(((5-ethynyl-1,3-phenylene)bis(oxy))bis(methylene))dibenzene | 871592-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (((5-ethynyl-1,3-phenylene)bis(oxy))bis(methylene))dibenzene
• 英文别名: 1-ethynyl-3,5-bis(phenylmethoxy)benzene
• CAS: 871592-09-5
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: BILOTRDQYAYUQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (((5-ethynyl-1,3-phenylene)bis(oxy))bis(methylene))dibenzene 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 乙醚 、 丙酮 为溶剂， 以94%的产率得到1-(2-Bromoethynyl)-3,5-bis(phenylmethoxy)benzene
  参考文献：
  名称：

  End-Cap Stabilized Oligoynes: Model Compounds for the Linear sp Carbon Allotrope Carbyne

  摘要：

  Three series of differently 3,5-disubstituted alpha,omega-diphenylpolyynes Ar-(CdropC)(n)-Ar (n=2, 4, 6, 8, 10) were synthesized under optimized Cadiot-Chodkiewicz conditions, isolated and completely characterized. These compounds can be considered as model substances for the hypothetical one-dimensional carbon allotrope carbyne C, The longest sp-carbon chain contains 20 atoms and is therefore the longest, purely organic polyyne studied with NMR techniques. Extinction coefficients over 600000m(-1)cm(-1) represent the highest measured quantitative values for that compound class so far. Comparisons with previous investigations and electrochemical studies allow the assignment of absorption for both wavelength regions structuring the UV/Vis spectra. Based on the trends in the spectroscopic behaviour of those molecules with increasing chain length. electronic as well as the NMR properties of carbyne are predicted, in line with our previously reported results. The observed stability mise the. properties pro synthesis of even longer polyynes.

  DOI：

  10.1002/1521-3765(20020118)8:2<408::aid-chem408>3.0.co;2-l
• 作为产物：
  描述：

  3,5-二苄氧基苯甲醛 在 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 (((5-ethynyl-1,3-phenylene)bis(oxy))bis(methylene))dibenzene
  参考文献：
  名称：

  End-Cap Stabilized Oligoynes: Model Compounds for the Linear sp Carbon Allotrope Carbyne

  摘要：

  Three series of differently 3,5-disubstituted alpha,omega-diphenylpolyynes Ar-(CdropC)(n)-Ar (n=2, 4, 6, 8, 10) were synthesized under optimized Cadiot-Chodkiewicz conditions, isolated and completely characterized. These compounds can be considered as model substances for the hypothetical one-dimensional carbon allotrope carbyne C, The longest sp-carbon chain contains 20 atoms and is therefore the longest, purely organic polyyne studied with NMR techniques. Extinction coefficients over 600000m(-1)cm(-1) represent the highest measured quantitative values for that compound class so far. Comparisons with previous investigations and electrochemical studies allow the assignment of absorption for both wavelength regions structuring the UV/Vis spectra. Based on the trends in the spectroscopic behaviour of those molecules with increasing chain length. electronic as well as the NMR properties of carbyne are predicted, in line with our previously reported results. The observed stability mise the. properties pro synthesis of even longer polyynes.

  DOI：

  10.1002/1521-3765(20020118)8:2<408::aid-chem408>3.0.co;2-l

文献信息

• Regioselective Synthesis of Vinyl Halides, Vinyl Sulfones, and Alkynes: A Tandem Intermolecular Nucleophilic and Electrophilic Vinylation of Tosylhydrazones
  作者：Devi Prasan Ojha、Kandikere Ramaiah Prabhu

  DOI：10.1021/ol503114n

  日期：2015.1.2

  in tandem at the carbene center to install an electrophile and a nucleophile on the same carbon. This metal-free concept, which is unprecedented, has been illustrated by regioselective synthesis of a variety of vinyl halides, vinyl sulfones, and alkyne derivatives.

  重氮物质以分子间方式被两个独立的离子物质串联在卡宾中心，从而在同一碳上安装了亲电子试剂和亲核试剂。这种无金属的概念是前所未有的，已通过多种乙烯基卤化物，乙烯基砜和炔烃衍生物的区域选择性合成得到了说明。
• Deconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran
  作者：Ling Zhang、Tongxiang Cao、Huanfeng Jiang、Shifa Zhu

  DOI：10.1002/anie.201915212

  日期：2020.3.16

  An unprecedented deconstructive reorganization strategy for the de novo synthesis of hydroxylated benzofurans from kojic acid- or maltol-derived alkynes is reported. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six-carbon component. Through this

  报道了一种空前的解构重组策略，用于从曲酸或麦芽酚衍生的炔烃从头合成羟基化苯并呋喃。在该反应中，同时构造了苯环和呋喃环，而曲酸或麦芽酚的吡喃酮部分被解构，然后以六碳组分重组为苯环。通过这种策略，以取代模式可调节的方式将至少一个游离羟基引入苯环，而无需进行保护-脱保护和氧化还原调节。通过这种方法，已经有效地制备了具有不同取代模式的大量羟基化苯并呋喃衍生物。