4-thiocyanobenzaldehyde | 89898-72-6

• 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: 4-thiocyanobenzaldehyde
• 英文别名: 4-formylphenyl thiocyanate；4-thiocyanatobenzaldehyde；4-Rhodan-benzaldehyd；(4-formylphenyl) thiocyanate
• CAS: 89898-72-6
• 化学式: C₈H₅NOS
• 分子量: 163.2
• InChiKey: FZGVVJAMZPDGOX-UHFFFAOYSA-N

物化性质

• 熔点：
  78 °C
• 沸点：
  310.9±25.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-thiocyanobenzaldehyde 在 sodium sulfide 、 溶剂黄146 、 硫酸肼 作用下， 生成 bis-(4-methylsulfanyl-benzylidene)-hydrazine
  参考文献：
  名称：

  Friedlaender; Lenk, Chemische Berichte, 1912, vol. 45, p. 2087

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium thioacyanate 、 4-碘苯甲醛 在 copper(I) thiocyanate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以20%的产率得到4-thiocyanobenzaldehyde
  参考文献：
  名称：

  Thiol-Derivatized Porphyrins for Attachment to Electroactive Surfaces

  摘要：

  The attachment of porphyrin monomers and multiporphyrin arrays in controlled architectures on electroactive surfaces opens many opportunities for electrochemical studies. Toward this goal, we have developed routes for the preparation of thiol-derivatized porphyrin monomers and porphyrin building blocks that require minimal or no handling of free thiols. Routes to S-protected p-thiobenzaldehydes and m-(thiomethyl)benzaldehydes have been developed. TRIO sets of mesosubstituted porphyrins with variation in electrochemical potentials have been prepared for vertical or horizontal orientation with respect to the electroactive surface. In one set, each porphyrin bears one S-protected p-thiophenyl unit and substituents at the three remaining meso-positions. In the other set each porphyrin possesses four S-protected m-(thiomethyl)phenyl units. Tuning the electrochemical potential in the former set has been achieved by variation of the meso substituents (mesityl, 2,4,6-trimethoxyphenyl, n-pentyl, pentafluorophenyl) and in the latter set by variation of the central metal (Zn, Cu, Co, Ag). Six thiol protecting groups ES-cyano, S-(N-ethylcarbamoyl), S-acetyl, S-(9-anthrylmethyl), S-(2,4-dinitrophenyl), S-pivaloyl] have been found to be compatible with porphyrin formation and metalation with zinc. The S-cyano, S-(N-ethylcarbamoyl), and S-acetyl groups undergo in situ cleavage and/or binding on a gold surface. Of these three, only the S-acetyl protecting group is compatible with the Pd-mediated iodo-ethyne coupling conditions for the preparation of multiporphyrin arrays. Three trans-substituted porphyrin building blocks have been prepared for the synthesis of multiporphyrin arrays that can be attached to an electroactive surface. One porphyrin has two mesityl, one p-iodophenyl, and one p-(S-acetylthio)phenyl substituent for vertical positioning, and two porphyrins each have two m-iodophenyl and two S-protected m-(thiomethyl)phenyl substituents for horizontal positioning. Altogether, 16 free base and 16 metalloporphyrins have been prepared. This work establishes the foundation for preparing diverse thiol-derivatized porphyrin monomers and building blocks.

  DOI：

  10.1021/jo9911084

文献信息

• Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates
  作者：Yang Chen、Hongyi Qi、Ning Chen、Demin Ren、Jiaxi Xu、Zhanhui Yang

  DOI：10.1021/acs.joc.9b00965

  日期：2019.7.19

  Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver

  硫醚通过氟引发的脱烷基氰化反应转化为硫氰酸酯。Selectfluor被用作氧化剂，三甲基甲硅烷基氰化物被用作氰化试剂。精简的过程是用户友好的，操作简单且经济的步骤。当前的机理研究表明，硫自由基阳离子和氰基自由基都涉及。它们结合在一起释放氰基ulf，这是脱烷基化后向硫氰酸酯的中间体。或者，亲核机理也是可能的。我们的脱脱烷基氰化在合成具有强亲电功能的硫氰酸酯方面也很有效。
• A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS
  作者：Nan Sun、Liusheng Che、Weimin Mo、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1039/c4ob02208d

  日期：——

  A facile and generalized synthesis of aryl thiocyanates has been established via the CuCl-catalyzed oxidative coupling of arylboronic acids with TMSNCS. The reaction could be conducted at RT and under an O₂ atmosphere.

  已建立一种简便且通用的合成芳基硫氰酸酯的方法，通过CuCl催化的芳基硼酸与TMSNCS的氧化偶联反应。该反应可在室温和氧气氛下进行。
• High density non-volatile memory device
  申请人：Bocian F. David

  公开号：US20050041494A1

  公开（公告）日：2005-02-24

  This invention provides novel high density memory devices that are electrically addressable permitting effective reading and writing, that provide a high memory density (e.g., 10 15 bits/cm 3 ), that provide a high degree of fault tolerance, and that are amenable to efficient chemical synthesis and chip fabrication. The devices are intrinsically latchable, defect tolerant, and support destructive or non-destructive read cycles. In a preferred embodiment, the device comprises a fixed electrode electrically coupled to a storage medium having a multiplicity of different and distinguishable oxidation states wherein data is stored in said oxidation states by the addition or withdrawal of one or more electrons from said storage medium via the electrically coupled electrode.

  本发明提供了一种新型的高密度存储器件，可进行电气寻址，实现有效的读写，提供高存储密度（例如，1015比特/厘米3），提供高度的容错性，并可进行高效的化学合成和芯片制造。这些设备本质上是可锁定的、缺陷容忍的，并支持破坏性或非破坏性读取周期。在优选实施例中，该设备包括一个固定电极与一个存储介质电性耦合，该存储介质具有多个不同和可区分的氧化态，通过向存储介质添加或提取一个或多个电子，将数据存储在所述氧化态中。
• High density memory device
  申请人：Bocian F. David

  公开号：US20060209587A1

  公开（公告）日：2006-09-21

  This invention provides novel high density memory devices that are electrically addressable permitting effective reading and writing, that provide a high memory density (e.g., 10 15 bits/cm 3 ), that provide a high degree of fault tolerance, and that are amenable to efficient chemical synthesis and chip fabrication. The devices are intrinsically latchable, defect tolerant, and support destructive or non-destructive read cycles. In a preferred embodiment, the device comprises a fixed electrode electrically coupled to a storage medium having a multiplicity of different and distinguishable oxidation states wherein data is stored in said oxidation states by the addition or withdrawal of one or more electrons from said storage medium via the electrically coupled electrode.

  本发明提供了一种新型的高密度存储器件，具有电学可寻址性，可有效地进行读写操作，提供高存储密度（例如，1015比特/立方厘米），具有高度的容错性，并且适用于高效的化学合成和芯片制造。这些器件本质上是可锁定的、缺陷容忍的，并支持破坏性或非破坏性读取周期。在首选实施例中，该器件包括一个固定电极，与一个具有多种不同和可区分氧化态的存储介质电学耦合，通过电学耦合的电极向存储介质中添加或撤回一个或多个电子，将数据存储在所述氧化态中。
• High density non-volatile memory device incorporating thiol-derivatized porphyrins
  申请人：The Regents of the University of California

  公开号：US06208553B1

  公开（公告）日：2001-03-27

  This invention provides novel high density memory devices that are electrically addressable permitting effective reading and writing, that provide a high memory density (e.g., 1015 bits/cm3), that provide a high degree of fault tolerance, and that are amenable to efficient chemical synthesis and chip fabrication. The devices are intrinsically latchable, defect tolerant, and support destructive or non-destructive read cycles. In a preferred embodiment, the device comprises a fixed electrode electrically coupled to a storage medium comprising one or more thiol-derivatized porphyrins. The storage medium has a multiplicity of different and distinguishable oxidation states and data is stored in said oxidation states by the addition or withdrawal of one or more electrons from the storage medium via the electrically coupled electrode(s).

  本发明提供了一种新型高密度存储器件，可进行有效的读写操作，提供高存储密度（例如，1015位/厘米3），具有高度的容错性，并且易于进行高效的化学合成和芯片制造。这些器件具有固有的锁存、容错和支持破坏性或非破坏性读取循环的特性。在一种优选实施方案中，该器件包括一个固定电极，与一个包含一种或多种硫醇衍生的卟啉的存储介质电性耦合。该存储介质具有多种不同和可区分的氧化状态，并且通过向存储介质中添加或撤回一个或多个电子来在这些氧化状态中存储数据，通过电性耦合的电极实现。