allyl 2-carboxyphenyl selenide | 865855-24-9

• 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: allyl 2-carboxyphenyl selenide
• 英文别名: 2-(allylselenyl)benzoic acid；2-Prop-2-enylselanylbenzoic acid
• CAS: 865855-24-9
• 化学式: C₁₀H₁₀O₂Se
• 分子量: 241.148
• InChiKey: FKXHOMSJQIIFDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allyl 2-carboxyphenyl selenide 在 叔丁基过氧化氢 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 2-Benzylsulfanylselanylbenzoic acid
  参考文献：
  名称：

  Aromatic Derivatives and Tellurium Analogues of Cyclic Seleninate Esters and Spirodioxyselenuranes That Act as Glutathione Peroxidase Mimetics

  摘要：

  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.

  DOI：

  10.1021/jo0512711
• 作为产物：
  描述：

  丙烯酰碘 、 双（2-羧基苯基）二硒化物 在 sodium tetrahydroborate 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.25h， 以67%的产率得到allyl 2-carboxyphenyl selenide
  参考文献：
  名称：

  WO2007/44641

  摘要：

  公开号：

文献信息

• Synthesis and anti-inflammatory activity evaluation of unsymmetrical selenides
  作者：Federico Martínez-Ramos、Hector Salgado-Zamora、Maria Elena Campos-Aldrete、Estela Melendez-Camargo、Yazmín Márquez-Flores、Manuel Soriano-García

  DOI：10.1016/j.ejmech.2007.09.029

  日期：2008.7

  2'-diseleno and 4,4'-diseleno-bis(benzoic acid) derivatives in the presence of sodium borohydride and alkyl halides allowed the synthesis of various new o- and p-alkylselenenylated benzoic acid derivatives in good yields. The anti-inflammatory activity of selected selenide derivatives on granuloma induced by subcutaneous implantation of cotton pellets in Wistar rats was examined. Selenium derivatives

  在硼氢化钠和烷基卤化物的存在下2,2'-二硒代和4,4'-二硒代双（苯甲酸）衍生物的烷基化反应可以合成许多新的邻-和对-烷基硒烯化苯甲酸衍生物产量。检测了选定的硒化物衍生物对Wistar大鼠皮下植入棉丸后诱导的肉芽肿的抗炎活性。硒衍生物2a，2c和2e具有消炎活性，尽管与消炎痛相比程度较小，但毒性却比后者低。
• 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.