bis[2-(hydroxymethyl)phenyl] selenide | 865855-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis[2-(hydroxymethyl)phenyl] selenide
• 英文别名: [2-[2-(Hydroxymethyl)phenyl]selanylphenyl]methanol
• CAS: 865855-26-1
• 化学式: C₁₄H₁₄O₂Se
• 分子量: 293.224
• InChiKey: RJMBTWCWZKNXKF-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  473.2±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  bis[2-(hydroxymethyl)phenyl] selenide 在 双氧水 作用下， 生成 1,1'-spirobi[3H-2,1-benzoxaselenole]
  参考文献：
  名称：

  取代基对作为谷胱甘肽过氧化物酶模拟物的芳香族环硒代酯和螺二氧基硒脲类的催化活性的影响

  摘要：

  在一系列芳族环状硒代酸酯和螺二氧基硒代脲酮中研究了取代基的作用，它们起着抗氧化剂硒代酶谷胱甘肽过氧化物酶模拟物的作用。甲氧基取代的亚硒酸酯被证明是最有效的用苄基硫醇还原过氧化氢的催化剂，并且通过给电子取代基提高了这两种反应速率。哈米特图分别表明亚硒酸盐和亚硒酸盐的ρ= -0.45和-3.1，这表明硒的氧化是其催化循环的速率决定步骤。

  DOI：

  10.1021/jo800381s
• 作为产物：
  描述：

  2,2'-硒基二苯甲酸 在 lithium aluminium tetrahydride 作用下， 以41 %的产率得到bis[2-(hydroxymethyl)phenyl] selenide
  参考文献：
  名称：

  含有二硫化物和硒化物基团的大环二聚体的意外形成和强大的抗氧化活性

  摘要：

  含有烷基或苄基双（硫代乙酰氧基）基团的硒化物的氧化和水解导致意外形成大环二聚体，每个大环二聚体包含两个硒化物和两个二硫键。这些化合物表现出有效的催化抗氧化活性。动力学实验表明涉及相应的硒氧化物和羟基过羟基硒脲烷中间体的自催化机制。

  DOI：

  10.1002/anie.202213744

文献信息

• <i>o</i>-Hydroxylmethylphenylchalcogens: Synthesis, Intramolecular Nonbonded Chalcogen···OH Interactions, and Glutathione Peroxidase-like Activity
  作者：Santosh K. Tripathi、Upali Patel、Dipankar Roy、Raghavan B. Sunoj、Harkesh B. Singh、Gotthelf Wolmershäuser、Ray J. Butcher

  DOI：10.1021/jo051309+

  日期：2005.11.1

  The synthesis and characterization of a series of organochalcogen (Se, Te) compounds derived from benzyl alcohol 13 are described. The synthesis of the key precursor dichalcogenides 15, 22, and 29 was achieved by the ortho-lithiation route. Selenide 18 was obtained by the reaction of the dilithiated derivative 14 with Se(dtc)2. Oxidation of 15 and 22 with H2O2 afforded the corresponding cyclic ester

  描述了一系列衍生自苄醇13的有机硫属元素（Se，Te）化合物的合成和表征。的关键前体二硫属化物的合成15，22，和29被实现邻-lithiation路线。通过二锂化衍生物14与Se（dtc）2的反应获得硒化物18。用H 2 O 2氧化15和22分别得到相应的环状酯衍生物17和24。硒化物的氧化18与H 2 O 2一起提供螺环化合物19。通过单晶X射线研究已经证明了二杀菌剂15和22中分子内相互作用的存在。环状化合物17和19也已经通过单晶X射线研究表征。已通过偶联生物测定法评估了GP X样硒化合物的抗氧化活性。双碲化物22在mPW1PW91级别的密度泛函理论计算已经确定了羟基氧和碲原子之间相当强的非键相互作用。通过NBO分析获得的二阶摄动能传达了n O →σ* Te - Te轨道重叠在非键相互作用中的参与。使用分子原子（AIM）方法进行波后功能分析，确定了15和22中不同的键临界点，并且还
• Enhanced Glutathione Peroxidase Activity of Water-Soluble and Polyethylene Glycol-Supported Selenides, Related Spirodioxyselenuranes, and Pincer Selenuranes
  作者：Nicole M. R. McNeil、David J. Press、Don M. Mayder、Pablo Garnica、Lisa M. Doyle、Thomas G. Back

  DOI：10.1021/acs.joc.6b01593

  日期：2016.9.2

  10 and 11, respectively, with greatly improved aqueous solubility and catalytic activity. The phenolic derivative 28 displayed similarly ameliorated properties and also modest radical-inhibiting antioxidant activity, as evidenced by an assay based on phenolic hydrogen atom transfer to the stable free radical DPPH. In contrast, several selenides that afford pincer selenuranes (e.g., 20 and 21) instead

  含有邻-羟基亚甲基取代基的二芳基硒化物通过抗氧化剂硒代酶谷胱甘肽过氧化物酶（GPx）的过氧化物破坏模拟物的作用，通过用过氧化氢氧化成相应的螺二氧基硒脲类，然后再用谷胱甘肽还原为原始硒化物。具有3-羟丙基或2，3-二羟丙基的母体硒化物分别产生了具有大大改善的水溶性和催化活性的新型化合物10和11。酚衍生物28通过基于酚氢原子转移到稳定的自由基DPPH的试验证明，其显示出相似的改善的性能以及适度的自由基抑制抗氧化剂活性。相比之下，几种硒化物可提供钳制的硒酮（例如20和21））代替螺旋藻类神经酰胺在氧化时显示出较差的催化活性。将几种硒化物类似物连接到聚乙二醇（PEG）低聚物上，因为PEG取代基可以改善水溶性和生物利用度，同时又会延迟清除率。再次，当氧化生成螺二氧基硒脲类时，PEG衍生物提供了显着的活性，并且当产生了夹子化合物时，PEG的活性降低了。几个这样的化合物被证明是大约。催化活性比先前研究
• WO2007/44641
  申请人：——

  公开号：——

  公开（公告）日：——
• Aromatic Derivatives and Tellurium Analogues of Cyclic Seleninate Esters and Spirodioxyselenuranes That Act as Glutathione Peroxidase Mimetics
  作者：Thomas G. Back、Dušan Kuzma、Masood Parvez

  DOI：10.1021/jo0512711

  日期：2005.11.1

  Several novel organoselenium and tellurium compounds were prepared and evaluated as mimetics of the selenoenzyme glutathione peroxidase, which protects cells from oxidative stress by reducing harmful peroxides with the thiol glutathione. The compounds were tested for catalytic activity in a model system wherein tert-butyl hydroperoxide or hydrogen peroxide were reduced with benzyl thiol and the rate of the reaction was measured by monitoring the formation of dibenzyl disulfide. Thus, aromatic derivatives 19, 22, 24, and 25 proved to be inferior catalysts compared to the parent cyclic seleninate ester 14 and spirodioxyselenurane 16. In the case of 19 and 22, this was the result of their rapid conversion to the relatively inert selenenyl sulfides 31 and 32, respectively. In general, hydrogen peroxide was reduced faster than tert-butyl hydroperoxide in the presence of the selenium-based catalysts. The cyclic tellurinate ester 27 and spirodioxytellurane 29 proved to be superior catalysts to their selenium analogues 14 and 16, respectively, resulting in the fastest reaction rates by far of all of the compounds we have investigated to date. Oxidation of 29 with hydrogen peroxide produced the unusual and unexpected peroxide 33, in which two hypervalent octahedral tellurium moieties are joined by ether and peroxide bridges. The structure of 33 was confirmed by X-ray crystallography. Although 33 displayed strong catalytic activity when tested independently in the model system, its relatively slow formation from the oxidation of 29 rules out its intermediacy in the catalytic cycle of 29.
• GPx-Like Activity of Selenides and Selenoxides: Experimental Evidence for the Involvement of Hydroxy Perhydroxy Selenane as the Active Species
  作者：Vanessa Nascimento、Eduardo E. Alberto、Daniel W. Tondo、Daniel Dambrowski、Michael R. Detty、Faruk Nome、Antonio L. Braga

  DOI：10.1021/ja209570y

  日期：2012.1.11

  The reaction mechanism of the GPx-like oxidation of PhSH with H2O2 catalyzed by selenoxides proceeds via formation of the hydroxy perhydroxy selenane, which is a stronger oxidizing agent than selenoxide. A hydroxy perhydroxy selenane intermediate was observed by electrospray ionization mass spectrometry and Se-77 NMR spectroscopy in reactions of selenoxide 8 with H2O2. The initial velocity of oxidation of PhSH by H2O2 with selenoxide 8 is 4 orders of magnitude higher than that of 8 without peroxide. Selenoxide 8 is not reduced to selenide 6 by PhSH in the presence of H2O2. While electronic substituent effects have minimal impact on the catalytic performance of selenoxides, chelating groups increase the rate of catalysis.