5,5′-bis(trimethylsilyl)-(3,3′-bithiophene)-2,2′-dicarbaldehyde | 1465758-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5′-bis(trimethylsilyl)-(3,3′-bithiophene)-2,2′-dicarbaldehyde
• 英文别名: 5,5′-di(trimethylsilyl)-3,3′-bithiophenyl-2,2′-dicarbaldehyde；3-(2-Formyl-5-trimethylsilylthiophen-3-yl)-5-trimethylsilylthiophene-2-carbaldehyde；3-(2-formyl-5-trimethylsilylthiophen-3-yl)-5-trimethylsilylthiophene-2-carbaldehyde
• CAS: 1465758-99-9
• 化学式: C₁₆H₂₂O₂S₂Si₂
• 分子量: 366.652
• InChiKey: SMEKOHGTAPKQOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5′-bis(trimethylsilyl)-(3,3′-bithiophene)-2,2′-dicarbaldehyde 、 对甲苯磺酰肼 以 四氢呋喃 为溶剂， 以100%的产率得到N',N''-((5,5'-bis(trimethylsilyl)-[3,3'-bithiophene]-2,2'-diyl)bis(methanylylidene))bis(4-methylbenzenesulfonylhydrazone)
  参考文献：
  名称：

  Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applications

  摘要：

  The use of CuTC (Liebeskind's catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This approach establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer, which has previously been underused in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

  DOI：

  10.1055/s-0033-1340667
• 作为产物：
  描述：

  3-溴噻吩-2-甲醛 在 正丁基锂 、 噻吩-2-甲酸亚铜(I) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 正己烷 、 甲苯 为溶剂， 反应 78.67h， 生成 5,5′-bis(trimethylsilyl)-(3,3′-bithiophene)-2,2′-dicarbaldehyde
  参考文献：
  名称：

  Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applications

  摘要：

  The use of CuTC (Liebeskind's catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This approach establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer, which has previously been underused in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.

  DOI：

  10.1055/s-0033-1340667

文献信息

• Syntheses and Crystal Structures of 2,7-Di(trimethylsilyl)thieno[3,2-<i>e</i>]benzothiophene, 1,2,5,6(5)-Tetra(trimethylsilyl)-1,2,5,6(2,3)-tetrathiophenacyclooctaphan-3(<i>z</i>),7(<i>z</i>)-diene, and 2,7-Di(trimethylsilyl)thieno[3,2-<i>e</i>]benzothiophene-4-ol
  作者：Zhihua Wang、Jianwu Shi、Xinyong Tian、Li Xu、Chunli Li、Hua Wang

  DOI：10.1002/jhet.1100

  日期：2013.7

  as precusor, 2,7‐di(trimethylsilyl)‐thieno[3,2‐e]benzothiophene was obtained effiently via intramolecular McMurry reaction. At the same time, another two unexpected compounds, 1,2,5,6(5)‐tetra‐(trimethylsilyl)‐1,2,5,6(2,3)‐tetrathiophena‐cyclooctaphan‐3(Z),7(Z)‐diene and 2,7‐di(trimethylsilyl)thieno[3,2‐e]‐benzothiophene‐4‐ol were generated as side products. The crystal structures of all three title

  以5,5'-二（三甲基硅烷基）-3,3'-联硫基苯基-2,2'-二甲醛为先驱物，通过分子内有效地获得了2,7-二（三甲基硅烷基）-噻吩并[3,2- e ]苯并噻吩麦克默里反应。同时，另外两个意外化合物1,2,5,6（5）-四-（三甲基甲硅烷基）-1,2,5,6（2,3）-四噻吩-环辛烷3（Z），7 （Z）-二烯和2,7-二（三甲基甲硅烷基）噻吩并[3,2 - e ]-苯并噻吩-4-醇是副产物。描述了所有三种标题化合物的晶体结构。
• Comparison of Ullmann/RCM and Ullmann/Bis-hydrazone Coupling Reactions; New Access to Benzodithiophenes for Dye-Sensitized Solar Cell and Thiahelicene Applications
  作者：G. Stephenson、Silvia Cauteruccio、Julien Doulcet

  DOI：10.1055/s-0033-1340667

  日期：——

  The use of CuTC (Liebeskind's catalyst), followed by methylenation and ring-closing metathesis, or bis-hydrazone coupling reactions is described. This approach establishes an alternative non-photochemical synthesis of the strategically important 1,2-b:4,3-b' BDT regioisomer, which has previously been underused in applications such as dye-sensitized solar cells and nonlinear optics because of the difficulty of synthesis on a large scale.