(Z/E)-tetrahydrothiophen-3-one tosylhydrazone | 1708-23-2

• 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: (Z/E)-tetrahydrothiophen-3-one tosylhydrazone
• 英文别名: N'-(dihydrothiophen-3(2H)-ylidene)-4-methylbenzenesulfonohydrazide；4-methyl-N-(thiolan-3-ylideneamino)benzenesulfonamide
• CAS: 1708-23-2
• 化学式: C₁₁H₁₄N₂O₂S₂
• 分子量: 270.376
• InChiKey: WYVLXGQPOHHEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z/E)-tetrahydrothiophen-3-one tosylhydrazone 在 氯化亚砜 作用下， 生成 4,6-dihydro-<3,4-d>-thieno-1,2,3-thiadiazole 、 4,5-dihydro-<2,3-d>-thieno-1,2,3-thiadiazole
  参考文献：
  名称：

  双（硫代二亚甲基）-四硫富瓦烯（BTDM-TTF）。具有相关氧化性能的新型π电子供体

  摘要：

  报道了新的硫代烷基取代的四硫富瓦烯双（硫代二亚甲基）四硫富瓦烯的合成和一些物理性质。BTDM-TTF的氧化电位表明分子内库仑排斥能低。

  DOI：

  10.1016/s0040-4039(01)93950-4
• 作为产物：
  描述：

  四氢噻吩-3-酮 、 对甲苯磺酰肼 以 甲醇 为溶剂， 反应 0.5h， 生成 (Z/E)-tetrahydrothiophen-3-one tosylhydrazone
  参考文献：
  名称：

  Metal-Free Coupling of Saturated Heterocyclic Sulfonylhydrazones with Boronic Acids

  摘要：

  The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp(2)-sp(3) linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.

  DOI：

  10.1021/jo402526z

文献信息

• Synthesis of spirocyclic dihydropyrazoles from tosylhydrazones and electron-deficient alkenes
  作者：Timothy L. Wootton、Daniel M. Allwood

  DOI：10.1039/d2ob00093h

  日期：——

  three–dimensionality. Herein, we demonstrate a procedurally simple method for the preparation of a range of spirocyclic dihydropyrazoles. The protocol utilises bench stable cyclic tosylhydrazones, which are trivial to prepare from the parent cyclic ketone without need for purification, and commercially available electron deficient alkenes. The synthetic utility of the core scaffold is also demonstrated

  螺环代表了一类多样化的分子，由于其广泛的生物活性和固有的分子三维度，它们在制药工业中受到了极大的关注。在此，我们展示了一种程序简单的方法，用于制备一系列螺环二氢吡唑。该协议使用台式稳定的环状甲苯磺酰腙，无需纯化即可从母体环状酮中制备，以及市售的缺电子烯烃。核心支架的合成效用也被证明突出了在药物化学和药物开发计划中的应用潜力。
• 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.
• Metal-Free Coupling of Saturated Heterocyclic Sulfonylhydrazones with Boronic Acids
  作者：Daniel M. Allwood、David C. Blakemore、Alan D. Brown、Steven V. Ley

  DOI：10.1021/jo402526z

  日期：2014.1.3

  The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp(2)-sp(3) linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
• Bis(thiodimethylene)-tetrahiafulvalene (BTDM-TTF). A new π-electron donor with relevant oxidation properties
  作者：C. Rovira、N. Santalō、J. Veciana

  DOI：10.1016/s0040-4039(01)93950-4

  日期：1989.1

  The synthesis and some physical properties of a new thioalkyl substituted tetrathiafulvalene, bis(thiodimethylene)tetrathiafulvalene, are reported. Oxidation potentials of BTDM-TTF indicate a low intramolecular Coulomb repulsion energy.

  报道了新的硫代烷基取代的四硫富瓦烯双（硫代二亚甲基）四硫富瓦烯的合成和一些物理性质。BTDM-TTF的氧化电位表明分子内库仑排斥能低。