2-(formylmethylene)-4,5-dimethyl-1,3-dithiole | 87815-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 2-(formylmethylene)-4,5-dimethyl-1,3-dithiole
• 英文别名: 2-(4,5-Dimethyl-1,3-dithiol-2-ylidene)acetaldehyde
• CAS: 87815-66-5
• 化学式: C₇H₈OS₂
• 分子量: 172.272
• InChiKey: GFBOVRRMVHSQGF-UHFFFAOYSA-N

物化性质

• 熔点：
  51-52 °C
• 沸点：
  250.3±40.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-二乙基-2-硫代巴比妥酸 、 2-(formylmethylene)-4,5-dimethyl-1,3-dithiole 以 乙醇 为溶剂， 反应 4.42h， 以52%的产率得到1,3-diethyl-5-[2-(4,5-dimethyl-[1,3]-dithiol-2-ylidene)-ethylidene]-2-thiobarbituric acid
  参考文献：
  名称：

  Novel NLO-phores with Proaromatic Donor and Acceptor Groups

  摘要：

  Novel D-pi-A NLO-phores based on the 1,3-dithiol-2-ylidene donor and the thiobarbituric acceptor moieties have been prepared. Modification of the length and rigidity of the pi-spacer allows the first systematic study of the second-order nonlinear optical properties of doubly proaromatic merocyanines. The pi-electron donor efficiency of the 1,3-dithiol-2-ylidene group is superior to that of the tetrathiafulvalenyl group.

  DOI：

  10.1021/ol0352005
• 作为产物：
  描述：

  [Tributyl-(4,5-dimethyl-1,3-dithiol-2-yl)-lambda5-phosphanyl] perchlorate 、 草酸醛 以83%的产率得到
  参考文献：
  名称：

  YOSHIDA, ZEN-ICHI;KAWASE, TOKUZO;AWAJI, HIROSHI;SUGIMOTO, IWAO;SUGIMOTO, +, TETRAHEDRON LETT., 1983, 24, N 33, 3469-3472

  摘要：

  DOI：

文献信息

• Aromatic/Proaromatic Donors in 2-Dicyanomethylenethiazole Merocyanines: From Neutral to Strongly Zwitterionic Nonlinear Optical Chromophores
  作者：Raquel Andreu、Elena Galán、Jesús Orduna、Belén Villacampa、Raquel Alicante、Juan T. López Navarrete、Juan Casado、Javier Garín

  DOI：10.1002/chem.201002158

  日期：2011.1.17

  whereas 4H‐pyran‐4‐ylidene‐ and 4‐pyridylidene‐containing compounds are zwitterionic and 1,3‐dithiol‐2‐ylidene derivatives are close to the cyanine limit, anilino‐derived merocyanines are essentially neutral. This very large range of intramolecular charge transfer (ICT) gives rise to efficient second‐order NLO chromophores with μβ values ranging from strongly negative to strongly positive. In particular

  制备了推挽式化合物，其中一个芳香族电子供体与一个2-二氰基亚甲基噻唑受体结合。与具有芳香族供体的模型化合物相比，它们的性能更佳。结合实验（X射线衍射，1 H NMR，IR，拉曼，UV / Vis，非线性光学（NLO）测量）和理论研究表明，结构和溶剂效应决定了这些花菁的基态极化：而4 H含吡喃-4-亚烷基和4-吡啶亚基的化合物为两性离子型，1,3-二硫醇-2-亚烷基衍生物接近花青的限度，苯胺衍生的花菁本质上是中性的。分子内电荷转移（ICT）的范围非常广，可产生高效的二阶NLO生色团μβ值的范围从强负到强正。尤其是，吡喃亚烷基衍生物不寻常，因为它们在加长π间隔物时显示出ICT程度的提高，而该特征在于它们显示出的非常大的负μβ值。将形式为喹啉的2-二氰基亚甲基噻唑部分与原芳香族供体连接起来似乎是优化两性离子NLO发色团的一种有前途的方法。
• Synthesis, Structure, and Optical Properties of 1,4-Dithiafulvene-Based Nonlinear Optic-phores
  作者：Silvia Alías、Raquel Andreu、María Jesús Blesa、Santiago Franco、Javier Garín、Aurora Gragera、Jesús Orduna、Pilar Romero、Belén Villacampa、Magali Allain

  DOI：10.1021/jo070694v

  日期：2007.8.1

  conformational features, ground state polarization, and linear and nonlinear optical properties have been determined experimentally and theoretically, and the results are compared to those of tetrathiafulvalene-related derivatives. The newly prepared compounds show close to optimal bond length alternation values for maximizing the first molecular hyperpolarizability, and one of them displays the highest

  合成了具有芳香性1,4-二硫富烯电子供体和很少探索的1,1,3-三氰基-2-苯基丙烯受体的多烯非线性光学（NLO）-团。通过实验和理论确定了它们的构型和构象特征，基态极化以及线性和非线性光学性质，并将结果与​​四硫富瓦烯相关衍生物进行了比较。新制备的化合物表现出接近最优键长交替的值最大化所述第一分子超极化，并且它们中的一个显示最高μβ 0曾报道为基于dithiafulvene-NLO-phore值。还报道了二硫代富烯基亚甲基转移反应的第一个实例。
• Functionalized polyolefinic nonlinear optic chromophores incorporating the 1,3-dithiol-2-ylidene moiety as the electron-donating part
  作者：T. T. Nguyen、M. Sallé、J. Delaunay、A. Riou、P. Richomme、J. M. Raimundo、A. Gorgues、I. Ledoux、C. Dhenaut、J. Zyss、J. Orduna、J. Garín

  DOI：10.1039/a709055b

  日期：——

  The synthesis of a series of push-pull systems [donor (D)–acceptor (A)], associating the 1,3-dithiol-2-ylidene moiety (D) to various (A) fragments through polyolefinic linkages of various lengths, is described. Design optimization of these NLO phores isvia systematic determination of the molecular first hyperpolarizabilities beta; by the EFISH method. Selected compounds of this series, displaying the highest beta; values, are then chemically functionalized in order to promote their covalent grafting to polymeric backbones.

  本文介绍了一系列推拉系统[供体（D）-受体（A）]的合成过程，这些系统通过不同长度的聚烯烃连接将 1,3-二硫醇-2-亚基分子（D）与各种（A）片段连接起来。这些 NLO 磷光体的设计优化是通过 EFISH 方法系统地确定分子第一超极化率 beta。然后对该系列中显示出最高 beta 值的部分化合物进行化学官能化处理，以促进它们与聚合物骨架的共价接枝。
• Syntheses, structure and properties of vinylogous EDO-TTFs
  作者：T. Shirahata、T. Morikawa、H. Miyamoto、Y. Nakano、H. Yamochi、Y. Misaki

  DOI：10.1016/j.physb.2009.12.024

  日期：2010.6

  the dication state. X-ray crystal structure analysis of BMCEDO-EBDT reveals that the inter-molecular C-H···O type hydrogen bond is constructed between the hydrogen atom and the oxygen atom of the ethylenedioxy group. Single crystalline TCNQ complexes of DMEDO-EBDT and BTMEDO-EBDT have been prepared and their conducting properties and crystal structure have been investigated. The TCNQ complexes of DMEDO-EBDT

  我们合成了插烯 4,5-ethylenedioxy-tetrathiafulvalenes (EDO-TTFs), 4,5-ethylenedioxy-2,2'-ethanediylidenebis(1,3-dithiole) (EDO-EBDT), 4,5-dimethyl-4', 5'-ethylenedioxy-2,2'-ethanediylidene-bis(1,3-dithiole) (DMEDO-EBDT), 4,5-bis(thiomethyl)-4',5'-ethylenedioxy-2,2'-ethanediylidenebis ( 1,3-dithiole) (BTMEDO-EBDT) 和 4,5-bis(methoxycarbonyl)-4',5'-ethylenedioxy-2,2'-ethanediylide-nebis(1,3-dithiole) (BMCEDO-EBDT)
• Synthesis and Properties of Novel [5]Radialenes Substituted with Multiple 1,3-Dithiol-2-yildenes
  作者：Masafumi Ueda、Yui Ogura、Yohji Misaki

  DOI：10.1246/cl.130140

  日期：2013.5.5

  Novel [5]radialenes with four 1,3-dithiol-2-ylidene (DT) units (2) and ethylene analogs of [5]dendralene derivatives with five DT units (3) were synthesized. Cyclic voltammetry revealed that 2 exhi...

  合成了具有四个 1,3-二硫醇-2-亚基 (DT) 单元 (2) 的新型 [5] radialene 和具有五个 DT 单元 (3) 的 [5] 枝烯衍生物的乙烯类似物。循环伏安法显示，2...