2,2'-((4-hydroxyphenyl)methylene)bis(3-hydroxycyclohex-2-en-1-one) | 497058-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2'-((4-hydroxyphenyl)methylene)bis(3-hydroxycyclohex-2-en-1-one)
• 英文别名: 3-Hydroxy-2-[(2-hydroxy-6-oxocyclohexen-1-yl)-(4-hydroxyphenyl)methyl]cyclohex-2-en-1-one
• CAS: 497058-26-1
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: AMDNSKKCLDFWSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 对羟基苯甲醛 在 lipase from Thermomyces lanuginosus, immobilized on particle silica gel 作用下， 以 正己烷 为溶剂， 反应 16.0h， 以90%的产率得到2,2'-((4-hydroxyphenyl)methylene)bis(3-hydroxycyclohex-2-en-1-one)
  参考文献：
  名称：

  混杂酶催化的级联反应：x吨酮衍生物的合成

  摘要：

  在筛选生物催化剂和反应条件（包括有机溶剂，水含量，脂肪酶负载，反应温度和时间）后，脂肪酶TLIM对于1,3-二酮与芳族醛的Knoevenagel-Michael级联反应显示出明显的混杂性，从而合成了蒽酮衍生物。该程序具有令人满意的优点，例如环境开始，简单的后处理，通用性，获得优异的收率（80-97％）以及生物催化剂的回收潜力。

  DOI：

  10.1016/j.bioorg.2018.06.034

文献信息

• Nano Fe/NaY zeolite: an efficient and reusable solid-supported catalyst for synthesis of 1-oxo-hexahydroxanthene and tetraketone derivatives
  作者：Mahmood Tajbakhsh、Marzieh Heidary、Rahman Hosseinzadeh

  DOI：10.1007/s11164-015-2094-2

  日期：2016.2

  iron oxide (up to 32.8 %) with average diameter of 30–40 nm on the surface of NaY zeolite. The catalytic activity of nano Fe/NaY zeolite was examined in the preparation of 1-oxo-hexahydroxanthene and tetraketone derivatives. The results showed its applicability as a green, reusable, and promising catalyst for organic synthesis. This protocol demonstrates several notable advantages including short reaction

  摘要 通过离子交换技术在室温下成功合成了高铁离子含量的纳米Fe / NaY沸石。制备的Fe / NaY的特征在于X射线衍射，扫描电子显微镜，能量色散X射线光谱，Brunauer-Emmett-Teller（BET）表面积测量和傅立叶变换红外（FT-IR）光谱。数据分析证实，NaY沸石表面上存在平均直径为30–40 nm的氧化铁（高达32.8％）。在制备1-氧代六氢氧杂蒽和四酮衍生物时，研究了纳米Fe / NaY沸石的催化活性。结果表明其可作为绿色，可重复使用且有前途的有机合成催化剂。该协议展示了几个显着的优势，包括反应时间短，环境友好的条件，无需萃取或色谱纯化步骤，更方便的后处理，高收率的产品以及无需使用任何有害溶剂。回收催化剂并连续使用多达四次，而催化活性没有明显损失。 图形概要
• Selective and highly efficient synthesis of xanthenedione or tetraketone derivatives catalyzed by ZnO nanorod-decorated graphene oxide
  作者：Sepideh Hasanzadeh Banakar、Mohammad G. Dekamin、Amene Yaghoubi

  DOI：10.1039/c8nj01053f

  日期：——

  ZnO nanorod-decorated graphene oxide (GO/ZnO), containing Lewis and Bronsted acid centers, was introduced as a selective, highly efficient and recoverable nanocatalyst for the pseudo three-component synthesis of diverse tetraketone or xanthenedione derivatives via condensation of aromatic aldehydes with 1,3-dicarbonyl compounds in short reaction times and good to excellent yields in H2O under refluxing

  包含路易斯和布朗斯台德酸中心的ZnO纳米棒修饰的氧化石墨烯（GO / ZnO）被引入作为一种选择性，高效且可回收的纳米催化剂，用于通过芳香醛与1的缩合反应合成各种四酮或黄二酮衍生物的假三组分。，3-二羰基化合物的反应时间短，在H 2中的收率好至极好O分别在回流和无溶剂条件下进行。此外，GO / ZnO纳米复合材料已被回收并重复使用至少四次，而其活性并未显着降低。催化剂的低负荷，高至优异的产率，消除了用于修饰催化剂的任何有毒重金属或腐蚀性试剂，产品的简单分离和纯化以及催化剂的可重复使用性是此绿色方案的最重要优势。
• Zinc‐containing ionic liquid as a dual solvent‐catalyst in base‐free condensations under ultrasonic irradiation
  作者：Hossein Ghafuri、Soheila Yaghoubi、Hamid Reza Esmaili Zand

  DOI：10.1002/aoc.5149

  日期：2019.10

  nature was synthesized with melting point of 76 °C by a facile method. The synthesized [Caff‐TEA]+[ZnBr3]− has high catalytic activity as both of catalyst and solvent in condensation reactions for the synthesis of benzylidenes, bis‐hydroxyenones and xanthenes. Synthesized IL was characterized by proton nuclear magnetic resonance (1HNMR), Fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction

  在这项研究中，合成了使用咖啡因（Caff），三苯胺（TEA）和ZnBr 2，[Caff‐TEA] + [ZnBr 3 ] -的天然离子液体，该液体具有高催化活性和环境友好性通过简便的方法将其熔点定为76°C。合成的[Caff‐TEA] + [ZnBr 3 ] -在缩合反应中作为催化剂和溶剂具有很高的催化活性，用于合成亚苄基，双羟基烯酮和黄嘌呤。合成的IL的特征在于质子核磁共振（1HNMR），傅立叶变换红外光谱（FT-IR），X射线衍射（XRD）和能量色散X射线光谱（EDX）分析。合成的杂环还通过FT-IR，质子核磁共振（1 HNMR）和碳核磁共振（13 CNMR）进行表征。
• 1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers as an efficient and reusable nanocatalyst for the synthesis of tetraketones in aqueous medium
  作者：Zahra Lasemi、Mahmood Tajbakhsh、Heshmatoallah Alinezhad、Forough Mehrparvar

  DOI：10.1007/s11164-020-04167-y

  日期：2020.7

  1,8-Diazabicyclo [5.4.0] undec-7-ene functionalized cellulose nanofibers (CNF@DBU[Cl]) were simply prepared and characterized by analytical techniques. Scanning electron microscope confirmed that CNF@DBU[Cl] was formed with average size of 30–60 nm. X-ray diffraction of CNF@DBU[Cl] showed that the crystalline structure of the cellulose nanofibers was remained unchanged after functionalization. According to elemental analyses and thermal gravimetric analysis, the loading amount of organic group on cellulose nanofibers was found to be 1.46 mmol/g. The catalytic activity of DBU functionalized cellulose nanofibers was studied for the synthesis of biologically important tetraketone derivatives in the reaction of aldehydes with 1,3-dicarbonyl compounds. In the presence of CNF@DBU[Cl], the corresponding tetraketones were obtained in 80–96% yields under very mild reaction conditions. The catalyst was recovered and reused four successive runs without significant loss of catalytic activity. This method showed several significant advantages including short reaction times, high yields of products, use of various substrates, convenient work-up, no necessity of extraction or chromatographic purification steps, environmentally friendly conditions and lack of use of any harmful solvent.

  简单制备了1,8-二氮杂双环[5.4.0]十一-7-烯功能化纤维素纳米纤维（CNF@DBU[Cl]），并通过分析技术对其进行了表征。扫描电子显微镜证实，CNF@DBU[Cl]的平均粒径为30-60 nm。CNF@DBU[Cl] 的 X 射线衍射表明，功能化后纤维素纳米纤维的晶体结构保持不变。根据元素分析和热重分析，发现有机基团在纤维素纳米纤维上的负载量为 1.46 mmol/g。研究了 DBU 功能化纤维素纳米纤维在醛与 1,3-二羰基化合物反应中合成具有生物重要意义的四酮衍生物的催化活性。在 CNF@DBU[Cl]存在下，在非常温和的反应条件下，相应四酮的产率为 80-96%。催化剂可回收并连续重复使用四次，催化活性没有明显下降。该方法具有多个显著优点，包括反应时间短、产物收率高、可使用多种底物、操作方便、无需萃取或色谱纯化步骤、环境友好且不使用任何有害溶剂。
• Rapid one pot synthesis of xanthene derivatives by an efficient and reusable nano-ZnAl2O4 – An insight into a new process
  作者：Triveni Rajashekhar Mandlimath、Balijapalli Umamahesh、Kulathu I. Sathiyanarayanan

  DOI：10.1016/j.molcata.2014.04.030

  日期：2014.9

  Nano-ZnAl2O4 was synthesized by blending metal-citrate complex-acrylamide polymer using the precursor method. Powder X-ray diffraction analysis of the catalyst affirmed that the spinel oxide was phase pure. Elemental analysis was confirmed by Energy Dispersive X-ray analysis. Transmission Electron Microscopic (TEM) analysis and Scherrer's formula revealed that the particles were found to be in the order of 20 nm in size. Thermal stability of the catalyst was analyzed by thermogravimetric and differential thermal analysis (TG-DTA). Total acidity of the nano-ZnAl2O4 evaluated by NH3-TPD was 8.8 mmol NH3/g. Diversity in the synthesis of xanthene derivatives was investigated using nanozinc aluminate as a catalyst. Nanoform of the catalyst showed better activity than the bulk form due to its large surface area 50 m(2)/g. The 2,2'-arylmethylene bis (3-hydroxy-2-cyclohexene-1-one), 2,2'-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and 1-Oxo-hexahydroxanthenes were synthesized rapidly using ZnAl2O4 and the catalyst was successfully recycled without any loss of activity. (C) 2014 Elsevier B.V. All rights reserved.