(E)-5,5',6,6'-tetrahydro-Δ^2,2'-bithieno<2,3-d>-1,3-dithiole | 67188-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: (E)-5,5',6,6'-tetrahydro-Δ^2,2'-bithieno<2,3-d>-1,3-dithiole
• 英文别名: 5,5',6,6'-tetrahydro-Δ^2,2'-bithieno<2,3-d>-1,3-dithiol；trans-Di(4,5-dihydrothieno)-<2,3-b;2',3'-h>-1,4,5,8-tetrathiafulvalen；trans-Di(4,5-dihydrothieno)-[2,3-b;2',3'-h]-1,4,5,8-tetrathiafulvalen；(2E)-2-(5,6-dihydrothieno[2,3-d][1,3]dithiol-2-ylidene)-5,6-dihydrothieno[2,3-d][1,3]dithiole
• CAS: 67188-96-9
• 化学式: C₁₀H₈S₆
• 分子量: 320.57
• InChiKey: MVHCVVYUMFYYME-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-5,5',6,6'-tetrahydro-Δ^2,2'-bithieno<2,3-d>-1,3-dithiole 生成 (E)-5,6,5',6'-Tetrahydro-[2,2']bi[thieno[2,3-d][1,3]dithiolylidene]; compound with 2-(4-dicyanomethylene-cyclohexa-2,5-dienylidene)-malononitrile
  参考文献：
  名称：

  Rovira Concepcio, Veciana Jaume, Santalo Nuria, Tarres Judit, Cirujeda Jo+, J. Org. Chem, 59 (1994) N 12, S 3307- 3313

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-Dihydrothieno[2,3-d]-1,3-dithiol-2-thion 在 三甲氧基磷 作用下， 反应 3.0h， 以23%的产率得到(E)-5,5',6,6'-tetrahydro-Δ^2,2'-bithieno<2,3-d>-1,3-dithiole
  参考文献：
  名称：

  Synthesis of Several Isomeric Tetrathiafulvalene .pi.-Electron Donors with Peripheral Sulfur Atoms. A Study of Their Radical Cations

  摘要：

  An efficient synthesis of one new (10) and three previously reported (9, 11, and 12) pi-electron donors, which have one sulfur atom in each of the outer five-membered rings attached to the TTF system, is presented. The radical cations derived from 9-11 have been studied by ESR spectroscopy and the spin density distribution of these radical cations, as well as those of other related radical cations, have been determined by MO calculations and correlated with the ESR spectral data. The single-crystal X-ray structures of pi-donors 9 and 12 are reported. The most remarkable fact of these structures is the transverse intermolecular contacts between interstacked molecules. The external sulfur atoms of 9 play a central role in its transverse structural pattern. Complexes of donors 9 and 10 with tetracyano-p-quinodimethane (TCNQ) and tetrafluorotetracyano-p-quinodimethane (TC-NQF(4)) have been obtained and characterized.

  DOI：

  10.1021/jo00091a017

文献信息

• Improved Synthesis of the π-Electron Donor Bis(ethylenethio)tetrathiafulvalene (BET-TTF)
  作者：Aarón Pérez-Benítez、Judit Tarrés、Elisabet Ribera、Jaume Veciana、Concepció Rovira

  DOI：10.1055/s-1999-3451

  日期：1999.4

  Following a three step route, 5,6-dihydrothieno[2,3-d]-1,3-dithiol-2-one (5) was synthesized in gram quantities starting from commercially available reagents. Coupling of 5 with trimethyl phosphite gave the π-donor bis(ethylenethio)tetrathiafulvalene 1 in 80% yield.

  通过三步路线，我们利用市售试剂合成了 5,6-二氢噻吩并[2,3-d]-1,3-二硫环戊-2-酮 (5)。将 5 与亚磷酸三甲酯偶联，可得到Ï-载体双（乙烯硫基）四硫富戊烯 1，收率为 80%。
• Rovira Concepcio, Veciana Jaume, Santalo Nuria, Tarres Judit, Cirujeda Jo+, J. Org. Chem, 59 (1994) N 12, S 3307- 3313
  作者：Rovira Concepcio, Veciana Jaume, Santalo Nuria, Tarres Judit, Cirujeda Jo+

  DOI：——

  日期：——
• Synthesis of Several Isomeric Tetrathiafulvalene .pi.-Electron Donors with Peripheral Sulfur Atoms. A Study of Their Radical Cations
  作者：Concepcio Rovira、Jaume Veciana、Nuria Santalo、Judit Tarres、Joan Cirujeda、Elies Molins、Jordi Llorca、Enrique Espinosa

  DOI：10.1021/jo00091a017

  日期：1994.6

  An efficient synthesis of one new (10) and three previously reported (9, 11, and 12) pi-electron donors, which have one sulfur atom in each of the outer five-membered rings attached to the TTF system, is presented. The radical cations derived from 9-11 have been studied by ESR spectroscopy and the spin density distribution of these radical cations, as well as those of other related radical cations, have been determined by MO calculations and correlated with the ESR spectral data. The single-crystal X-ray structures of pi-donors 9 and 12 are reported. The most remarkable fact of these structures is the transverse intermolecular contacts between interstacked molecules. The external sulfur atoms of 9 play a central role in its transverse structural pattern. Complexes of donors 9 and 10 with tetracyano-p-quinodimethane (TCNQ) and tetrafluorotetracyano-p-quinodimethane (TC-NQF(4)) have been obtained and characterized.