18-phenoxy-1-octadecene | 813460-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 18-phenoxy-1-octadecene
• 英文别名: [(Octadec-17-en-1-yl)oxy]benzene；octadec-17-enoxybenzene
• CAS: 813460-71-8
• 化学式: C₂₄H₄₀O
• 分子量: 344.581
• InChiKey: WEQRTSIIRDGIFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  18-phenoxy-1-octadecene 在 9-borabicyclo[3.3.1]nonane dimer 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 168.67h， 生成 S-(18-phenoxyoctadecyl) 1-thioacetate
  参考文献：
  名称：

  Preparation of High Quality Electrical Insulator Self-Assembled Monolayers on Gold. Experimental Investigation of the Conduction Mechanism through Organic Thin Films

  摘要：

  Self-assembled monolayers (SAMS) form highly ordered, stable dielectrics on conductive surfaces. Being able to attach larger-area contacts in a MIM (metal-insulator-metal) diode, their electrical properties can be determined. In this paper, the electrical conduction through thiolate SAMS of different alkyl chain lengths formed on gold surfaces were studied and discussed. The influence of the headgroup with respect to the surface quality and prevention of short circuits is investigated. Phenoxy terminated alkanethiols were found to form high quality SAMS with perfect insulating properties. Synthesis of the required terminally substituted long chain thiols have been developed. The I(V) characteristics of MIM structures formed with these SAMS are measured and simulated according to theoretical tunneling models for electrical conductivity through thin organic layers. SAM based electronic devices will become especially important for future nanoscale applications, where they can serve as insulators, gate dielectric of FETs, resistors, and capacitor structures.

  DOI：

  10.1021/ja0548992
• 作为产物：
  描述：

  potassium phenolate 、 18-溴-1-十八烯 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以92%的产率得到18-phenoxy-1-octadecene
  参考文献：
  名称：

  Preparation of High Quality Electrical Insulator Self-Assembled Monolayers on Gold. Experimental Investigation of the Conduction Mechanism through Organic Thin Films

  摘要：

  Self-assembled monolayers (SAMS) form highly ordered, stable dielectrics on conductive surfaces. Being able to attach larger-area contacts in a MIM (metal-insulator-metal) diode, their electrical properties can be determined. In this paper, the electrical conduction through thiolate SAMS of different alkyl chain lengths formed on gold surfaces were studied and discussed. The influence of the headgroup with respect to the surface quality and prevention of short circuits is investigated. Phenoxy terminated alkanethiols were found to form high quality SAMS with perfect insulating properties. Synthesis of the required terminally substituted long chain thiols have been developed. The I(V) characteristics of MIM structures formed with these SAMS are measured and simulated according to theoretical tunneling models for electrical conductivity through thin organic layers. SAM based electronic devices will become especially important for future nanoscale applications, where they can serve as insulators, gate dielectric of FETs, resistors, and capacitor structures.

  DOI：

  10.1021/ja0548992

文献信息

• Method for Synthesizing Long-Chain Phosphonic Acid Derivatives and Thiol Derivatives
  申请人：Effenberger Franz

  公开号：US20080275273A1

  公开（公告）日：2008-11-06

  A process for synthesizing long-chain phosphonic acid derivatives and thiol derivative is disclosed. One embodiment provides organic compounds which can form a self-assembled monolayer and are obtained by reaction of an olefin with a thiocarboxylic acid and subsequent hydrogenation to give the thiol, or with a phosphite and subsequent hydrolysis to give the phosphonic acid.

  本发明揭示了一种合成长链膦酸衍生物和硫醇衍生物的过程。其中一种实施方式提供了有机化合物，它们可以形成自组装单层，并通过烯烃与硫代羧酸的反应和随后的氢化反应得到硫醇，或者通过膦酸酯和随后的水解反应得到膦酸。
• Synthesis method for a compound used to form a self-assembled monolayer, compound for forming a self-assembled monolayer, and layer structure for a semiconductor component
  申请人：Effenberger Franz

  公开号：US20060160272A1

  公开（公告）日：2006-07-20

  A synthesis method of a compound used to form a self-assembled monolayer used in a semiconductor component is provided. A method includes a first step of replacing a terminal halogen of an ω-haloalk-1-ene with a compound having at least one aromatic group, and a second step of hydrosilylating the reaction product of the first step. Reaction products of the first step include octadec-17-enyloxybenzene, 4-octadec-17″-enyloxy-1,1′-biphenyl, 2-heptadec-16′-enylthiophene, and 2-octadec-17′-enylthiophene. Monolayers provided include 18-phenoxyoctadecyl)trichlorosilane, [18-(1′,1″-biphenyl-4′-yloxy)octadecyl]trichlorosilane, (17-thien-2′-ylheptadecyl)trichlorosilane, (18-thien-2′-yloctadecyl)trichlorosilane, and 4-(18′-trichlorosilyloctadecyloxy)benzonitrile. An organic field effect transistor having monolayers according to embodiments of the invention is provided.

  本发明提供了一种用于形成半导体元件中使用的自组装单分子层的化合物的合成方法。该方法包括第一步，用至少含有一个芳香基团的化合物替换ω-卤代烯烃的末端卤素，以及第二步，对第一步反应产物进行氢硅化反应。第一步的反应产物包括十八烷基-17-烯氧基苯、4-十八烷基-17″-烯氧基-1,1′-联苯、2-十七烷基-16′-烯基噻吩和2-十八烷基-17′-烯基噻吩。所提供的单分子层包括18-苯氧基十八烷基三氯硅烷、[18-(1′,1″-联苯-4′-氧基)十八烷基]三氯硅烷、(17-噻吩-2′-基十七烷基)三氯硅烷、(18-噻吩-2′-基十八烷基)三氯硅烷和4-(18′-三氯硅基十八烷氧基)苯腈。本发明实施例提供了具有单分子层的有机场效应晶体管。
• Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2
  作者：Rebecca A. Splain、Laura L. Kiessling

  DOI：10.1016/j.bmc.2010.04.068

  日期：2010.6.1

  Despite the prevalence and importance of carbohydrate polymers, the molecular details of their biosynthesis remain elusive. Many enzymes responsible for the synthesis of carbohydrate polymers require a 'primer' or 'initiator' carbohydrate sequence. One example of such an enzyme is the mycobacterial galactofuranosyltransferase GlfT2 (Rv3808c), which generates an essential cell wall building block. We recently demonstrated that recombinant GlfT2 is capable of producing a polymer composed of alternating beta-(1,5) and beta-(1,6)-linked galactofuranose (Galf) residues. Intriguingly, the length of the polymers produced from a synthetic glycosyl acceptor is consistent with those found in the cell wall. To probe the mechanism by which polymer length is controlled, a collection of initiator substrates has been assembled. The central feature of the synthetic route is a ruthenium-catalyzed cross-metathesis as the penultimate transformation. Access to synthetic substrates has led us to postulate a new mechanism for length control in this template-independent polymerization. Moreover, our investigations indicate that lipids possessing but a single galactofuranose residue can act as substrates for GlfT2. (C) 2010 Elsevier Ltd. All rights reserved.
• SYNTHESEVERFAHREN FÜR EINE VERBINDUNG ZUR BILDUNG EINER SELBSTORGANISIERENDEN MONOLAGE, VERBINDUNG ZUR BILDUNG EINER SELBSTORGANISIERENDEN MONOLAGE UND EINE SCHICHTSTRUKTUR FÜR EIN HALBLEITERBAUELEMENT
  申请人：Qimonda AG

  公开号：EP1636294B1

  公开（公告）日：2007-03-28
• METHODE ZUR SYNTHESE VON LANGKETTIGEN PHOSPHONS[UREDERIVATEN UND THIOLDERIVATEN
  申请人：Qimonda AG

  公开号：EP1817804A2

  公开（公告）日：2007-08-15