3,4-Dibutyl-5-[2-(3,4-dibutyl-5-formylthiophen-2-yl)ethynyl]thiophene-2-carbaldehyde | 1233481-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-Dibutyl-5-[2-(3,4-dibutyl-5-formylthiophen-2-yl)ethynyl]thiophene-2-carbaldehyde
• 英文别名: 3,4-dibutyl-5-[2-(3,4-dibutyl-5-formylthiophen-2-yl)ethynyl]thiophene-2-carbaldehyde
• CAS: 1233481-80-5
• 化学式: C₂₈H₃₈O₂S₂
• 分子量: 470.741
• InChiKey: FIBRSJJQLNHNBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  3,4-Dibutyl-5-[2-(3,4-dibutyl-5-formylthiophen-2-yl)ethynyl]thiophene-2-carbaldehyde 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以15%的产率得到octabutyltetradehydrotetrathia[24]annulene[2.2.2.2]
  参考文献：
  名称：

  McMurry Coupling of Diformyldithienylacetylene: Synthesis of [24]-, [36]-, and [48]Annulenes Composed of Thiophene, Acetylene, and Ethylene Units

  摘要：

  The reaction of diformyldithienylacetylene 4 with a McMurry reagent prepared from TiCl(4), Zn, and pyridine in THF afforded 24 pi-dimer 1b (15%), 36 pi-trimer 2b (13%), and 48 pi-tetramer 3b (6%). From X-ray analysis, 1b adopts a twisted conformation, although the (1)H NMR spectrum of 1b shows a symmetrical structure owing to a rapid conformational change in solution. Absorption and emission spectra, redox properties, and electric conductivities of 1b-3b were measured in order to study the structure-property relationship of these macrocyclic systems.

  DOI：

  10.3987/com-10-s(e)96
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 双(3,4-二丁基-2-噻吩基)乙炔 在 正丁基锂 作用下， 以75%的产率得到3,4-Dibutyl-5-[2-(3,4-dibutyl-5-formylthiophen-2-yl)ethynyl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  McMurry Coupling of Diformyldithienylacetylene: Synthesis of [24]-, [36]-, and [48]Annulenes Composed of Thiophene, Acetylene, and Ethylene Units

  摘要：

  The reaction of diformyldithienylacetylene 4 with a McMurry reagent prepared from TiCl(4), Zn, and pyridine in THF afforded 24 pi-dimer 1b (15%), 36 pi-trimer 2b (13%), and 48 pi-tetramer 3b (6%). From X-ray analysis, 1b adopts a twisted conformation, although the (1)H NMR spectrum of 1b shows a symmetrical structure owing to a rapid conformational change in solution. Absorption and emission spectra, redox properties, and electric conductivities of 1b-3b were measured in order to study the structure-property relationship of these macrocyclic systems.

  DOI：

  10.3987/com-10-s(e)96

文献信息

• McMurry Coupling of Diformyldithienylacetylene: Synthesis of [24]-, [36]-, and [48]Annulenes Composed of Thiophene, Acetylene, and Ethylene Units
  作者：Masahiko Iyoda、Pochi Huang、Tomohiko Nishiuchi、Masayoshi Takase、Tohru Nishinaga

  DOI：10.3987/com-10-s(e)96

  日期：——

  The reaction of diformyldithienylacetylene 4 with a McMurry reagent prepared from TiCl(4), Zn, and pyridine in THF afforded 24 pi-dimer 1b (15%), 36 pi-trimer 2b (13%), and 48 pi-tetramer 3b (6%). From X-ray analysis, 1b adopts a twisted conformation, although the (1)H NMR spectrum of 1b shows a symmetrical structure owing to a rapid conformational change in solution. Absorption and emission spectra, redox properties, and electric conductivities of 1b-3b were measured in order to study the structure-property relationship of these macrocyclic systems.