2-(Triphenyl-λ⁵-phosphanylidene)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester | 88430-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(Triphenyl-λ⁵-phosphanylidene)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 2-(triphenyl-lambda5-phosphanylidene)-1,3-dithiole-4,5-dicarboxylate；dimethyl 2-(triphenyl-λ5-phosphanylidene)-1,3-dithiole-4,5-dicarboxylate
• CAS: 88430-82-4
• 化学式: C₂₅H₂₁O₄PS₂
• 分子量: 480.545
• InChiKey: YOQAUGHEXYRVIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(Triphenyl-λ⁵-phosphanylidene)-[1,3]dithiole-4,5-dicarboxylic acid dimethyl ester 生成 dimethyl 2-[8-[4,5-bis(methoxycarbonyl)-1,3-dithiol-2-ylidene]-7-bicyclo[4.2.0]octa-1,3,5-trienylidene]-1,3-dithiole-4,5-dicarboxylate
  参考文献：
  名称：

  LAKSHMIKANTHAM, M. V.;CAVA, M. P.;CARROLL, P. J., J. ORG. CHEM., 1984, 49, N 4, 726-728

  摘要：

  DOI：

文献信息

• Cycloaddition of acetylenedicarbaldehyde monoacetal and 2,4,5-trithioxo-1,3-dithiole: Ready access to novel highly extended and sulfur-rich analogues of tetrathiafulvalene (TTF)
  作者：Philippe Leriche、Alain Gorgues、Michel Jubault、Jan Becher、Jesús Orduna、Javier Garin

  DOI：10.1016/0040-4039(95)00014-4

  日期：1995.2

  Thiones 2(′), 4(′) and 3(′) are readily prepared from title compounds. Bis-olefinations of 3 with Akiba's reagents W or H afford 8 which can cyclize into 9 upon acid areatment. (i-PrO)3P mediated coupling of 4 with 5′ affords 7 whose formolysis in 10 and bis-olefination with W or H yields target compound 1. The π-donor ability and stability of 8 and 1 are discussed.

  由标题化合物易于制备亚硫醚2（'），4（'）和3（'）。的双烯化反应3与秋叶的试剂W¯¯或ħ得到8，其可环化到9在酸areatment。（我-Pro）3 P间接的耦合4与5'得到7，其在formolysis 10和双烯与W¯¯或ħ得到目标化合物1。8和1的π供体能力和稳定性 讨论。
• Low Oxidation Potential Tetrathiafulvalene Analogues Based on 3,4-Dialkoxythiophene π-Conjugating Spacers
  作者：Said Akoudad、Pierre Frère、Nicolas Mercier、Jean Roncali

  DOI：10.1021/jo981312b

  日期：1999.6.1

  Tetrathiafulvalene analogues involving dihexyloxythiophene (1), ethylenedioxythiophene (2), and bis(3,4-dihexyloxy-2-thienyl)ethylene (3) as conjugating spacer and diversely substituted at the 1,3-dithiole ring (R) have been synthesized. Electronic absorption spectra show the expected decrease of HOMO-LUMO gap when increasing the electron-releasing power of R or the length of the conjugating spacer. Cyclic voltammetry (CV) shows that whereas compounds 1 and 2 are reversibly oxidized into their cation radical and dication through two one-electron steps, for compounds 3 the dication is formed directly via a two-electron transfer. Comparison of the data for compounds 2 and 3 with those of their respective analogues based on thiophene and dithienylethylene shows that introduction of the electron-donating alkoxy groups at the 3 and 4 positions of the thiophene ring produces a 150-200 mV negative shift of the first redox potential (E degrees(1)). On the other hand, CV data for compounds 1 and 2 reveal several unusual features such as E degrees(1) approximate to 0.10 V/SCE ranking among-the lowest known to date and a Coulombic repulsion between positive charges in the dication larger than for the analogue ct-donors based on unsubstituted thiophene. These results are interpreted by a major reorganization of the electronic distribution in the donor molecule due to alkoxy groups: the highest electron density moving from the 1,3-dithiole moiety toward the central thiophene ring.
• 2-butyne-1,4-diylidene-2,2′bis (1,3-dithiole): acetylenic analogs of tetrathiafulvalene
  作者：Abdallah Khanous、Alain Gorgues、Fernand Texier

  DOI：10.1016/s0040-4039(00)88551-2

  日期：1990.1
• Synthesis of the First 1,3-Ditellurole-Containing Radialene-Type TTF Derivatives
  作者：Desikan Rajagopal、M. V. Lakshmikantham、Michael P. Cava

  DOI：10.1021/ol026227b

  日期：2002.7.1

  [GRAPHICS]The first synthesis of dendralene-type TTF derivatives bearing a 1,3-ditellurole ring has been achieved. Preliminary electrochemical results are presented.