dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester | 138519-02-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester
• 英文别名: dimethyl (4,5-bis(methylthio)-1,3-dithiol-2-yl)phosphonate；2-Dimethoxyphosphoryl-4,5-bis(methylsulfanyl)-1,3-dithiole
• CAS: 138519-02-5
• 化学式: C₇H₁₃O₃PS₄
• 分子量: 304.416
• InChiKey: OVJSSRKHLBSWAW-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)
• 沸点：
  404.0±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 4,5-bis(methylthio)-1,3-dithiole phosphonate ester 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 生成 2-[9,10-Bis-(4,5-bis-methylsulfanyl-[1,3]dithiol-2-ylidene)-8-(2-hydroxy-ethoxy)-9,10-dihydro-anthracen-1-yloxy]-ethanol
  参考文献：
  名称：

  Novel 9,10-Bis(1,3-dithiol-2-ylidene)-9,10- dihydroanthracene Derivatives Bridged by a Crown Ether Unit at the 1,8-Positions: A New Type of Redox-switchable Hosts Undergoing Reversible Structural Changes

  摘要：

  Novel redox-switchable host molecules (2) composed of a 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene unit and a crown ether moiety bridging the 1,8-positions have been synthesized. Cyclic voltammetry and X-Ray analyses revealed that the molecules undergo a significant structural change upon oxidation. 'H-NMR titration experiments on the neutral and dication states show that the binding abilities of the dication states for alkali metal cations (Li+, Na+, K+) are considerably lower than those of the neutral molecules. The binding properties of 2 were also investigated by cyclic voltammetry.

  DOI：

  10.3987/com-05-s(t)55
• 作为产物：
  描述：

  三甲氧基磷 以100%的产率得到
  参考文献：
  名称：

  Fourmigue Marc, Krebs Frederik C., Larsen Jan, Synthesis, (1993) N 5, S 509-513

  摘要：

  DOI：

文献信息

• Oxidative intramolecular cyclization of 2,2′-bis(1,4-dithiafulven-6-yl)-3,3′-bithienyls affording novel bis(1,3-dithiole) electron donors
  作者：Akira Ohta、Yoshiro Yamashita

  DOI：10.1039/c39950001761

  日期：——

  The title bis(1,3-dithiole) compounds containing a 3,3′-bithienyl unit undergo an intramolecular coupling reaction at the 6-positions of the dithiafulvenyl groups by oxidation to give cyclization products in high yields.

  标题为含有3,3'-双噻吩单元的双(1,3-二噻吩)化合物通过氧化在二硫福烯基团的6位发生分子内耦合反应，从而高产率地生成环化产物。
• New strategies and building blocks for functionalised 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene derivatives, including pyrrolo-annelated derivatives and π-extended systems with intramolecular charge-transferThis paper is Molecular Saddles Part 10. For Part 9 see reference 5c.Electronic supplementary information (ESI) available: NOE spectra for compound 23. See http://www.rsc.org/suppdata/ob/b2/b211153p/
  作者：Christian A. Christensen、Martin R. Bryce、Andrei S. Batsanov、Jan Becher

  DOI：10.1039/b211153p

  日期：2003.1.30

  new functionalised 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene (TTFAQ) derivatives have been synthesised from the key di(halomethyl) building blocks, 10-[4,5-bis(bromomethyl)-1,3-dithiol-2-ylidene]-anthracene-9(10H)-one 10, 10-[4,5-bis(chloromethyl)-1,3-dithiol-2-ylidene]anthracene-9(10H)-one 11 and 9-[4,5-bis(chloromethyl)-1,3-dithiol-2-ylidene]-10-[4,5-bis(hexylsulfanyl)- 1,3-dithiol-2-ylidene]-9

  在维尔斯迈尔条件下，将32和33的吡咯环单甲酰化，得到35和36，与2、4、5、7-四硝基芴反应后，得到供体-π受体二单元基38和39。溶液中的循环伏安法（CV）对于所有TTFAQ衍生物，其显示TTFAQ核的典型准可逆两电子氧化波的电势随取代基的不同而略有不同。例如，Eox的值通过分别21和38的吸电子蒽醌和四硝基芴单元提高。共轭TTFAQ二聚体23的CV显示出两个二电子氧化波，分别对应于23（2+）和23（4+）的依次形成（δEox = 130 mV），提供了明显的分子内电子相互作用的证据，即指示23（2+）充当共轭供体-pi-受体二价体，从而提高了其合作伙伴TTFAQ单元的氧化潜力。对23的光谱电化学研究支持这一解释。在TTFAQ-π-四硝基芴二单元38和39的UV-Vis光谱中可见到最大538 nm处的强分子内电荷转移带。据报道，化合物30、33和34的X射线晶体结构。 TTFAQ部
• 2,2′-(Cyclopenten-3,5-diylidene)bis(1,3-dithiole)s: novel electron donors undergoing deprotonation by oxidation
  作者：Yoshiro Yamashita、Shoji Tanaka、Masaaki Tomura

  DOI：10.1039/c39930000652

  日期：——

  The title bis(l,3-dithiole) donors containing a dimethylenecyclopentene skeleton afford a novel type of deeply coloured cation by deprotonation from the dication states.

  标题为含有二亚甲基环戊烯骨架的bis(l,3-二硫杂烯)给体通过从二价阳离子状态去质子化生成了一种新型深色阳离子。
• Synthesis and Electronic Properties of a Conjugated TTFAQ Trimer and Donor-Acceptor Ensembles of TTFAQ and Anthraquinone
  作者：Yuming Zhao、Min Shao、Guang Chen

  DOI：10.1055/s-2008-1032040

  日期：2008.2

  We report the first synthesis of a conjugated TTFAQ trimer as well as two TTFAQ-anthraquinone based donor-acceptor ensembles using Sonogashira and Horner-Wadsworth-Emmons reactions. Electronic absorption and electrochemical redox properties of these compounds are described.

  我们报告了利用 Sonogashira 反应和 Horner-Wadsworth-Emmons 反应首次合成的共轭 TTFAQ 三聚体以及两种基于 TTFAQ-蒽醌的供体-受体组合物。介绍了这些化合物的电子吸收和电化学氧化还原特性。
• Chiroptical and Redox Properties of a Tetrathiafulvalene Analogue with an Inserted Spiro Framework
  作者：Masashi Hasegawa、Daisuke Kurebayashi、Hideyo Matsuzawa、Yasuhiro Mazaki

  DOI：10.1246/cl.180358

  日期：2018.8.5

  A chiral spiro compound (1a) having 1,3-dithiol units has been synthesized as a stereogenic tetrathiafulvalene analogue. Spiro 1a was resolved into two enantiomers by chiral HPLC, and they exhibited remarkable chiroptical properties featuring dehydroindene-dithiol chromophore in C2 symmetry. In addition, electrochemical properties were also investigated by using cyclic voltammetry and electronic spectra of cationic species.

  合成了一种具有1,3-二硫醇单元的手性螺旋化合物（1a），作为立体异构体四硫富瓦烯的类似物。螺旋化合物1a通过手性高效液相色谱法被分离为两个对映体，它们展现了显著的手性光学特性，特征为具有C2对称性的脱氢印烯-二硫醇色团。此外，还通过循环伏安法和阳离子物种的电子光谱研究了其电化学性质。