4-(formylmethylene)-2,6-diphenyl-4H-thiopyran | 75548-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫吡喃类
• 英文名称: 4-(formylmethylene)-2,6-diphenyl-4H-thiopyran
• 英文别名: 2-(2,6-Diphenylthiopyran-4-ylidene)acetaldehyde
• CAS: 75548-93-5
• 化学式: C₁₉H₁₄OS
• 分子量: 290.386
• InChiKey: DOHZZUGVGKYRRN-UHFFFAOYSA-N

物化性质

• 沸点：
  486.1±45.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(formylmethylene)-2,6-diphenyl-4H-thiopyran 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  New donors with two-electron oxidation. Synthesis and electrochemical properties of highly conjugated bis(4H-thiopyrans) and bis(flavenes)

  摘要：

  DOI：

  10.1021/jo00164a024

文献信息

• Proaromatic pyranylidene chalcogen analogues and cyclopenta[ c ]thiophen-4,6-dione as electron donors and acceptor in efficient charge-transfer chromophores
  作者：Parmeshwar Solanke、Sylvain Achelle、Nolwenn Cabon、Oldřich Pytela、Alberto Barsella、Bertrand Caro、Françoise Robin-le Guen、Jan Podlesný、Milan Klikar、Filip Bureš

  DOI：10.1016/j.dyepig.2016.07.008

  日期：2016.11

  Fifteen new push-pull chromophores based on a proaromatic pyranylidene donor and its chalcogen analogues and various electron acceptor moieties were synthesized in a straightforward manner. These model molecules were designed and prepared to investigate the concept of proaromaticity as a tool to tune the fundamental properties of push-pull systems. All target chromophores with systematically varied

  以一种直接的方式合成了15个新的推拉发色团，这些团基于原芳香族吡喃亚基供体及其硫属类似物和各种电子受体部分。设计并准备了这些模型分子，以研究亲芳香性的概念，以此作为调节推挽系统基本特性的工具。通过电化学，吸收光谱和EFISH实验结合DFT计算，进一步研究了结构变化的所有目标发色团。利用硫族/受体取代，π系统的延伸以及沿吡喃环的取代位置等结构变化，HOMO-LUMO间隙可在2.18至1.41 eV的范围内调整。一个新的强大的吸电子部分c ]噻吩-4，6-二酮（ThDione）也已经开发出来。
• Extreme red shifted SERS nanotags
  作者：Matthew A. Bedics、Hayleigh Kearns、Jordan M. Cox、Sam Mabbott、Fatima Ali、Neil C. Shand、Karen Faulds、Jason B. Benedict、Duncan Graham、Michael R. Detty

  DOI：10.1039/c4sc03917c

  日期：——

  Extreme red-shifted nanotags have been developed and they provide effective SERS with picomolar detection limits when excited at 1280 nm.

  极端红移的纳米标记已经开发出来，当在1280纳米激发时，它们提供有效的表面增强拉曼散射（SERS），可以检测到皮克摩尔级别。
• Synthesis and reactions of 2,6-diphenyl-4-(trimethylsilyl)-4H-thiopyran
  作者：Chin H. Chen、Jeffrey J. Doney、George A. Reynolds

  DOI：10.1021/jo00343a015

  日期：1982.2
• γ-Methylene chalcogenapyrans and benzopyrans as proaromatic donors in “push–pull” Fischer type carbene complexes: Influences of chalcogen atom and chain length on the electronic and N.L.O. properties of these molecules
  作者：N. Faux、B. Caro、F. Robin-Le Guen、P. Le Poul、K. Nakatani、E. Ishow

  DOI：10.1016/j.jorganchem.2005.07.049

  日期：2005.11

  A new class of push-pull molecules bearing gamma-methylene chalcogenapyran and benzopyran nucleus as proaromatic donors and methoxypentacarbonyltungstene carbene fragment as acceptors is described. N.L.O. properties (as mu beta by EFISH) of these complexes have been investigated. The influence of the unsaturated chain length, of the presence of the fused aromatic ring and of the chalcogen atom on the first hyperpolarizability values are shown. (c) 2005 Elsevier B.V. All rights reserved.
• Synthesis and NLO Properties of 4‐(4 <i>H</i> ‐Chalcogenopyran‐4‐ylidene and 4 <i>H</i> ‐chalcogenochromen‐4‐ylidene)‐1‐(phenylthio)but‐2‐enylidene Complexes – Electronic Influence of the Carbene Fragment
  作者：Nadège Faux、Françoise Robin‐Le Guen、Pascal Le Poul、Bertrand Caro、Keitaro Nakatani、Eléna Ishow、Stéphane Golhen

  DOI：10.1002/ejic.200600300

  日期：2006.9

  AbstractThe synthesis of 4‐(4H‐chalcogenopyran‐4‐ylidene and 4H‐chalcogenochromen‐4‐ylidene)‐1‐(phenylthio)but‐2‐enylidene complexes is described and their non‐linear optical (NLO) properties have been investigated (as μβ by EFISH). NMR studies and X‐ray crystallographic analyses show that the (phenylthio)carbene fragment has a better electron‐withdrawing capability than the methoxy analogues and, likewise, the corresponding thiocarbenes have a more significant pyrylium character. The μβ values of these complexes were obtained from EFISH experiments. The microscopic NLO response is sensitive to the nature of the intracyclic chalcogen atom, the nature of the metal centre and the benzo‐annulation of the heterocycle. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)