3,3,6,6-tetramethyl-9-(4-(prop-2-ynyloxy)phenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3,6,6-tetramethyl-9-(4-(prop-2-ynyloxy)phenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
• 英文别名: 3,3,6,6-tetramethyl-9-[4-(prop-2-yn-1-yloxy)phenyl]-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione；3,3,6,6-tetramethyl-9-(4-prop-2-ynoxyphenyl)-4,5,7,9-tetrahydro-2H-xanthene-1,8-dione
• 化学式: C₂₆H₂₈O₄
• 分子量: 404.506
• InChiKey: HKNROVCTQHBSLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-叠氮甲苯 、 3,3,6,6-tetramethyl-9-(4-(prop-2-ynyloxy)phenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione 在 copper(II) oxide 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 1.0h， 以78%的产率得到3,3,6,6-tetramethyl-9-(4-((1-p-tolyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry

  摘要：

  Copper(II) oxide (CuO) nanoparticles have been found to be an efficient catalyst for 1,3-dipolar cycloaddition (CuAAC) of aromatic azides and acetylenic xanthenes furnishing the corresponding xanthene substituted triazoles in excellent yields. CuO nanoparticles have been synthesized from copper acetate by simple co-precipitation method and characterized by scanning electron microscope, energy dispersive X-ray analysis, transmission electron microscope, and X-ray diffraction analysis. The salient features of the present protocol are mild reaction conditions, shorter reaction time, reusability of the catalyst, and applicability to a wide range of substrates. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.016
• 作为产物：
  描述：

  对羟基苯甲醛 在 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 25.5h， 生成 3,3,6,6-tetramethyl-9-(4-(prop-2-ynyloxy)phenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
  参考文献：
  名称：

  铬烯-二氢嘧啶酮和呫吨-二氢嘧啶酮杂化物：设计、合成以及抗菌和抗生物膜活性

  摘要：

  一系列 11 种色烯-二氢嘧啶酮和 11 种呫吨-二氢嘧啶酮杂化化合物通过连续的多组分反应，然后是铜催化的炔烃-叠氮化物环加成反应，很容易合成。杂种的抗生物膜和抗菌活性针对金黄色葡萄球菌和铜绿假单胞菌进行了评估，抗生物膜特性呈剂量依赖性。大多数化合物显示出对金黄色葡萄球菌的抗生物膜活性，而不抑制其生长。在体内，蠕虫急性或长期暴露于15a杂种表现出存活率、育雏大小和体长下降以及凋亡尸体数量增加；然而，这些影响仅在测试的最高浓度下观察到。计算机分析表明，该分子在 SOS 通路中有一个新的靶标，用于诱导 DNA 损伤修复。因此，这些杂化物是很有前途的化合物，可以对抗与难以治疗的慢性感染相关的细菌生物膜。

  DOI：

  10.1039/d2nj05211c

文献信息

• Copper-hydroxyacetophenone thiosemicarbazone complex on silica-coated magnetite nanoparticles as an efficient catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles
  作者：Narjes Kaviani、Somayeh Behrouz、Abbas Ali Jafari、Mohammad Navid Soltani Rad

  DOI：10.1016/j.jorganchem.2024.123043

  日期：2024.3

  Synthesis, characterization, and application of copper-hydroxyacetophenone thiosemicarbazone complex immobilized on silica-coated magnetite nanoparticles (FeO@SiO-HAT-Cu(I)) as a novel magnetically retrievable nanocatalyst for the three-component synthesis of 1,4-disubstituted 1,2,3-triazoles are described. [Display omitted]

  二氧化硅包覆磁铁矿纳米颗粒（FeO@SiO-HAT-Cu(I)）固定铜-羟基苯乙酮缩氨基硫脲复合物的合成、表征及应用作为新型磁性可回收纳米催化剂用于1,4-二取代1的三组分合成描述了2,3-三唑。[显示省略]
• CuO nanoparticles: synthesis and application as an efficient reusable catalyst for the preparation of xanthene substituted 1,2,3-triazoles via click chemistry
  作者：P. Iniyavan、G.L. Balaji、S. Sarveswari、V. Vijayakumar

  DOI：10.1016/j.tetlet.2015.07.016

  日期：2015.8

  Copper(II) oxide (CuO) nanoparticles have been found to be an efficient catalyst for 1,3-dipolar cycloaddition (CuAAC) of aromatic azides and acetylenic xanthenes furnishing the corresponding xanthene substituted triazoles in excellent yields. CuO nanoparticles have been synthesized from copper acetate by simple co-precipitation method and characterized by scanning electron microscope, energy dispersive X-ray analysis, transmission electron microscope, and X-ray diffraction analysis. The salient features of the present protocol are mild reaction conditions, shorter reaction time, reusability of the catalyst, and applicability to a wide range of substrates. (C) 2015 Elsevier Ltd. All rights reserved.
• Chromene-dihydropyrimidinone and xanthene-dihydropyrimidinone hybrids: design, synthesis, and antibacterial and antibiofilm activities
  作者：Samuel J. Santos、Fernanda C. P. Rossatto、Natália S. Jardim、Daiana S. Ávila、Rodrigo Ligabue-Braun、Luiz A. M. Fontoura、Karine R. Zimmer、Dennis Russowsky

  DOI：10.1039/d2nj05211c

  日期：——

  A series of eleven chromene-dihydropyrimidinone and eleven xanthene-dihydropyrimidinone hybrid compounds were easily synthesized through a sequential multicomponent reaction followed by copper-catalyzed alkyne–azide cycloaddition reaction. The antibiofilm and antibacterial activities of hybrids were evaluated against Staphylococcus aureus and Pseudomonas aeruginosa and the antibiofilm property was

  一系列 11 种色烯-二氢嘧啶酮和 11 种呫吨-二氢嘧啶酮杂化化合物通过连续的多组分反应，然后是铜催化的炔烃-叠氮化物环加成反应，很容易合成。杂种的抗生物膜和抗菌活性针对金黄色葡萄球菌和铜绿假单胞菌进行了评估，抗生物膜特性呈剂量依赖性。大多数化合物显示出对金黄色葡萄球菌的抗生物膜活性，而不抑制其生长。在体内，蠕虫急性或长期暴露于15a杂种表现出存活率、育雏大小和体长下降以及凋亡尸体数量增加；然而，这些影响仅在测试的最高浓度下观察到。计算机分析表明，该分子在 SOS 通路中有一个新的靶标，用于诱导 DNA 损伤修复。因此，这些杂化物是很有前途的化合物，可以对抗与难以治疗的慢性感染相关的细菌生物膜。