1-iodo-4-(phenylbuta-1,3-diyn-1-yl) benzene | 1209009-05-1

• 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-iodo-4-(phenylbuta-1,3-diyn-1-yl) benzene
• 英文别名: 1-Iodo-4-(4-phenylbuta-1,3-diynyl)benzene
• CAS: 1209009-05-1
• 化学式: C₁₆H₉I
• 分子量: 328.152
• InChiKey: PHPLUEQQDAKSRV-UHFFFAOYSA-N

物化性质

• 沸点：
  395.0±34.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-iodo-4-(phenylbuta-1,3-diyn-1-yl) benzene 、 4-乙炔基苯甲醚 在 copper(l) iodide 、 四(三苯基膦)钯 、 二异丙胺 作用下， 以 甲苯 为溶剂， 以78%的产率得到1-methoxy-4-((4-(phenylbuta-1,3-diyn-1-yl)phenyl)ethynyl)benzene
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y
• 作为产物：
  描述：

  1-(4-iodophenyl)-5-phenylpenta-1,4-diyn-3-one 在 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯苯 作用下， 反应 24.5h， 以54%的产率得到1-iodo-4-(phenylbuta-1,3-diyn-1-yl) benzene
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y

文献信息

• Visible-light-activated copper(<scp>i</scp>) catalyzed oxidative C_sp–C_sp cross-coupling reaction: efficient synthesis of unsymmetrical conjugated diynes without ligands and base
  作者：Arunachalam Sagadevan、Ping-Chiang Lyu、Kuo Chu Hwang

  DOI：10.1039/c6gc01463a

  日期：——

  A novel visible-light-promoted copper-catalysed process for highly selective Csp-Csp cross-coupling reaction of terminal alkynes at room temperature is described. The current photochemical method is simple, high functional group compatible, and...

  描述了一种新型的可见光促进的铜催化的炔烃在室温下高度选择性的Csp-Csp交叉偶联反应的方法。当前的光化学方法简单，具有高官能团相容性，并且...
• 不对称1,4-二芳基丁二炔类化合物的合成方法
  申请人：南京理工大学

  公开号：CN106366065A

  公开（公告）日：2017-02-01

  本发明公开了一种不对称1,4‑二芳基丁二炔类化合物的合成方法，采用“双消除法”，以α‑亚甲基砜和炔醛为原料，合成得到了一系列不对称1,4‑二芳基丁二炔化合物。本发明不需要重金属参与，绿色环保；较之金属炔化物与卤代端炔的交叉偶联原料合成较为简单；较之端炔的自身偶联反应其可合成不对称共轭二炔。
• Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes
  作者：Jing-Kun Fang、De-Lie An、Kan Wakamatsu、Takeharu Ishikawa、Tetsuo Iwanaga、Shinji Toyota、Daisuke Matsuo、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tetlet.2009.12.023

  日期：2010.2

  A series of diphenylamino-substituted phenylene-(poly)ethynylenes were successfully synthesized by a combination of Sonogashira coupling and double elimination protocol of p-substituted sulfones. When UV-light was irradiated, the amino-substituted phenylene-(poly)ethynylene emitted strong luminescence. The emission underwent a large bathochromic shift in polar solvent because of stabilization of their charge-separated excited states. Analyses of fluorescence life times of aminoacetylenes revealed that radiationless process was suppressed in the polar solvent CH2Cl2, resulting in high quantum yields. (C) 2009 Elsevier Ltd. All rights reserved.