4-Brombenzoesaeure-n-octadecylester | 70153-15-0

• 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-Brombenzoesaeure-n-octadecylester
• 英文别名: octadecyl 4-bromo-benzoate；cctadecyl 4-bromobenzoate；octadecyl 4-bromobenzoate；Octadecyl-p-brombenzoat
• CAS: 70153-15-0
• 化学式: C₂₅H₄₁BrO₂
• 分子量: 453.503
• InChiKey: VYRFSDPAFGIQSW-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  503.8±23.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Brombenzoesaeure-n-octadecylester 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 4-Ethinyl-benzoesaeure-n-octadecylester
  参考文献：
  名称：

  Pyrido[1,2-a]pyrazine - Startprodukte für regioselektive Ringtransformationen und supramolekulare Architekturen / Pyrido[1,2-a]pyrazines - 用于区域选择性环转化反应和超分子结构的起始材料

  摘要：

  易于获得的 1 型吡啶并 [1,2-a] 吡嗪是环转化反应的通用构件。 使用杂环醌（如喹啉-2,5,8-三酮 4a-c），一种高度区域选择性的 [4+2 ]-环加成反应发生在第一步，然后是环转化级联反应。1,6-二氮杂蒽-2,9,10-三酮 5a-e 具有额外的联吡啶亚结构，可以作为主要产物分离.为了对类型1的起始产物进行改性，进行了与炔属苯甲酸酯9a，b的金属催化交叉偶联反应。以良好收率获得的改性吡啶并吡嗪10a，b可以通过类比转化为1a,b 成环稠合杂环醌 12a,b。

  DOI：

  10.1515/znb-2002-0413
• 作为产物：
  描述：

  硬脂醇 、 4-溴苯甲酸乙酯 在 iron(III)-acetylacetonate 、 sodium carbonate 作用下， 以 正己烷 为溶剂， 反应 7.0h， 以98%的产率得到4-Brombenzoesaeure-n-octadecylester
  参考文献：
  名称：

  Transesterification catalyzed by iron(III) β-diketonate species

  摘要：

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.009

文献信息

• Surface-Induced Selection During In Situ Photoswitching at the Solid/Liquid Interface
  作者：Sara Bonacchi、Mohamed El Garah、Artur Ciesielski、Martin Herder、Simone Conti、Marco Cecchini、Stefan Hecht、Paolo Samorì

  DOI：10.1002/anie.201412215

  日期：2015.4.13

  Here we report for the first time a submolecularly resolved scanning tunneling microscopy (STM) study at the solid/liquid interface of the in situ reversible interconversion between two isomers of a diarylethene photoswitch, that is, open and closed form, self‐assembled on a graphite surface. Prolonged irradiation with UV light led to the in situ irreversible formation of another isomer as by‐product

  在这里，我们首次报道了在二芳基乙烯光开关的两个异构体之间原位可逆相互转化的固体/液体界面的亚分子分辨扫描隧道显微镜（STM）研究，即开放和封闭形式，它们自组装在石墨表面。长时间用紫外线照射会导致原位不可逆地形成另一种异构体，作为反应的副产物，这是由于其优先的物理吸附作用在表面积累的缘故。通过使用简单而强大的热力学模型，我们为观察到的表面诱导的一种异构形式的选择提供了定量描述。
• Nucleophilic Acyl Substitutions of Esters with Protic Nucleophiles Mediated by Amphoteric, Oxotitanium, and Vanadyl Species
  作者：Chien-Tien Chen、Jen-Huang Kuo、Cheng-Hsiu Ku、Shiue-Shien Weng、Cheng-Yuan Liu

  DOI：10.1021/jo0484878

  日期：2005.2.1

  [GRAPHICS]A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO(acac)(2)) and vanadyl chloride (VOCl2-(THF)(x)) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid- or base-sensitive) 1degrees and 2degrees alcohols can be carried out chemoselectively in refluxed toluene or xylene in a 1:1 substrate stoichiometry using 1 mol % catalyst loading. The resultant products were furnished in 85-100% yields by simple aqueous workup to remove water-soluble catalysts. The new NAS protocol is also amenable to amines and thiols in 74-91% yields, albeit with higher loading (2.5 equiv) of protic nucleophiles. Representative examples of commercial interests such as Padimate 0 and antioxidant additives for plastics were also examined to demonstrate their practical applications. A 1:1 adduct between TiO(acac)2 and a given 1-octadecanol was identified as (C18H37O)(2)Ti(acac)(2) and was responsible for its subsequent NAS of methyl esters.
• Transesterification catalyzed by iron(III) β-diketonate species
  作者：Shiue-Shien Weng、Chih-Shueh Ke、Fong-Kuang Chen、You-Fu Lyu、Guan-Ying Lin

  DOI：10.1016/j.tet.2011.01.009

  日期：2011.3

  A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)(3) or other iron(III) beta-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric mu-alkoxy-bridged iron (III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron beta-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric mu-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)(2)(O-n-Bu)](2) derived from the alcoholysis of Fe(dbm)(3) under alkaline conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• Pyrido[1,2-a]pyrazine - Startprodukte für regioselektive Ringtransformationen und supramolekulare Architekturen / Pyrido[1,2-a]pyrazines - Starting Materials for Regioselective Ringtransformation Reactions and Supramolecular Architectures
  作者：D. Müller、B. Frank、R. Beckert、H. Görls

  DOI：10.1515/znb-2002-0413

  日期：2002.4.1

  The easily available pyrido[1,2-a]pyrazines of type 1 are versatile building blocks for ring transformation reactions.W ith heterocyclic quinones such as quinoline-2,5,8-triones 4a-c, a highly regioselective [4+2]-cycloaddition reaction takes place in the first step, followed by a ring transformation cascade.T he 1,6-diazaanthracene-2,9,10-triones 5a-e, which possess an additional bipyridine substructure

  易于获得的 1 型吡啶并 [1,2-a] 吡嗪是环转化反应的通用构件。 使用杂环醌（如喹啉-2,5,8-三酮 4a-c），一种高度区域选择性的 [4+2 ]-环加成反应发生在第一步，然后是环转化级联反应。1,6-二氮杂蒽-2,9,10-三酮 5a-e 具有额外的联吡啶亚结构，可以作为主要产物分离.为了对类型1的起始产物进行改性，进行了与炔属苯甲酸酯9a，b的金属催化交叉偶联反应。以良好收率获得的改性吡啶并吡嗪10a，b可以通过类比转化为1a,b 成环稠合杂环醌 12a,b。