1,2-bis[3-hydroxyphenyl]ethyne

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,2-bis[3-hydroxyphenyl]ethyne
• 英文别名: 3,3'-(ethyn-1,2-diyl)diphenol；bis(m-hydroxyphenyl)acetylene；1,2-bis-(3-hydroxyphenyl)ethyne；3-[2-(3-hydroxyphenyl)ethynyl]phenol
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: GGUCXXQETOSSRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,2-bis[3-hydroxyphenyl]ethyne 在 potassium permanganate 、 sodium carbonate 、 magnesium sulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 3,3-二羟基苄基
  参考文献：
  名称：

  Design and synthesis of cyclic acylguanidines as BACE1 inhibitors

  摘要：

  Based on the lead compound 1 reported in literature, a series of novel BACE1 inhibitors were designed and synthesized, among which compound 11 exhibited a 14-fold improvement in potency over the lead compound 1. This represents a good lead for the discovery of more promising BACE1 inhibitors for the potential treatment of AD. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2015.07.020
• 作为产物：
  描述：

  1-甲氧基-3-[2-(3-甲氧基苯基)乙炔基]苯 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以28%的产率得到1,2-bis[3-hydroxyphenyl]ethyne
  参考文献：
  名称：

  Synthesis of symmetrical diarylalkynes by double stille coupling of bis(tributylstannyl)acetylene

  摘要：

  Treatment of bis(tributylstannyl)acetylene with two equivalents of an aryl iodide in the presence of tetrakis(triphenylphosphine)palladium (0) affords good yields of the symmetrical diarylalkyne. This approach provides a convenient and safe alternative to the use of acetylene in the preparation of these compounds.

  DOI：

  10.1016/s0040-4039(00)75982-x

文献信息

• A Two-Component Alkyne Metathesis Catalyst System with an Improved Substrate Scope and Functional Group Tolerance: Development and Applications to Natural Product Synthesis
  作者：Sebastian Schaubach、Konrad Gebauer、Felix Ungeheuer、Laura Hoffmeister、Marina K. Ilg、Conny Wirtz、Alois Fürstner

  DOI：10.1002/chem.201601163

  日期：2016.6.13

  standard catalyst 1 largely failed to effect the critical macrocyclization, whereas the two‐component system was fully operative. A study directed toward the quinolizidine alkaloid lythrancepine I features yet another instructive example, in that a triyne substrate was metathesized with the help of 3/11 such that two of the triple bonds participated in ring closure, while the third one passed uncompromised

  尽管具有三芳基硅烷醇酸酯配体的钼亚烷基络合物（例如1）是炔烃复分解的极佳催化剂，但当给定底物中存在（多个）质子位点和/或需要施加强迫条件时，它们可能会遇到限制。在这种情况下，将三亚氨基lybenum亚烷基配合物3与易得的三硅烷醇衍生物8或11混合后就地形成催化剂。显示出明显更好的性能。该双组分系统适用于一系列包含伯，仲或酚-OH基团的模型化合物，以及一系列具有挑战性的（双）炔丙基底物。从应用到整个合成中，manshurolide，具有激酶抑制活性的高应变倍半萜内酯和结构上要求严格的免疫抑制性环二炔邻苯二酚A的应用，也证明了其卓越的效率。在这两种情况下，标准催化剂1在很大程度上都无法实现关键的大环化反应，而两组分系统则完全起作用。针对喹唑烷生物碱lythrancepine I的一项研究具有另一个说明性的例子，其中三炔的底物在3的帮助下被易位/ 11，使得三键中的两个参与了环的闭合，而第三个则
• Highly Active Multidentate Catalysts for Efficient Alkyne Metathesis
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE

  公开号：US20130261295A1

  公开（公告）日：2013-10-03

  The invention relates to highly active and selective catalysts for alkyne metathesis. In one aspect, the invention includes a multidentate organic ligand wherein one substrate-binding site of the metal center is blocked. In another aspect, the invention includes N-quaternized or silane-based multidentate organic ligands, capable of binding to metals. In yet another aspect, the invention includes N-quaternized or silane-based multidentate catalysts. The catalysts of the invention show high robustness, strong resistance to small alkyne polymerization and significantly enhanced catalytic activity compared to their corresponding non-quaternized or non-silane-based multidentate catalyst analogues.

  该发明涉及用于炔烃交换反应的高活性和选择性催化剂。在一个方面，该发明包括一种多齿有机配体，其中金属中心的一个底物结合位点被阻塞。在另一个方面，该发明包括N-季铵化或硅基多齿有机配体，能够与金属结合。在另一个方面，该发明包括N-季铵化或硅基多齿催化剂。该发明的催化剂表现出高稳定性，对小炔烃聚合具有很强的抵抗力，并且与其对应的非季铵化或非硅基多齿催化剂类似物相比，具有显着增强的催化活性。
• Multidentate Triphenolsilane-Based Alkyne Metathesis Catalysts
  作者：Haishen Yang、Zhenning Liu、Wei Zhang

  DOI：10.1002/adsc.201201105

  日期：2013.3.25

  propylidyne catalysts has been developed, which are resistant to small alkyne polymerization and compatible with various functional groups (including phenol substrates). The catalysts remain active in solution for days at room temperature (months at −30 °C). The catalysts are also compatible with 5 Å molecular sieves (small alkyne scavengers), and have enabled the homodimerization of small alkyne substrates

  已经开发了一系列三酚硅烷配位的钼（VI）丙炔催化剂，该催化剂可抵抗小型炔烃聚合反应并与各种官能团（包括酚底物）兼容。催化剂在室温下在溶液中保持活性数天（在-30°C时数月）。该催化剂还与5Å分子筛（小型炔烃清除剂）兼容，并能够在封闭系统中于40–70°C下使小型炔烃底物均二聚，二聚体产物的收率达76–96％。还以克级制备了形状持久的亚芳基亚炔基大环（11），催化剂负载量为0.5 mol％，几乎可以定量收率。
• Reaction of Alkyne Having Hydroxyphenyl Group with Mo(CO)₆
  作者：Naotake Kaneta、Tomoe Hirai、Miwako Mori

  DOI：10.1246/cl.1995.627

  日期：1995.8

  The reaction of m-and p-hydroxyphenylpropyne, 1a and 1b, with Mo(CO)6 (5 mol%) affords metathesis products, 2a and 2b, in 78% and 14% (conversion yield, 78%) yields, respectively. However, o-hydroxyphenylpropyne 1f gave trimerization product 4 in 65% yield.

  间和对羟基苯基丙炔 1a 和 1b 与 Mo(CO)6（5 摩尔%）反应，生成的偏合成产物 2a 和 2b，收率分别为 78% 和 14%（转化率，78%）。然而，邻羟基苯丙炔 1f 的三聚产物 4 的收率为 65%。
• Liquid crystalline compounds
  申请人：Rolic AG

  公开号：US06630076B1

  公开（公告）日：2003-10-07

  A compound of formula (I): wherein MG1 and MG3 each independently represent an optionally-substituted aliphatic group with 1 to 80 C-atoms, in which one or more C-atoms may be replaced by a heteroatom, in such a way that oxygen atoms are not linked to one another; or an optionally-substituted aromatic or non-aromatic carbocyclic or heterocyclic ring system, with 1 to 80 C-atoms; and MG2 represents a group comprising at least two and up to four optionally-substituted aromatic or non-aromatic carbocyclic or heterocyclic ring systems, with 1 to 80 C-atoms, wherein, when MG2 represents a group comprising four optionally-substituted ring systems, at least three of the ring systems are aligned in between B1 and B2. The groups MG1, MG2 and MG3 in these new “staircase molecules” may be selected so that each one has one or more of the properties which are required in an LCP material prepared by polymerizing the compound.

  式(I)的化合物：其中MG1和MG3各自独立地表示具有1到80个C原子的可选取代脂肪基，其中一个或多个C原子可以被杂原子取代，以使氧原子不相互连接；或具有1到80个C原子的可选取代芳香族或非芳香族碳环或杂环系统；而MG2表示包含至少两个且最多四个可选取代的芳香族或非芳香族碳环或杂环系统，其具有1到80个C原子，其中，当MG2表示包含四个可选取代的环系统时，至少三个环系统位于B1和B2之间。这些新的“楼梯分子”中的MG1、MG2和MG3基团可以被选择为每个基团具有在聚合化合物制备的LCP材料中所需的一个或多个性质。