VANEK, TOMAS;HOLUBEK, JIRI;SVATEK, EMIL+, COLLECT. CZECHOSL. CHEM. COMMUN., 52,(1987) N 9, 2281-2294
  作者：SINDELAR, KAREL、BUDESINSKY, MILOS、VANEK, TOMAS、HOLUBEK, JIRI、SVATEK, EMIL+

  DOI：——

  日期：——
• Sindelar, Karel; Budesinsky, Milos; Vanek, Tomas, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 9, p. 2281 - 2294
  作者：Sindelar, Karel、Budesinsky, Milos、Vanek, Tomas、Holubek, Jiri、Svatek, Emil、at.al.

  DOI：——

  日期：——