8-甲基硫烷基-2-丙基-3-[[4-[2-(2H-四唑-5-基)苯基]苯基]偏hyl]-1,5,7,9-四氮杂二环[4.3.0]壬-2,5,7-三烯-4-酮 | 168784-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 8-甲基硫烷基-2-丙基-3-[[4-[2-(2H-四唑-5-基)苯基]苯基]偏hyl]-1,5,7,9-四氮杂二环[4.3.0]壬-2,5,7-三烯-4-酮
• 英文名称: biphenanthro<4,3-b;3',4'-d>thiophene
• 英文别名: Diphenanthro[3,4-B:4',3'-D]thiophene；16-thiaheptacyclo[15.12.0.02,15.03,12.04,9.020,29.023,28]nonacosa-1(17),2(15),3(12),4,6,8,10,13,18,20(29),21,23,25,27-tetradecaene
• CAS: 168784-35-8
• 化学式: C₂₈H₁₆S
• 分子量: 384.501
• InChiKey: UNKICAROUFRVIX-UHFFFAOYSA-N

物化性质

• 沸点：
  676.7±24.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二氯二甲基硅烷 、 8-甲基硫烷基-2-丙基-3-[[4-[2-(2H-四唑-5-基)苯基]苯基]偏hyl]-1,5,7,9-四氮杂二环[4.3.0]壬-2,5,7-三烯-4-酮 在 四甲基乙二胺 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 以48%的产率得到9,9-dimethyl-9H-diphenanthro[3,4-b:4’,3’-d]silole
  参考文献：
  名称：

  硫杂[7]螺烯通过芳香变态转化为氮杂[7]螺烯和[7]螺烯类化合物

  摘要：

  [n]具有螺旋扭曲结构的螺旋烯由于其独特的性质而引起了越来越多的兴趣。因此，开发能够获得多种[n]螺旋烯的简便合成方法一直是一个重要问题。在这里，我们报告了以硫杂[7] 螺旋烯为常见原料合成[7] 螺旋烯和[7] 螺旋烯类化合物。硫杂[7]螺烯的脱硫二锂化以及随后与硅和磷亲电子试剂的反应分别得到了噻咯和磷烯稠合的[7]螺烯类化合物。环戊二烯稠合的[7]类螺烯化合物和吡咯稠合的氮杂[7]螺烯也分别通过硫杂[7]螺烯S,S-二氧化物与碳和氮亲核试剂的双重SNAr反应成功合成。thia[7]helicene S, 与母体硫杂[7]螺烯相比，二氧化硫的吸收光谱略有红移，理论计算很好地证明了这一点。silole-稠合[7]类螺烯化合物的硅原子上的取代基对最长吸收最大值影响不大。对于环戊二烯稠合的[7]类螺烯化合物和氮杂[7]螺烯，也观察到取代基对吸收性能的影响很小，并且通过理论计算得到了很好的证明。thia[7]helicene

  DOI：

  10.3390/molecules27030606
• 作为产物：
  描述：

  3,3'-dihydroxy-4,4'-biphenanthryl 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 8-甲基硫烷基-2-丙基-3-[[4-[2-(2H-四唑-5-基)苯基]苯基]偏hyl]-1,5,7,9-四氮杂二环[4.3.0]壬-2,5,7-三烯-4-酮
  参考文献：
  名称：

  Synthesis of Structurally Modified Atropisomeric Biaryl Dithiols. Observations on the Newman-Kwart Rearrangement

  摘要：

  The preparation of a number of biaryldithiols from biaryldiols is discussed. A key reaction is the Newman-Kwart thermorearrangement of bisthiocarbamates and crucial variables of temperature and reaction time have been identified. Alternative approaches to 3,3'-disubstituted dithiols via ortho metallation are presented, The benefit of using such disubstituted compounds is illustrated with representative examples of the stereochemical features of the derived carbanions in reactions with prochiral electrophiles. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00268-8

文献信息

• New axially chiral sulfur compounds: Synthesis and conformational stability of enantiopure 4,4′-biphenanthrene-3,3′-dithiol and related atropisomeric derivatives
  作者：Antonio Dore、Davide Fabbri、Serafino Gladiali、Giovanni Valle

  DOI：10.1016/0957-4166(95)00074-y

  日期：1995.3

  Enantiopure (R)- and (S)-4,4'-biphenanthrene-3,3'-dithiol la has been prepared for the first time through a synthetic procedure involving in the key step a stereoconservative Newman-Kwart thermorearrangement of the bis-N,N-dimethylthiocarbamoyl ester of(R)- and (S)-biphenanthrol 2b, respectively. The atropisomeric conformations of la are not interconverted even at temperatures as high as 285 degrees C, whereas the related biphenanthrothiophene 3 is completely racemized in a few minutes at 250 degrees C. The axially chiral backbone of la has been incorporated in a set of novel C-2 symmetry sulfur reagents suitable for a variety of stereoselective reactions.
• Synthesis of Structurally Modified Atropisomeric Biaryl Dithiols. Observations on the Newman-Kwart Rearrangement
  作者：Sergio Cossu、Ottorino De Lucchi、Davide Fabbri、Giovanni Valle、Gavin F. Painter、Robin A.J. Smith

  DOI：10.1016/s0040-4020(97)00268-8

  日期：1997.4

  The preparation of a number of biaryldithiols from biaryldiols is discussed. A key reaction is the Newman-Kwart thermorearrangement of bisthiocarbamates and crucial variables of temperature and reaction time have been identified. Alternative approaches to 3,3'-disubstituted dithiols via ortho metallation are presented, The benefit of using such disubstituted compounds is illustrated with representative examples of the stereochemical features of the derived carbanions in reactions with prochiral electrophiles. (C) 1997 Published by Elsevier Science Ltd.
• Transformation of Thia[7]helicene to Aza[7]helicenes and [7]Helicene-like Compounds via Aromatic Metamorphosis
  作者：Keisuke Uematsu、Chikara Hayasaka、Ko Takase、Keiichi Noguchi、Koji Nakano

  DOI：10.3390/molecules27030606

  日期：——

  cyclopentadiene-fused [7]helicene-like compounds and aza[7]helicenes and was well demonstrated by the theoretical calculations. The thia[7]helicene S,S-dioxide and the silole-fused [7]helicene-like compound exhibited bright blue emission, and the cyclopentadiene-fused [7]helicene-like compound and the aza[7]helicenes showed strong violet emission. Each single enantiomer of the aza[7]helicenes showed circularly-polarized

  [n]具有螺旋扭曲结构的螺旋烯由于其独特的性质而引起了越来越多的兴趣。因此，开发能够获得多种[n]螺旋烯的简便合成方法一直是一个重要问题。在这里，我们报告了以硫杂[7] 螺旋烯为常见原料合成[7] 螺旋烯和[7] 螺旋烯类化合物。硫杂[7]螺烯的脱硫二锂化以及随后与硅和磷亲电子试剂的反应分别得到了噻咯和磷烯稠合的[7]螺烯类化合物。环戊二烯稠合的[7]类螺烯化合物和吡咯稠合的氮杂[7]螺烯也分别通过硫杂[7]螺烯S,S-二氧化物与碳和氮亲核试剂的双重SNAr反应成功合成。thia[7]helicene S, 与母体硫杂[7]螺烯相比，二氧化硫的吸收光谱略有红移，理论计算很好地证明了这一点。silole-稠合[7]类螺烯化合物的硅原子上的取代基对最长吸收最大值影响不大。对于环戊二烯稠合的[7]类螺烯化合物和氮杂[7]螺烯，也观察到取代基对吸收性能的影响很小，并且通过理论计算得到了很好的证明。thia[7]helicene