2,5-di(hex-1-yn-1-yl)benzene-1,4-diol | 925900-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-di(hex-1-yn-1-yl)benzene-1,4-diol
• 英文别名: 2,5-Bis(hex-1-ynyl)benzene-1,4-diol
• CAS: 925900-81-8
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: BPAGTGFXGTXGPF-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  438.4±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-di(hex-1-yn-1-yl)benzene-1,4-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 乙烯 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4,9-bis(1'-butylethenyl)-2,7-dihydrobenzo[1,2-b:4,5-b']dipyran
  参考文献：
  名称：

  An efficient synthesis of fused tricycles with a benzene core via intramolecular double ring-closing enyne metathesis

  摘要：

  A double enyne metathesis reaction has been developed for the efficient synthesis of tricyclic products with a benzene core in good yields. By this protocol, bisannulated benzenes with different ring sizes may he simultaneously constructed from the corresponding precursors in just 'one shot'. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.016
• 作为产物：
  描述：

  1,4-Dibrom-2,5-diacetoxybenzol 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成 2,5-di(hex-1-yn-1-yl)benzene-1,4-diol
  参考文献：
  名称：

  An efficient synthesis of fused tricycles with a benzene core via intramolecular double ring-closing enyne metathesis

  摘要：

  A double enyne metathesis reaction has been developed for the efficient synthesis of tricyclic products with a benzene core in good yields. By this protocol, bisannulated benzenes with different ring sizes may he simultaneously constructed from the corresponding precursors in just 'one shot'. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.016

文献信息

• Double annulations of dihydroxy- and diacetoxy-dialkynylbenzenes. An efficient construction of benzodifurans
  作者：Zhiqiang Liang、Shengming Ma、Jihong Yu、Ruren Xu

  DOI：10.1016/j.tet.2007.10.051

  日期：2007.12

  An efficient synthetic route to construct disubstituted benzodifurans from dihydroxy- or diacetoxy-dialkynylbenzenes utilizing Cs2CO3 or Pd(OAc)2/Cs2CO3 promoted double annulations is described. The scope for the reaction in the presence of a catalytic amount of Pd(OAc)2 is more general. In addition, it was observed that NaOH-promoted reaction of diacetoxy-dialkynylbenzenes may directly afford in THF/MeOH/H2O

  描述了一种利用Cs 2 CO 3或Pd（OAc）2 / Cs 2 CO 3促进的双环法从二羟基-或二乙酰氧基-二炔基苯构建二取代的苯并呋喃的有效合成途径。在催化量的Pd（OAc）2存在下反应的范围更一般。此外，已观察到，NaOH促进的二乙酰氧基-二炔基苯的反应可以在80°C的苯并二呋喃中以单锅法通过水解和双环化直接在THF / MeOH / H 2 O中提供。但是，在大多数情况下，反应的选择性较低，提供了双环化产物和单环化-水解产物的混合物。
• Palladium-Catalyzed Double Annulations To Construct Multisubstituted Benzodifurans
  作者：Zhiqiang Liang、Shengming Ma、Jihong Yu、Ruren Xu

  DOI：10.1021/jo7016263

  日期：2007.11.1

  Efficient synthetic routes to construct multisubstituted benzo[1,2-b:5,4-b‘]difurans and benzo[1,2-b:4,5-b‘]difurans from bis(allyloxy)bis(alkynyl)benzenes or bis(alkynyl)dihydroxybenzenes and allylic halides utilizing palladium-catalyzed double annulations is reported. By further applying a double ring-closing metathesis reaction, pentacyclic compounds were also prepared.

  有效的合成路线来构建多取代苯并[1,2- b：5,4- b “] difurans和苯并[1,2- b：4,5- b ”]由二difurans（烯丙氧基）双（炔基）苯或据报道，利用钯催化的双环双（炔基）二羟基苯和烯丙基卤化物。通过进一步进行双闭环复分解反应，还制备了五环化合物。
• Enantioselective Synthesis of Planar Chiral Zigzag-Type Cyclophenylene Belts by Rhodium-Catalyzed Alkyne Cyclotrimerization
  作者：Juntaro Nogami、Yusuke Tanaka、Haruki Sugiyama、Hidehiro Uekusa、Atsuya Muranaka、Masanobu Uchiyama、Ken Tanaka

  DOI：10.1021/jacs.0c03684

  日期：——

  planar chiral zigzag-type [8]CP belt revealed that the unevenness of the molecules meshes with each other to form a one-dimensional columnar packing structure, in which one column contains single enantiomers, giving two types of chiral columns [(S) and (R)-form columns] arranged alter-nately. The ring strain of the zigzag-type [8]CP belt was smaller than that of the armchair-type [8]CPP belt despite

  平面手性锯齿形 [8] 和 [12] 环亚苯基 (CPs) 带已通过铑催化的相应环状聚炔的对映选择性分子内顺序环三聚反应以良好的收率合成，ee 值分别高达 98% 和 83% . 观察到的高对映选择性源于不对称三炔单元的区域选择性形成红花环中间体。外消旋平面手性锯齿形[8]CP带的X射线晶体结构分析表明，分子的不均匀性相互啮合形成一维柱状填充结构，其中一根柱子含有单个对映体，给出两种手性柱[(S)和(R)型柱]交替排列。尽管环尺寸较小，但锯齿形 [8]CP 带的环应变小于扶手椅型 [8]CPP 带的环应变，这是由于存在应变消除的间三联苯部分。由于间亚苯基部分的 π 共轭中断，锯齿形 CP 带的苯环数量对吸收和发射峰的影响很小。然而，绝对荧光量子产率以及吸收和发射峰的弯曲效应是显着的。关于手性特性，在 [8]CP 带中观察到 ECD 和 CPL 的适度各向异性不对称因子。由于间亚苯基部分的 π
• Synthesis of Belt- and Möbius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization
  作者：Shuhei Nishigaki、Yu Shibata、Atsuya Nakajima、Hajime Okajima、Yui Masumoto、Taisei Osawa、Atsuya Muranaka、Haruki Sugiyama、Ayano Horikawa、Hidehiro Uekusa、Hiroyuki Koshino、Masanobu Uchiyama、Akira Sakamoto、Ken Tanaka

  DOI：10.1021/jacs.9b06197

  日期：2019.9.25

  high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This Möbius-shaped [10]CPP possesses stable chirality and isolated with high enantiomeric purity. It is evident from the reaction Gibbs energy calculation that the above irreversible cyclotrimerizations are highly exothermic; therefore establishing that the intramolecular alkyne cyclotrimerization

  带状 [8] 环对亚苯基 (CPP) 和对映体富集的莫比乌斯形 [10]CPP 分别通过高产率铑催化的环状十二烷和十五烷的分子内环三聚反应合成。这种莫比乌斯形 [10]CPP 具有稳定的手性并以高对映体纯度分离。从反应吉布斯能量计算可以看出，上述不可逆环三聚反应是高度放热的；因此，确定分子内炔烃环三聚是一种有效的拉紧环状分子带的途径。
• An efficient synthesis of fused tricycles with a benzene core via intramolecular double ring-closing enyne metathesis
  作者：Zhiqiang Liang、Shengming Ma、Jihong Yu、Ruren Xu

  DOI：10.1016/j.tet.2006.11.016

  日期：2007.1

  A double enyne metathesis reaction has been developed for the efficient synthesis of tricyclic products with a benzene core in good yields. By this protocol, bisannulated benzenes with different ring sizes may he simultaneously constructed from the corresponding precursors in just 'one shot'. (c) 2006 Elsevier Ltd. All rights reserved.