4-[2-[3-[2-(4-methoxyphenyl)ethynyl]phenyl]ethynyl]benzonitrile | 1151549-82-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-[2-[3-[2-(4-methoxyphenyl)ethynyl]phenyl]ethynyl]benzonitrile
• CAS: 1151549-82-4
• 化学式: C₂₄H₁₅NO
• 分子量: 333.389
• InChiKey: YWBNMASQRXRCDX-UHFFFAOYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  548.4±45.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Trimethylsilyl-diphenyl-phosphinoacetylen 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium tert-butylate 、 四丁基氟化铵 、 双氧水 、 二异丙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 43.0h， 生成 4-[2-[3-[2-(4-methoxyphenyl)ethynyl]phenyl]ethynyl]benzonitrile
  参考文献：
  名称：

  用于保护末端乙炔的Ph2P（O）基团

  摘要：

  新开发了末端乙炔保护基Ph 2 P（O）。该保护基可以通过CuI催化的磷酸化并随后用H 2 O 2氧化而容易地引入末端乙炔。在Sonogashira偶联中，Ph 2 P（O）保护的乙炔保持完好无损，并且它们的高极性使得可以轻松将所需的偶联产物与副产物分离。通过用t -BuOK处理，Ph 2 P（O）保护的乙炔转化为相应的末端乙炔。 炔烃-磷酸化-保护基-偶联

  DOI：

  10.1055/s-0030-1261223

文献信息

• One-Pot Transformation of Me₃Si-/Ph₂P(O)-Protected Ethynes to Unsymmetrical Arylethynes
  作者：Li-fen Peng、Jia-ying Lei、Li Wu、Zi-long Tang、Zhi-peng Luo、Yin-chun Jiao、Xin-hua Xu

  DOI：10.3184/174751918x15269925671284

  日期：2018.6

  Me₃Si-/Ph₂P(O)-protected ethynes were successfully transformed to unsymmetrical arylethynes via a one-pot Ph₂P(O)-deprotection/ [Pd(dppf)Cl₂]-catalysed coupling and one-pot Me₃Si-deprotection/Sonogashira coupling under mild conditions and in high yield. Unsymmetrical phenylethynes, unsymmetrical extended phenylene ethynylenes and unsymmetrical anthrylethynes were successfully synthesised in good to excellent yields.

  在温和的条件下，通过一锅 Ph2P(O)-脱保护/[Pd(dppf)Cl2]-催化偶联和一锅 Me3Si-Deprotection/Sonogashira 偶联，成功地将 Me3Si-/Ph2P(O)-protected ethynes 转化为非对称的芳炔类化合物，而且收率很高。成功合成了非对称苯乙炔、非对称扩展苯乙炔和非对称蒽乙炔，产率从良好到极佳。
• Emission from Regioisomeric Bis(phenylethynyl)benzenes during Pulse Radiolysis
  作者：Shingo Samori、Sachiko Tojo、Mamoru Fujitsuka、Torben Ryhding、Aaron G. Fix、Brittany M. Armstrong、Michael M. Haley、Tetsuro Majima

  DOI：10.1021/jo900494j

  日期：2009.5.15

  Emission from charge recombination between radical cations and anions of a series of regioisomeric 1,4-, 1,3-, and 1,2-bis(phenylethynyl)benzenes (bPEBs) substituted by various electron donor and/or acceptor groups was measured during pulse radiolysis in benzene (Bz). The formation of bPEB in the excited singlet state ((1)bPEB*) can be attributed to the charge recombination between bPEB(center dot+) and bPEB(center dot-), which are initially generated from the radiolytic reaction. This mechanism is reasonably explained by the relationship between the annihilation enthalpy change (-Delta H degrees) for the charge recombination of bPEB(center dot+) and bPEB(center dot-) and excitation energy of (1)bPEB*. Since the degree of the pi-conjugation in the S-1 state and HOMO-LUMO levels of bPEB change with the substitution pattern of phenylacetylene groups on the central benzene ring and the various kinds of donor and/or acceptor group, the fine-tuning of the emission color and intensity of bPEB can be easily carried out during pulse radiolysis in Bz. For donor-acceptor-substituted bPEB, it was found that the difference in the charge transfer conjugated pathways between donor and acceptor substituents (linear-, cross-, and "bent"-conjugated pathways) strongly influenced the HOMO-LUMO energy gap.
• Ph2P(O) Group for Protection of Terminal Acetylenes
  作者：Akihiro Orita、Junzo Otera、Xin Yang、Daisuke Matsuo、Yoshinori Suzuma、Jing-Kun Fang、Feng Xu、Shingo Kajiyama、Nagatoshi Koumura、Kohjiro Hara

  DOI：10.1055/s-0030-1261223

  日期：2011.10

  A protecting group Ph2P(O) for terminal ethyne was newly developed. This protecting group can be introduced readily to terminal ethyne by CuI-catalyzed phosphination and subsequent oxidation with H2O2. Ph2P(O)-protected ethynes remained intact in Sonogashira coupling, and their high polarity enabled easy separation of the desired coupling product from by-products. By treatment with t-BuOK, Ph2P(O)-protected

  新开发了末端乙炔保护基Ph 2 P（O）。该保护基可以通过CuI催化的磷酸化并随后用H 2 O 2氧化而容易地引入末端乙炔。在Sonogashira偶联中，Ph 2 P（O）保护的乙炔保持完好无损，并且它们的高极性使得可以轻松将所需的偶联产物与副产物分离。通过用t -BuOK处理，Ph 2 P（O）保护的乙炔转化为相应的末端乙炔。 炔烃-磷酸化-保护基-偶联