3-(5,5-dimehtyl-[1,3]dioxan-2-yl)thiophene-2,5-dicarbaldehyde | 883556-04-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-(5,5-dimehtyl-[1,3]dioxan-2-yl)thiophene-2,5-dicarbaldehyde
• 英文别名: 3-(5,5-Dimethyl-1,3-dioxan-2-yl)thiophene-2,5-dicarbaldehyde；3-(5,5-dimethyl-1,3-dioxan-2-yl)thiophene-2,5-dicarbaldehyde
• CAS: 883556-04-5
• 化学式: C₁₂H₁₄O₄S
• 分子量: 254.307
• InChiKey: OHTNEAPSRDBOTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5,5-dimehtyl-[1,3]dioxan-2-yl)thiophene-2,5-dicarbaldehyde 在 哌啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (E,E)-2,5-bis(2-thien-2-ylvinyl)-3-(1,3-indandion-2-ylmethylen)thiophene
  参考文献：
  名称：

  Synthesis and characterization of novel styryl-substituted oligothienylenevinylenes

  摘要：

  A number of 3-monosubstituted bis(thienylvinyl)thiophenes, suitable for the preparation of electronically-variable poly(thienytenevinylene)s have been synthesized for the first time. These materials have been characterized by both NMR spectroscopy and mass spectrometry, and a single crystal X-ray structure analysis of (E,E)-3-(5,5-dimethyl[1,3]dioxin-2-yl)-2,5-bis(2-thien-2-ylvinyl)thiophene has shown that the planarity of the terthienylenevinylene chain is maintained on substitution at the 3 position of the central thiophene ring. UV/visible spectroscopy measurements are reported and cyclic voltammetric measurements show that, with the exception of (E,E,E)-2,5-bis(2-thien-2-ylvinyl)-3-(2-(4-dimethylaminophenyl)vinyl)-thiophene, electroactive films are produced on electrochemical oxidation of the monomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.017
• 作为产物：
  描述：

  2,2-二甲基-1,3-丙二醇 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.5h， 生成 3-(5,5-dimehtyl-[1,3]dioxan-2-yl)thiophene-2,5-dicarbaldehyde
  参考文献：
  名称：

  Synthesis and characterization of novel styryl-substituted oligothienylenevinylenes

  摘要：

  A number of 3-monosubstituted bis(thienylvinyl)thiophenes, suitable for the preparation of electronically-variable poly(thienytenevinylene)s have been synthesized for the first time. These materials have been characterized by both NMR spectroscopy and mass spectrometry, and a single crystal X-ray structure analysis of (E,E)-3-(5,5-dimethyl[1,3]dioxin-2-yl)-2,5-bis(2-thien-2-ylvinyl)thiophene has shown that the planarity of the terthienylenevinylene chain is maintained on substitution at the 3 position of the central thiophene ring. UV/visible spectroscopy measurements are reported and cyclic voltammetric measurements show that, with the exception of (E,E,E)-2,5-bis(2-thien-2-ylvinyl)-3-(2-(4-dimethylaminophenyl)vinyl)-thiophene, electroactive films are produced on electrochemical oxidation of the monomers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.017

文献信息

• Synthesis and characterization of novel styryl-substituted oligothienylenevinylenes
  作者：Pawel Wagner、Amy M. Ballantyne、Kenneth W. Jolley、David L. Officer

  DOI：10.1016/j.tet.2005.12.017

  日期：2006.3

  A number of 3-monosubstituted bis(thienylvinyl)thiophenes, suitable for the preparation of electronically-variable poly(thienytenevinylene)s have been synthesized for the first time. These materials have been characterized by both NMR spectroscopy and mass spectrometry, and a single crystal X-ray structure analysis of (E,E)-3-(5,5-dimethyl[1,3]dioxin-2-yl)-2,5-bis(2-thien-2-ylvinyl)thiophene has shown that the planarity of the terthienylenevinylene chain is maintained on substitution at the 3 position of the central thiophene ring. UV/visible spectroscopy measurements are reported and cyclic voltammetric measurements show that, with the exception of (E,E,E)-2,5-bis(2-thien-2-ylvinyl)-3-(2-(4-dimethylaminophenyl)vinyl)-thiophene, electroactive films are produced on electrochemical oxidation of the monomers. (c) 2005 Elsevier Ltd. All rights reserved.