1-[(4-Methylphenoxy)methyl]-2-nitrobenzene | 1378303-12-8

• 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: 1-[(4-Methylphenoxy)methyl]-2-nitrobenzene
• CAS: 1378303-12-8
• 化学式: C₁₄H₁₃NO₃
• mdl: MFCD20538236
• 分子量: 243.262
• InChiKey: OKCOOBVSCAMTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4-Methylphenoxy)methyl]-2-nitrobenzene 在 tetrafluoroboric acid 、 tin (IV) chloride pentahydrate 、 palladium diacetate 、 potassium carbonate 、 sodium nitrite 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 2-methyl-6H-benzo[c]chromene
  参考文献：
  名称：

  Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates

  摘要：

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.038
• 作为产物：
  描述：

  对甲酚 、 2-硝基苄溴 在 silica 、 四丁基溴化铵 、 月桂基三甲基溴化铵 作用下， 以 水 为溶剂， 反应 5.0h， 生成 1-[(4-Methylphenoxy)methyl]-2-nitrobenzene
  参考文献：
  名称：

  Williamson反应的静态相转移催化：Pickering界面催化†

  摘要：

  Pickering界面催化（PIC）系统被认为是设计高效静态双相催化反应的创新平台。在这项研究中，构建了具有高催化活性的静态PIC系统，用于Williamson反应的相转移催化系统。用阳离子表面活性剂DTAB（十二烷基三甲基溴化铵）改性的二氧化硅颗粒用作Pickering乳化剂，并构建稳定的Pickering乳液。乳液的液滴尺寸为21μm，并且在将乳液静置24小时后未观察到尺寸和分布的变化。由于DTA +在二氧化硅颗粒和酚酸根阴离子之间的竞争性吸附，因此第二层DTA +吸附在改性颗粒上的离子与酚酸根阴离子成对，离子对也可以进入第一层。这些改性的二氧化硅颗粒排列在水相和油相的界面，吸附的DTA +可以转移酚盐阴离子以催化PTC反应。可以将四丁基溴化铵（TBAB）用作助催化剂来增强催化反应。在PIC系统中，苄基溴衍生物的转化率达到90％以上，证明了其在工业合成中的潜在应用。

  DOI：

  10.1039/c9cy00620f

文献信息

• Chemoselective hydrogenation of nitrobenzyl ethers to aminobenzyl ethers catalyzed by palladium–nickel bimetallic nanoparticles
  作者：Wenwen Chen、Hailin Bao、Dingsheng Wang、Xinyan Wang、Yadong Li、Yuefei Hu

  DOI：10.1016/j.tet.2015.10.037

  日期：2015.12

  A highly efficient and chemoselective hydrogenation of nitrobenzyl ethers to aminobenzyl ethers was developed by using a novel palladium nickel bimetallic nanocatalyst. Since the catalytic selectivity was resulted from the synergistic effects between two metals rather than the traditional catalyst poisons, the hydrogenation proceeded smoothly under additive-free conditions. Thus, the work-up procedure was as simple as to recover the catalyst by a magnetic separation and then to evaporate the solvent. (C) 2015 Elsevier Ltd. All rights reserved.
• Photoactivatable Caged Compounds with AIE Characteristics: Method of Preparation and Applications
  申请人：TANG Benzhong

  公开号：US20150376112A1

  公开（公告）日：2015-12-31

  A photoactivatable caged compound (TPE-C) with AIE characteristics is designed and synthesized. TPE-C is non-emissive either in solution or in aggregated state, but its luminescence can be induced to emit strong cyan emission in aggregated state by UV irradiation. Such property enables TPE-C to be applied in photo-patterning and anti-counterfeiting related areas.
• US9919995B2
  申请人：——

  公开号：US9919995B2

  公开（公告）日：2018-03-20
• Synthesis of substituted 6H-benzo[c]chromenes: a palladium promoted ring closure of diazonium tetrafluoroborates
  作者：Jing Zhou、Liang-Zhu Huang、You-Qiang Li、Zhen-Ting Du

  DOI：10.1016/j.tetlet.2012.10.038

  日期：2012.12

  A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium salts tetrafluoroborate of benzyloxyphenyl (Method A), or phenoxymethyl phenyl (Method B). The transformation allows the synthesis of 6H-benzo[c]chromenes with a wide variety of functional groups and substitution patterns from simple and easily accessible precursors. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.
• Static phase transfer catalysis for Williamson reactions: Pickering interfacial catalysis
  作者：Qianqiang Zhao、Xiao Zhao、Hui Peng、Yang Liu、Lihui Yang、Jie Sun、Lei Yang、Yifeng Shen

  DOI：10.1039/c9cy00620f

  日期：——

  ion-pairs can also enter the first layer. These modified silica particles are arranged at the interface of the aqueous phase and the oil phase, and the adsorbed DTA+ can transfer phenolate anion to catalyze the PTC reaction. Tetrabutylammonium bromide (TBAB) can be used as a cocatalyst to enhance the catalytic reaction. The conversion rate of benzyl bromide derivatives reached more than 90% within the

  Pickering界面催化（PIC）系统被认为是设计高效静态双相催化反应的创新平台。在这项研究中，构建了具有高催化活性的静态PIC系统，用于Williamson反应的相转移催化系统。用阳离子表面活性剂DTAB（十二烷基三甲基溴化铵）改性的二氧化硅颗粒用作Pickering乳化剂，并构建稳定的Pickering乳液。乳液的液滴尺寸为21μm，并且在将乳液静置24小时后未观察到尺寸和分布的变化。由于DTA +在二氧化硅颗粒和酚酸根阴离子之间的竞争性吸附，因此第二层DTA +吸附在改性颗粒上的离子与酚酸根阴离子成对，离子对也可以进入第一层。这些改性的二氧化硅颗粒排列在水相和油相的界面，吸附的DTA +可以转移酚盐阴离子以催化PTC反应。可以将四丁基溴化铵（TBAB）用作助催化剂来增强催化反应。在PIC系统中，苄基溴衍生物的转化率达到90％以上，证明了其在工业合成中的潜在应用。