bis[2-(hydroxymethyl)phenyl] diselenide | 141819-07-0

• 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] diselenide
• 英文别名: Ortho-hydroxymethylphenyl diselenide；[2-[[2-(hydroxymethyl)phenyl]diselanyl]phenyl]methanol
• CAS: 141819-07-0
• 化学式: C₁₄H₁₄O₂Se₂
• 分子量: 372.184
• InChiKey: GFVXRRDYLMJKHC-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C(Solv: toluene (108-88-3))
• 沸点：
  540.9±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  18
• 可旋转键数：
  5
• 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] diselenide 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以96%的产率得到1,2-bis(2-(bromomethyl)phenyl)diselenide
  参考文献：
  名称：

  重排原子对二价硒和卤素原子之间弱非键相互作用强度的影响

  摘要：

  2-硒代苄基卤化物衍生物的77Se NMR化学位移和密度泛函理论计算表明，二价硒与卤原子的分子内非键相互作用强度依次降低，Se…F>Se…Cl≥ Se···Br.

  DOI：

  10.1246/cl.2002.518
• 作为产物：
  描述：

  methyl 2-selenocyanatobenzoate 在 盐酸 、 lithium aluminium tetrahydride 、 air 作用下， 生成 bis[2-(hydroxymethyl)phenyl] diselenide
  参考文献：
  名称：

  Iwaoka, Michio; Tomoda, Shuji, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 67, # 1-4, p. 125 - 130

  摘要：

  DOI：

文献信息

• Substituent Effects upon the Catalytic Activity of Aromatic Cyclic Seleninate Esters and Spirodioxyselenuranes That Act as Glutathione Peroxidase Mimetics
  作者：David J. Press、Eric A. Mercier、Dušan Kuzma、Thomas G. Back

  DOI：10.1021/jo800381s

  日期：2008.6.1

  Substituent effects were studied in a series of aromatic cyclic seleninate esters and spirodioxyselenuranes that function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. The methoxy-substituted selenurane proved the most efficacious catalyst for the reduction of hydrogen peroxide with benzyl thiol, and the reaction rates were enhanced for both classes by electron-donating substituents

  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。
• <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
• Diselenides and Benzisoselenazolones as Antiproliferative Agents and Glutathione-S-Transferase Inhibitors
  作者：Dorota Krasowska、Nunzio Iraci、Claudio Santi、Józef Drabowicz、Marcin Cieslak、Julia Kaźmierczak-Barańska、Martina Palomba、Karolina Królewska-Golińska、Jakub Magiera、Luca Sancineto

  DOI：10.3390/molecules24162914

  日期：——

  A series of variously functionalized selenium-containing compounds were purposely synthesized and evaluated against a panel of cancer cell lines. Most of the compounds showed an interesting cytotoxicity profile with compound 5 showing a potent activity on MCF7 cells. The ethyl amino derivative 5 acts synergistically with cis-platin and inhibits the GST enzyme with a potency that well correlates with the cytotoxicity observed in MCF7 cells. A computational analysis suggests a possible binding mode on the GST enzyme. As the main outcome of the present study, the ethyl amino derivative 5 emerged as a valid lead compound for further, future developments.

  一系列功能化的含硒化合物被有意合成并针对一系列癌细胞系进行评估。大多数化合物展现出有趣的细胞毒性谱，其中化合物5在MCF7细胞中表现出强效活性。乙基氨基衍生物5与顺铂呈协同作用，并抑制了GST酶的活性，其活性与在MCF7细胞中观察到的细胞毒性密切相关。计算分析表明，乙基氨基衍生物5可能在GST酶上存在结合模式。作为本研究的主要结果，乙基氨基衍生物5被确定为一个有效的引物化合物，可用于进一步未来的开发。
• 2-Phenoxyethanol derived diselenide and related compounds; synthesis of a seven-membered seleninate ester
  作者：Santosh K. Tripathi、Sagar Sharma、Harkesh B. Singh、Ray J. Butcher

  DOI：10.1039/c0ob00038h

  日期：——

  Syntheses of several diorganodiselenides and, in particular, a seven-membered cyclic seleninate ester derived from 2-phenoxyethanol are described. The seleninate ester was obtained from allyl (2-(2-hydroxyethoxy)phenyl) selenide through a series of oxidation and [2,3] sigmatropic rearrangement steps. The ester exhibits good GPx-like activity in the coupled reductase assay.

  几种二有机二硒化物的合成，尤其是由 2-苯氧基乙醇被描述。硒酸酯从烯丙基（2-（2-羟基乙氧基）苯基）硒化物通过一系列的氧化和[2,3]σ重排步骤。该酯在偶联还原酶测定法中表现出良好的GPx样活性。
• Heavy-Row Atom Effects on the Strength of the Weak Nonbonded Interactions between Divalent Selenium and Halogen Atoms
  作者：Michio Iwaoka、Takayuki Katsuda、Shuji Tomoda、Jun Harada、Keiichiro Ogawa

  DOI：10.1246/cl.2002.518

  日期：2002.5

  The 77Se NMR chemical shifts observed for 2-selenobenzyl halide derivatives and the density functional theoretical calculation revealed that the strength of intramolecular nonbonded interactions between a divalent selenium and halogen atoms decreases in the order, Se···F>Se···Cl≥Se···Br.

  2-硒代苄基卤化物衍生物的77Se NMR化学位移和密度泛函理论计算表明，二价硒与卤原子的分子内非键相互作用强度依次降低，Se…F>Se…Cl≥ Se···Br.