1,3-di-(1-propynyl)benzene

• 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: 1,3-di-(1-propynyl)benzene
• 英文别名: 1,3-di(prop-1-yn-1-yl)benzene；1,3-Bis(prop-1-ynyl)benzene
• 化学式: C₁₂H₁₀
• 分子量: 154.211
• InChiKey: ZOIGWUYXGMMUIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,2-di(prop-1-ynyl)benzene 、 1,3-di-(1-propynyl)benzene 在 (Me3CO)3W<*>CCMe3 作用下， 以 甲苯 为溶剂， 以19%的产率得到Pentacyclo[25.3.1.112,16.04,9.019,24]dotriaconta-1(31),4,6,8,12(32),13,15,19,21,23,27,29-dodecaen-2,10,17,25-tetrayne
  参考文献：
  名称：

  Miljanić, Ognjen Š.; Vollhardt, K. Peter C.; Whitener, Glenn D., Synlett, 2003, # 1, p. 29 - 34

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-Di-prop-2-ynyl-benzene 在 potassium tert-butylate 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-di-(1-propynyl)benzene
  参考文献：
  名称：

  Syntheses and Properties of Medium-Sized Metacyclophanediynes

  摘要：

  The syntheses of [11]metacyclophane-2,9-diyne (3), [4.4]metacyclophane-2,12-diyne (4), [4.4]orthometacyclophane-2,12-diyne (5), (Z)-[10]metacyclophane-5-ene-2,8-diyne (6), [10]metacyclophane-2,8-diyne (7), and 5-isopropylidene[9]metacyclophane-2,7-diyne (8) have been achieved. The systems could be stabilized by protecting the triple bonds in 3-8 with the Co-2(CO)(6) moiety. PE spectroscopic investigations of 3 and 6-8 gave no clear-cut evidence for homoconjugative interactions among the pi fragments. The triple bonds in 3-8 could be transformed into the corresponding cis double bands by applying 2-5 molar equiv of Schwartz's reagent (28). Treatment of 3, 4, and ? with t-BuOK allows the transformation of the propargylic moieties into allenic moieties, whereas the same treatment of 5 and 6 transforms the 2-butynyl bridges into 1,3-butadiene bridges, giving rise to several isomers. The structural assignments of 3-8 and their reaction products are based an their spectroscopic properties.

  DOI：

  10.1021/jo970327r

文献信息

• Direct Synthesis of 1-Arylprop-1-ynes with Calcium Carbide as an Acetylene Source
  作者：Lei Gao、Zheng Li

  DOI：10.1055/s-0037-1610718

  日期：2019.8

  A simple method is described for the synthesis of 1-arylprop-1-ynes directly from aromatic aldehyde p-tosylhydrazones by using calcium carbide as an acetylene source. The salient features of this protocol are its use of a readily available and easily handled source of acetylene, its operational simplicity, its high yield, and its broad substrate scope.

  描述了一种使用碳化钙作为乙炔源直接从芳香醛对甲苯磺酰腙合成 1-芳基丙-1-炔的简单方法。该协议的显着特点是使用容易获得且易于处理的乙炔来源、操作简单、产量高和底物范围广泛。
• A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes
  作者：Ding-Wei Ji、Yan-Cheng Hu、Hao Zheng、Chao-Yang Zhao、Qing-An Chen、Vy M. Dong

  DOI：10.1039/c9sc01527b

  日期：——

  Through rational evaluation of ligands and promoters, the reactivity of a key Pd(ii) species towards transmetalation or β-H elimination is manipulated.

  通过对配体和促进剂的理性评估，可以操控关键的Pd（II）物种对于金属转移或β-H消除的活性。
• Synthesis of diarylenynes by olefination of 1-arylpropyne with arylaldehyde and their optical properties
  作者：Kenta Shinohara、Takanori Nishida、Ryosuke Wada、Lifen Peng、Yuju Minoda、Akihiro Orita、Junzo Otera

  DOI：10.1016/j.tet.2016.06.018

  日期：2016.7

  A new synthetic protocol of 1-arylpropyne was developed by taking advantage of 1-(diphenylphosphoryl)propyne as propyne equivalent in Sonogashira coupling: consecutive subjection of phosphorylpropyne to t-BuOK and to aryl halides in the presence of Pd and Cu catalysts afforded the corresponding 1-arylpropynes. The following olefination of the 1-arylpropyne with aldehyde provided the corresponding diarylenyne. When the enynes thus obtained were irradiated with UV light, they showed strong emission in organic solvents and in the solid states. In solution, Ph2N-substituted enynes exhibited remarkable solvatofluorochromism, and Lippert-Mataga plot analysis demonstrated that they undergo the larger polarization in the excited states than in the ground states. (C) 2016 Elsevier Ltd. All rights reserved.
• Miljanić, Ognjen Š.; Vollhardt, K. Peter C.; Whitener, Glenn D., Synlett, 2003, # 1, p. 29 - 34
  作者：Miljanić, Ognjen Š.、Vollhardt, K. Peter C.、Whitener, Glenn D.

  DOI：——

  日期：——
• Syntheses and Properties of Medium-Sized Metacyclophanediynes
  作者：Matthias Ramming、Rolf Gleiter

  DOI：10.1021/jo970327r

  日期：1997.8.1

  The syntheses of [11]metacyclophane-2,9-diyne (3), [4.4]metacyclophane-2,12-diyne (4), [4.4]orthometacyclophane-2,12-diyne (5), (Z)-[10]metacyclophane-5-ene-2,8-diyne (6), [10]metacyclophane-2,8-diyne (7), and 5-isopropylidene[9]metacyclophane-2,7-diyne (8) have been achieved. The systems could be stabilized by protecting the triple bonds in 3-8 with the Co-2(CO)(6) moiety. PE spectroscopic investigations of 3 and 6-8 gave no clear-cut evidence for homoconjugative interactions among the pi fragments. The triple bonds in 3-8 could be transformed into the corresponding cis double bands by applying 2-5 molar equiv of Schwartz's reagent (28). Treatment of 3, 4, and ? with t-BuOK allows the transformation of the propargylic moieties into allenic moieties, whereas the same treatment of 5 and 6 transforms the 2-butynyl bridges into 1,3-butadiene bridges, giving rise to several isomers. The structural assignments of 3-8 and their reaction products are based an their spectroscopic properties.