6H,12H-Dibenzo<1,5>dithiocin | 263-06-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6H,12H-Dibenzo<1,5>dithiocin
• 英文别名: 1,5-dibenzodithiocin；6H,12H-dibenzo-1,5-dithiocin；6h,12h-Diben-zo[b,f][1,5]dithiocine；6,12-dihydrobenzo[c][1,5]benzodithiocine
• CAS: 263-06-9
• 化学式: C₁₄H₁₂S₂
• 分子量: 244.381
• InChiKey: GVKYAFCSGQZUNK-UHFFFAOYSA-N

物化性质

• 沸点：
  404.5±45.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)
• 熔点：
  74.0-76.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6H,12H-Dibenzo<1,5>dithiocin 在 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到6H,12H-dibenzo-1,5-dithiocin disulfoxide
  参考文献：
  名称：

  Chemistry of sulfenic acids. 5. A novel rearrangement of 2,4,6-trineopentylbenzenesulfenic acid to 2-tert-butyl-4,6-dineopentylbenzo[b]thiete and 3,3-dimethyl-4,4-dihydro-6,8-dineopentylbenzo[b]thiopyran. Synthesis of thiete sulfoxides

  摘要：

  DOI：

  10.1021/jo00166a028
• 作为产物：
  描述：

  硫代色满 1000.0 ℃ 、0.0 Pa 条件下， 生成 6H,12H-Dibenzo<1,5>dithiocin
  参考文献：
  名称：

  The syntheses of 6-methylene-2,4-cyclohexadien-1-imine and related o-quinonoids by FVT of 1-hetero-1,2,3,4-tetrahydronaphthalenes

  摘要：

  Flash vacuum thermolysis (almost-equal-to 1000-degrees-C/10(-5) hPa) of 1,2,3,4-tetrahydroquinoline, chroman, and thiochroman, led upon loss of ethylene (retro-Diels-Alder reaction) to the o-quinonoids 1-3. These reactive monomers were identified by IR-UV at -196-degrees-C and/or MS/MS.

  DOI：

  10.1016/s0040-4039(00)78895-2

文献信息

• Cycloaddition reactions of 2<i>H</i>-benzo[<i>b</i>]thiete and conjugated cyclic dienes
  作者：Dieter Gröschl、Herbert Meier

  DOI：10.1002/jhet.5570330630

  日期：1996.11

  2H-Benzo[b]thiete 1 reacts with cyclopentadiene 3 in consecutive [8π + 2π]cycloadditions yielding the condensed heterocycles 6–8. Tetracyclone 9 on the other hand gives only the monoadduct 10. An [8π + 8π]cycloaddition can be observed for 1 and diphenylisobenzofuran 11. The related π system 13 shows again consecutive [477π + 27π]processes (1 + 13 ← 14, 15).

  2 H-苯并[ b ]硫杂环丁烷1在连续的[8π+2π]环加成反应中与环戊二烯3反应，生成稠合杂环6-8。另一方面，四旋风分离器9仅给出单加合物10。可以观察到1和二苯基异苯并呋喃11的[8π+8π]环加成反应。相关的π系统13再次示出了连续的[477π+27π]过程（1 + 13←14、15）。
• Stereoselective Synthesis of Polycyclic Thiopyrans
  作者：Herbert Meier、Michael Schmidt、Axel Mayer、Dieter Schollmeyer、Bernhard Beile

  DOI：10.1002/jhet.789

  日期：2012.5

  The reaction of benzothiete (1) and the bicyclic alkenes 5, 7, 9, or 12 shows a very high π side selectivity (de > 95%) in the formation of the polycyclic thiopyrans 6, 8, 10, 11, 13, and 14.

  benzothiete的反应（1）和双环烯烃5，7，9，或12示出了在多环噻喃的形成非常高的π侧选择性的（de> 95％）6，8，10，11，13，和14。
• Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Synthesis of 11-(dimethylaminoalkyl) derivatives of 11H-dibenzo[b,e]-1,4-dioxepin and 11H-dibenzo[b,e]-1,4-dithiepin
  作者：Karel Šindelář、Jiří Holubek、Miroslav Ryska、Emil Svátek、Antonín Dlabač、Marta Hrubantová、Miroslav Protiva

  DOI：10.1135/cccc19820072

  日期：——

  1-[2-(2-Fluorophenoxy)phenyl]-4-dimethylaminobutanol (XI) was synthesized from 2-(2-fluorophenoxy)benzoic acid (VIII) in three steps and cyclized with sodium hydride in dimethylformamide to the title compound V. Reaction of 5-chloro-2-(methylthio)thiophenol (XIV) with sodium and liquid ammonia afforded benzene-1,2-dithiol (XIII) which was treated with 2-bromobenzyl bromide and gave 11H-dibenzo[b,e]-1,4-dithiepin (II). An alternative synthesis of compound II consisted in the cyclization of 2-(2-bromophenylthiomethyl)thiophenol (XVIII) and was accompanied by the simultaneous formation of 6H, 12H-dibenzo[b,f]-1,5-dithiocin (XIX) and thianthrene (XX). Reaction of compound II with n-butyllithium and the following treatment with dimethylaminoalkyl chlorides or with carbon dioxide resulted on the one hand in two further title compounds VI and VII, and in the carboxylic acid XXI on the other. 2-Chloro-11H-dibenzo[b,e]-1,4-dithiepin (XXII) was obtained by a further synthesis alternative using in the first step the cyclization of 2-(4-chloro-2-chloromethylphenylthio)thiophenol (XXV). Compound VI and VII showed a high degree of activity in the test of antagonization of reserpine hypothermia in mice.

  1-[2-(2-氟苯氧基)苯基]-4-二甲氨基丁醇（XI）是从2-(2-氟苯氧基)苯甲酸（VIII）经过三个步骤合成，并在二甲基甲酰胺中与氢化钠环化得到了标题化合物V。5-氯-2-(甲硫基)噻吩酚（XIV）与钠和液氨反应生成苯-1,2-二硫醚（XIII），然后与2-溴苄溴化物反应生成11H-二苯并[b,e]-1,4-二硫杂环戊烷（II）。化合物II的另一种合成方法是通过2-(2-溴苯硫甲基)噻吩酚（XVIII）环化，同时伴随生成6H, 12H-二苯并[b,f]-1,5-二硫杂环辛烷（XIX）和硫蒽（XX）。化合物II与正丁基锂反应，随后处理与二甲基氨基烷氯化物或二氧化碳，一方面生成另外两种标题化合物VI和VII，另一方面生成羧酸XXI。通过另一种合成方法，首先使用2-(4-氯-2-氯甲基苯基硫)噻吩酚（XXV）环化，得到2-氯-11H-二苯并[b,e]-1,4-二硫杂环辛（XXII）。化合物VI和VII在小鼠对去甲肾上腺素低温症的拮抗试验中表现出很高的活性。
• Cycloaddition reactions of benzothiete and hetero dienophiles for the synthesis of heterocyclic systems
  作者：Dominic Jacob、Hans Peter-Niedermann、Herbert Meier

  DOI：10.1016/s0040-4039(00)85305-8

  日期：——

  Benzothiete () undergoes cycloaddition reactions with hetero dienophiles with NN-, NO- or CO- double bonds, leading to six-membered heterocyclic ring systems of 2H-3,4-dihydro-1,2,3-benzothiadiazine (), 4H-3,1,2-benzoxathiazine () and 4H-3,1-benzoxathiin.

  苯并噻吩（）与具有NN-，NO-或CO-双键的杂二烯亲二烯体进行环加成反应，形成2H-3,4-二氢-1,2,3-苯并噻二嗪的六元杂环系统（），4H- 3,1,2-苯并恶嗪（）和4H-3,1-苯并恶嗪。
• Schmidt, Michael; Meier, Herbert; Niedermann, Hans-Peter, Chemische Berichte, 1990, vol. 123, # 5, p. 1143 - 1148
  作者：Schmidt, Michael、Meier, Herbert、Niedermann, Hans-Peter、Mengel, Rudolf

  DOI：——

  日期：——