2,4-dibromo-6-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol | 1262020-28-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,4-dibromo-6-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol
• 英文别名: 2,4-Dibromo-6-(1-hydroxy-3-phenylprop-2-ynyl)phenol；2,4-dibromo-6-(1-hydroxy-3-phenylprop-2-ynyl)phenol
• CAS: 1262020-28-9
• 化学式: C₁₅H₁₀Br₂O₂
• 分子量: 382.051
• InChiKey: NWWDODBOUZHJIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2,4-dibromo-6-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol 在 manganese(IV) oxide 、 tricyclohexylphosphine-silver chloride 、 N,N-二异丙基乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 生成 (2Z)-2-benzylidene-5,7-dibromo-1-benzofuran-3-one
  参考文献：
  名称：

  Water-Promoted, Silver–Phosphine Complex–Catalyzed Stereoselective Cyclization of 2-(1-Hydroxy-3-arylprop-2-ynyl)phenols Leading to a Highly Efficient Approach to Aurones

  摘要：

  Silver-phosphine complexes can be utilized as highly efficient catalysts for the cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols (1) to give product 2, key intermediates to synthesize aurones (4), with good yields and stereoselectivities in water-toluene mixed solvent. With fluoride as the counteranion, complete E- or Z-stereoselectivities were achieved at high temperature or room temperature, respectively. Furthermore, after removing water from the reaction mixtures, the toluene solution containing crude products 2 can be treated by MnO2 directly without further purification, to give aurones 4 in good yields.

  DOI：

  10.1080/00397911.2010.517613
• 作为产物：
  描述：

  3,5-二溴水杨醛 、 苯乙炔 生成 2,4-dibromo-6-(1-hydroxy-3-phenylprop-2-yn-1-yl)phenol
  参考文献：
  名称：

  Water-Promoted, Silver–Phosphine Complex–Catalyzed Stereoselective Cyclization of 2-(1-Hydroxy-3-arylprop-2-ynyl)phenols Leading to a Highly Efficient Approach to Aurones

  摘要：

  Silver-phosphine complexes can be utilized as highly efficient catalysts for the cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols (1) to give product 2, key intermediates to synthesize aurones (4), with good yields and stereoselectivities in water-toluene mixed solvent. With fluoride as the counteranion, complete E- or Z-stereoselectivities were achieved at high temperature or room temperature, respectively. Furthermore, after removing water from the reaction mixtures, the toluene solution containing crude products 2 can be treated by MnO2 directly without further purification, to give aurones 4 in good yields.

  DOI：

  10.1080/00397911.2010.517613

文献信息

• Cu(OAc)₂·H₂O-Promoted Tandem β-Alkynyl Elimination of α- or β-Hydroxy Propargylic Alcohols and Homocoupling of the Resulting Alkynyl Species
  作者：Xiangsheng Xu、Zhenyong Huang、Yanfeng Lu

  DOI：10.3184/174751913x13739011239995

  日期：2013.9

  α or β-hydroxy propargylic alcohols undergo tandem C(sp)–C(sp3) bond cleavage via β-alkynyl elimination and homo-coupling of the resulted alkynyl species in the presence of Cu(OAc)2·H2O to produce the corresponding hydroxycarbonyl compounds and 1,3-butadiynes.

  α 或 β-羟基炔丙醇在 Cu(OAc)2·H2O 存在下通过 β-炔基消除和所得炔基的均偶联发生串联 C(sp)–C(sp3) 键断裂，生成相应的羟基羰基化合物和 1,3-丁二炔。
• Mycobacterial protein tyrosine kinase, PtkA phosphorylates PtpA at tyrosine residues and the mechanism is stalled by the novel series of inhibitors
  作者：Swati Jaiswal、Aditi Chatterjee、Sapna Pandey、Kiran Lata、Ranjith Kumar Gadi、Rajesh Manda、Sanjay Kumar、Maddi Sridhar Reddy、Ravishankar Ramachandran、Kishore K. Srivastava

  DOI：10.1080/1061186x.2018.1473407

  日期：2019.1.2

  roles in mycobacterial survival and in its pathogenesis. Mycobacteria evade host immune mechanism by inhibiting phagosome – lysosome fusion in which mycobacterial protein tyrosine phosphatase A (PtpA;TP) plays an indispensable role. Tyrosine kinase (PtkA;TK) activated by autophosphorylation; phosphorylates TP, which subsequently leads to increase in its phosphatase activity. The phosphorylated TP is

  磷酸化和去磷酸化是分枝杆菌生理的关键机制，并且在分枝杆菌的生存及其发病机理中起着关键作用。分枝杆菌通过抑制吞噬体-溶酶体融合来逃避宿主的免疫机制，其中分枝杆菌蛋白酪氨酸磷酸酶A（PtpA; TP）起着不可或缺的作用。酪氨酸激酶（PtkA； TK）被自身磷酸化激活；磷酸化TP，随后导致其磷酸酶活性增加。磷酸化的TP被分泌在巨噬细胞的吞噬体中。在本研究中，我们已经显示了TP的两个位点的磷酸化。Y 128和Y 129对于传统知识介导的磷酸酶活性至关重要。TK和TP之间这种相互作用的破坏抑制了后来的激活，这进一步导致分枝杆菌的细胞内存活率降低。此外，已经使用苄基苯并呋喃和苯并呋喃酰胺建立了概念验证，它们抑制分枝杆菌的生长和细胞内存活，与TP的功能位点相关并与TK竞争。通过在基于同源性的结构模型中观察蛋白质-蛋白质和蛋白质-抑制剂复合物的固定，并通过表面等离振子共振分析，可以进一步重新确定这种结合。
• Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization
  作者：Manda Rajesh、Nuligonda Thirupathi、Thota Jagadeshwar Reddy、Sanjeev Kanojiya、Maddi Sridhar Reddy

  DOI：10.1021/acs.joc.5b02204

  日期：2015.12.18

  An unusual Pd-catalyzed isocyanide assisted 5exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols is achieved for 2-alkyl/benzyl benzofurans. The reaction features a high substrate scope, insensitivity to air, and excellent product yielding. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of thus synthesized 2-benzylfurans are described for azido-, alkoxy-, hydroxyl-, amide-, and tetrazolyl adducts.
• Ligand-promoted reaction on silver nanoparticles: phosphine-promoted, silver nanoparticle-catalyzed cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols
  作者：Min Yu、Mingdeng Lin、Chengyan Han、Li Zhu、Chao-Jun Li、Xiaoquan Yao

  DOI：10.1016/j.tetlet.2010.10.065

  日期：2010.12

  A highly efficient annulation of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols leading to the key intermediates to synthesize aurones was catalyzed by silver nanoparticles/carbon black-supported silver nanoparticles. In the presence of phosphine ligand, both the catalysts show excellent catalytic activities in the reaction and give the products with good yields as well as excellent regio- and stereo-selectivities in a water-toluene mixed solvent. Furthermore, the catalysts can be recovered and recycled effectively several times. (C) 2010 Elsevier Ltd. All rights reserved.
• Water-Promoted, Silver–Phosphine Complex–Catalyzed Stereoselective Cyclization of 2-(1-Hydroxy-3-arylprop-2-ynyl)phenols Leading to a Highly Efficient Approach to Aurones
  作者：Mingdeng Lin、Min Yu、Chengyan Han、Chao-Jun Li、Xiaoquan Yao

  DOI：10.1080/00397911.2010.517613

  日期：2011.11.1

  Silver-phosphine complexes can be utilized as highly efficient catalysts for the cyclization of 2-(1-hydroxy-3-arylprop-2-ynyl)phenols (1) to give product 2, key intermediates to synthesize aurones (4), with good yields and stereoselectivities in water-toluene mixed solvent. With fluoride as the counteranion, complete E- or Z-stereoselectivities were achieved at high temperature or room temperature, respectively. Furthermore, after removing water from the reaction mixtures, the toluene solution containing crude products 2 can be treated by MnO2 directly without further purification, to give aurones 4 in good yields.