2-(methylthio)-4,5-dimethyl-1,3-dithiolium iodide | 105580-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(methylthio)-4,5-dimethyl-1,3-dithiolium iodide
• 英文别名: 4,5-dimethyl-2-methylthio-1,3-dithiolium iodide；4,5-Dimethyl-2-methylthio-1,3-dithioliumiodid；4,5-Dimethyl-2-methylsulfanyl-1,3-dithiol-1-ium;iodide
• CAS: 105580-73-2
• 化学式: C₆H₉S₃*I
• 分子量: 304.24
• InChiKey: AABXRRGYKMEFPI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  蒽酮 、 2-(methylthio)-4,5-dimethyl-1,3-dithiolium iodide 以 吡啶 、 溶剂黄146 为溶剂， 以88%的产率得到10-(4,5-Dimethyl-1,3-dithiol-2-ylidene)anthracene-9(10H)-one
  参考文献：
  名称：

  Moore, Adrian J.; Bryce, Martin R., Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 157 - 168

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-dimethyl-[1,3]dithiole-2-thione 、 碘甲烷 以 乙腈 为溶剂， 生成 2-(methylthio)-4,5-dimethyl-1,3-dithiolium iodide
  参考文献：
  名称：

  π-扩展的四硫富瓦烯衍生物中的分子内电荷转移相互作用

  摘要：

  提出了新的电子给体（D）-电子受体（A）TTF结构，其中两个电子给体1,3,2-二硫醇部分通过π桥连接到弱电子接受性喹喔啉部分（D-π-A化合物9a和9b以及两个1,3-二硫基-2-亚烷基部分通过π桥连接至电子接受的噻吩并[3,4-b]喹喔啉桥（D-π-A-π-D化合物12a − c）在理论计算中预测并通过紫外可见光谱和循环伏安法测定证实存在键间分子内电荷转移（ICT）相互作用，这项工作构成了喹喔啉作为D中电子接受部分的首次应用。 -π-A化合物。

  DOI：

  10.1021/jo0489317

文献信息

• Redox-active, functionalised [3]- and [4]-dendralenes
  作者：Malcolm A. Coffin、Martin R. Bryce、Andrei S. Batsanov、Judith A. K. Howard

  DOI：10.1039/c39930000552

  日期：——

  A series of [3]- and [4]-dendralenes, functionalised with 1,3-dithiole groups, are synthesised and shown by cyclic voltammetry to undergo reversible multi-stage redox reactions to yield tri- and tetra-cation species, respectively; the X-ray crystal structure of a [3]-dendralene derivative is reported.

  合成了一系列具有 1,3 二硫代官能团的 [3]- 和 [4]- 树枝烯，并通过循环伏安法显示其发生了可逆的多级氧化还原反应，分别生成了三阳离子和四阳离子物种；报告了一种 [3]- 树枝烯衍生物的 X 射线晶体结构。
• Bryce, Martin R.; Davison, Gordon R.; Batsanov, Andrei S., Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2295 - 2302
  作者：Bryce, Martin R.、Davison, Gordon R.、Batsanov, Andrei S.、Howard, Judith A. K.

  DOI：——

  日期：——
• Bis- and tris(tetrathiafulvalenes) (TTFs) derived from reactions of the TTF-thiolate anion
  作者：Martin R. Bryce、Gary J. Marshallsay、Adrian J. Moore

  DOI：10.1021/jo00044a020

  日期：1992.8

  A range of new bis- and tris-TTF derivatives has been prepared using the TTF-thiolate anion 2 as a key intermediate. Thiolate anion 2 reacts with 2-bromoethanol to yield alcohol 3 from which the bis- and tris-TTF systems 4-7 have been obtained by reaction with the appropriate acid chloride. Subsequent reactions of the malonate anion of dimeric TTF 7 yield derivatives 8-10, which include the amphiphilic system 8. Thiolate anion 2 reacts with bis- and tris(bromomethyl)benzene to yield bis- and tris-TTF derivatives 11 and 12, respectively. Thioester 13, which serves as a shelf-stable precursor of thiolate anion 2, has been used in the synthesis of bis-TTF systems 17 and 18. The solution electrochemistry of the new multi-TTF derivatives has been studied by cyclic voltammetry, which reveals that the TTF moieties do not interact to any significant extent.
• Donor–π-Acceptor Species Derived from Functionalised 1,3-Dithiol-2-ylidene Anthracene Donor Units Exhibiting Photoinduced Electron Transfer Properties: Spectroscopic, Electrochemical, X-Ray Crystallographic and Theoretical Studies
  作者：Andrei S. Batsanov、Martin R. Bryce、Malcolm A. Coffin、Andrew Green、Ronald E. Hester、Judith A. K. Howard、Igor K. Lednev、Nazario Martín、Adrian J. Moore、John N. Moore、Enrique Ortí、Luis Sánchez、María Savirón、Pedro M. Viruela、Rafael Viruela、Tian-Qing Ye

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2580::aid-chem2580>3.3.co;2-#

  日期：1998.12.4

  Novel single-component donor- acceptor species 7 and 8 have been synthesised from substituted 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)one 6 by reaction with Lehnert's reagent and with N,N'-bis(trimethylsilyl)carbodiimide, respectively. The steady-state UV/visible spectra of these systems contain a solvatochromic band arising from intramolecular charge transfer between the donor and acceptor groups Ultrafast time-resolved spectroscopy shows that the excited state formed on photolysis has a lifetime of 170-400 ps, which depends strongly on solvent polarity. Cyclic voltammetric data indicate the presence of two active redox centres in the molecules: electrochemical oxidation and reduction form cation radicals and anion radicals, respectively. The X-ray crystal structures of compounds 6a, 7b and 11a reveal that all three molecules are severely distorted from planarity, with the central ring of the anthracenediylidene moiety adopting a boat conformation. The molecular structures of 6, 7 and 11 have been investigated theoretically at the ab initio 6-31G* level. Calculated geometries are in good agreement with the X-ray data and clearly show the decrease in steric hindrance along the series 11>7>8>6. The calculations support the intramolecular charge-transfer nature of the lowest energy absorption band observed for 6, 7 and 8, and explain the origin of the redox properties for these compounds. The optimised geometries of the cation radical, anion radical and dianion of compound 7 illustrate the structural changes induced by the charging process. For the dianion, the steric interactions are alleviated by rotation of the acceptor dicyanomethylene unit, but the presence of the donor dithiole group hinders the achievement of a fully aromatic planar structure for the central anthracene skeleton.
• 1,3-Dithiol-2-ylidene derivatives of 1,3-indanedione
  作者：Martin R. Bryce、Malcolm A. Coffin、Adrian J. Moore、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/s0040-4020(99)00530-x

  日期：1999.8

  The synthesis is described of a series of mono-, bis-, and tris(1,3-dithiol-2-ylidene) derivatives 7, 9 and 10 starting from 1,3-indanedione. Cyclic voltammetric data establish that the pi-electron donor ability of these molecules increases in the sequence 7 < 9 < 10, which is consistent with stabilisation of the cationic species by the presence of additional 1,3-dithiole units. The X-ray crystal structure of a complex (7a)(2). TCNQ is reported. Short intramolecular S ... O contacts are observed within moiety 7a. The mean planes of 7a and TCNQ are almost parallel forming planar layers within which ribbons of TCNQ molecules are intercalated by double ribbons of molecule 7a all stretched along the x direction. (C) 1999 Elsevier Science Ltd. All rights reserved.