1,3-bis(3,4-(methylenedioxy)benzyl) ether | 109600-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1,3-bis(3,4-(methylenedioxy)benzyl) ether
• 英文别名: bis(3,4-(methylenedioxy)benzyl)ether；Di-piperonyl-aether；5,5'-(2-oxa-propane-1,3-diyl)-bis-benzo[1,3]dioxole；5-(1,3-Benzodioxol-5-ylmethoxymethyl)-1,3-benzodioxole
• CAS: 109600-72-8
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: RDGVKXBPKHLLRX-UHFFFAOYSA-N

物化性质

• 沸点：
  410.1±14.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-bis(3,4-(methylenedioxy)benzyl) ether 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.5h， 生成 2,2'-diformyl-4,4',5,5'-bis(methylenedioxy)biphenyl
  参考文献：
  名称：

  Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent

  摘要：

  The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a-e), N-benzyl-N-phenethylamines (2a-c) and N,N-dibenzylamines (3a-e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3. Et2O in CH2Cl2 to give the biaryl coupling products (4-6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12-15), whose side chain moiety could be easily cleaved by the known method to give 2,2'-substituted biphenyl compounds (16-18).

  DOI：

  10.1021/jo980704f
• 作为产物：
  描述：

  trimethylsilyl 3,4-dioxymethylene benzyl ether 在 硫酸 、 silica gel 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以80%的产率得到1,3-bis(3,4-(methylenedioxy)benzyl) ether
  参考文献：
  名称：

  Silica Sulfuric Acid: An Efficient Catalyst for the Direct Conversion of Primary and Secondary Trimethylsilyl Ethers to their Corresponding Ethers under Mild and Heterogeneous Conditions

  摘要：

  在温和且异相的条件下，初级和次级三甲基硅基醚在硅酸硫酸的存在下转化为相应的醚，产率良好至优秀。

  DOI：

  10.1055/s-2003-41469

文献信息

• Synthesis of Cycloveratrylene Macrocycles and Benzyl Oligomers Catalysed by Bentonite under Microwave/Infrared and Solvent-Free Conditions
  作者：René Miranda、Omar Valencia-Vázquez、Carlos Maya-Vega、Inés Nicolás-Vázquez、Yolanda Vargas-Rodriguez、José Morales-Serna、Eréndira García-Ríos、Manuel Salmón

  DOI：10.3390/molecules181012820

  日期：——

  Tonsil Actisil FF, which is a commercial bentonitic clay, promotes the formation of cycloveratrylene macrocycles and benzyl oligomers from the corresponding benzyl alcohols in good yields under microwave heating and infrared irradiation in the absence of solvent in both cases. The catalytic reaction is sensitive to the type of substituent on the aromatic ring. Thus, when benzyl alcohol was substituted with a methylenedioxy, two methoxy or three methoxy groups, a cyclooligomerisation process was induced. Unsubstituted, methyl and methoxy benzyl alcohols yielded linear oligomers. In addition, computational chemistry calculations were performed to establish a validated mechanistic pathway to explain the growth of the obtained linear oligomers.

  Tonsil Actisil FF是一种商业膨润土，在无溶剂的情况下，通过微波加热和红外辐射促进了环苯乙烯大环和相应苯基醇的苄基寡聚物的形成，产率良好。催化反应对于芳环上取代基的类型比较敏感。因此，当苄基醇被甲撑二氧基、两个甲氧基或三个甲氧基取代时，诱导了环状寡聚过程。而未取代的、甲基和甲氧基苄基醇则产生了线性寡聚物。此外，进行了计算化学计算，以建立一个经过验证的机制路径，以解释所获得的线性寡聚物的生长。
• An economical and environmentally friendly oxidative biaryl coupling promoted by activated MnO₂
  作者：Jingjing Yang、Shutao Sun、Ziyu Zeng、Hongbo Zheng、Wei Li、Hongxiang Lou、Lei Liu

  DOI：10.1039/c4ob01409j

  日期：——

  An activated manganese dioxide (MnO2)–BF3·OEt2 oxidation system was developed to efficiently mediate the intramolecular as well as intermolecular biaryl coupling. The oxidative coupling proceeds smoothly at ambient temperature to deliver the corresponding five- to eight-membered tricyclic products in good to excellent yields. The employment of the combination of MnO2 and BF3·OEt2 is attractive on the basis of economical and environmental issues.

  开发了一种活化的二氧化锰（MnO2）–BF3·OEt2氧化系统，能够高效地介导分子内和分子间的二芳基偶联。该氧化偶联在常温下顺利进行，产物为相应的五到八元环三环化合物，产率良好至优秀。基于经济和环境问题，使用 和 ·OEt2的组合具有吸引力。
• METHOD FOR PRODUCING A HIGH-PURITY AROMATIC METHYL ALCOHOL AND HIGH-PURITY AROMATIC METHYL ALCOHOL COMPOSITION HAVING EXCELLENT PRESERVATION STABILITY
  申请人：Doi Takashi

  公开号：US20120323021A1

  公开（公告）日：2012-12-20

  An object of the present invention is to provide a high-purity aromatic methyl alcohol compound having reduced a bis(arylmethyl)ether compound as a side product mixed thereinto and a high-purity aromatic methyl alcohol composition having excellent preservation stability and methods for producing them. The object of the present invention is achieved by a method for producing a high-purity aromatic methyl alcohol compound, which comprises obtaining a high-purity aromatic methyl alcohol compound in high yield from an aromatic methyl alcohol-containing crude product by subjecting the crude product to distillation in the presence of an anti-decomposition agent. Further, the object for the preservation stability is achieved by producing a high-purity aromatic methyl alcohol composition using the obtained high-purity aromatic methyl alcohol compound.

  本发明的目的是提供一种高纯度芳香基甲醇化合物，其中混有减少的双(芳基甲基)醚化合物作为副产物，并且具有良好的保存稳定性的高纯度芳香基甲醇组合物及其生产方法。本发明的目的通过以下方法实现：通过在抗分解剂的存在下对含芳香基甲醇的原始产品进行蒸馏，从而高产率地获得高纯度芳香基甲醇化合物。此外，通过使用获得的高纯度芳香基甲醇化合物生产高纯度芳香基甲醇组合物，实现了保存稳定性的目标。
• METHOD FOR PRODUCING HIGH PURITY AROMATIC METHYL ALCOHOL, AND HIGH PURITY AROMATIC METHYL ALCOHOL COMPOSITION HAVING EXCELLENT STORAGE STABILITY
  申请人：Ube Industries, Ltd.

  公开号：EP2540695A1

  公开（公告）日：2013-01-02

  An object of the present invention is to provide a high-purity aromatic methyl alcohol compound having reduced a bis(arylmethyl) ether compound as a side product mixed thereinto and a high-purity aromatic methyl alcohol composition having excellent preservation stability and methods for producing them. The object of the present invention is achieved by a method for producing a high-purity aromatic methyl alcohol compound, which comprises obtaining a high-purity aromatic methyl alcohol compound in high yield from an aromatic methyl alcohol-containing crude product by subjecting the crude product to distillation in the presence of an anti-decomposition agent. Further, the object for the preservation stability is achieved by producing a high-purity aromatic methyl alcohol composition using the obtained high-purity aromatic methyl alcohol compound.

  本发明的目的是提供一种高纯度芳香族甲醇化合物，其中混有作为副产物的还原双(芳基甲基)醚化合物，以及一种具有优异保存稳定性的高纯度芳香族甲醇组合物及其生产方法。 本发明的目的是通过一种生产高纯度芳香族甲醇化合物的方法来实现的，该方法包括在有抗分解剂存在的情况下，通过对含芳香族甲醇的粗产品进行蒸馏，以高产率从该粗产品中获得高纯度芳香族甲醇化合物。此外，通过使用所获得的高纯度芳香族甲醇化合物生产高纯度芳香族甲醇组合物，还可实现防腐稳定性的目标。
• Bromophenols as Candida albicans isocitrate lyase inhibitors
  作者：Ki-Bong Oh、Heung Bae Jeon、Yu-Ri Han、Yeon-Ju Lee、Jiyoung Park、So-Hyoung Lee、Dongsik Yang、Mihyun Kwon、Jongheon Shin、Hyi-Seung Lee

  DOI：10.1016/j.bmcl.2010.09.015

  日期：2010.11

  A new series of bromophenols was synthesized by reactions of corresponding phenol analogs with bromine. The synthesized compounds were tested for inhibitory activity against isocitrate lyase (ICL) of Candida albicans and antimicrobial activity against Gram-positive and, Gram-negative bacteria and fungi. Among the synthesized bromophenols, bis(3-bromo-4,5-dihydroxyphenyl)methanone (11) and (3-bromo-4,5-dihydroxyphenyl)(2,3-dibromo-4,5-dihydroxyphenyl)methanone (12) displayed potent inhibitory activities against ICL, showing a stronger inhibitory effects than were found with natural bromophenol 1. The preliminary structure-activity relationships were investigated in order to determine the essential structural requirements for the inhibitory activities of these compounds against ICL of C. albicans. (C) 2010 Elsevier Ltd. All rights reserved.