Ethyl-thiocarbamic acid S-(4-formyl-phenyl) ester | 251989-52-3

• 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: Ethyl-thiocarbamic acid S-(4-formyl-phenyl) ester
• 英文别名: 4-[s-(n-Ethylcarbamoyl)thio]-benzaldehyde；S-(4-formylphenyl) N-ethylcarbamothioate
• CAS: 251989-52-3
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: RHMVTJDRMGRHTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡咯 、 五氟苯甲醛 、 Ethyl-thiocarbamic acid S-(4-formyl-phenyl) ester 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以10%的产率得到5,10,15-tris(2,3,4,5,6-pentafluorophenyl)-20-[4-[S-(N-ethylcarbamoyl)thio]phenyl]porphyrin
  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
• 作为产物：
  描述：

  5,5-dimethyl-2-(4-methylsulfanylphenyl)-1,3-dioxane 在 2,6-二甲基吡啶 、 苯基硫三甲基硅烷 、 间氯过氧苯甲酸 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.5h， 生成 Ethyl-thiocarbamic acid S-(4-formyl-phenyl) ester
  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

• 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
  申请人：The Regents of the University of California

  公开号：EP1210714A2

  公开（公告）日：2002-06-05
• EP1210714A4
  申请人：——

  公开号：EP1210714A4

  公开（公告）日：2006-01-04
• US7042755B1
  申请人：——

  公开号：US7042755B1

  公开（公告）日：2006-05-09
• US7518905B2
  申请人：——

  公开号：US7518905B2

  公开（公告）日：2009-04-14