7-cyano-2,3-diphenylindolizin-1-yl triflate | 180601-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-cyano-2,3-diphenylindolizin-1-yl triflate
• 英文别名: 1-(Trifluoromethylsulfonyloxy)-2,3-diphenylindolizine-7-carbonitrile；(7-cyano-2,3-diphenylindolizin-1-yl) trifluoromethanesulfonate
• CAS: 180601-86-9
• 化学式: C₂₂H₁₃F₃N₂O₃S
• 分子量: 442.418
• InChiKey: ISUQMUJWDCSSRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-cyano-2,3-diphenylindolizin-1-yl triflate 在 tetramethylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以55%的产率得到7-cyano-1,7-dihydro-2,3-diphenyl-1-oxoindolizinium tetrafluoroborate
  参考文献：
  名称：

  Electrochemical studies of biologically active indolizines

  摘要：

  The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E degrees values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E degrees values have been correlated with the Hammett substituent parameters. As expected, low E degrees values are seen for electron donating substituents and higher E degrees values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the CA position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E degrees values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the G I position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1' dimers of indolizines as products in good yields. Bulk oxidation of 1-(alpha-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitfile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-I position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.078
• 作为产物：
  描述：

  二苯基环丙烯酮 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 7-cyano-2,3-diphenylindolizin-1-yl triflate
  参考文献：
  名称：

  1-取代 7-氰基-2,3-二苯基吲哚腙的合成及抗氧化性能评价

  摘要：

  已经开发了用于从相应的吲哚啉醇合成新型 1-取代的 7-氰基-2,3-二苯基吲哚嗪的方案，并且已经检查了这些化合物作为抗氧化剂的能力，即抑制体外脂质过氧化。1-bromo-7-cyano-2,3-diphenylindolizine 9 很容易参与 pd 催化的与有机锡、有机锌和有机硼试剂的偶联反应。另一方面，对相应的吲哚嗪基三氟甲磺酸酯 6 的类似处理仅导致三氟甲磺酸酯部分裂解回吲哚嗪醇，但与 1-乙氧基乙烯基（三丁基）锡反应除外。在这里，形成了意想不到的乙缩醛（1-乙氧基乙氧基）茚10。10 的结构是通过单晶 X 射线衍射方法在 150 k 处确定的。在 c-1 处引入取代基的另一种策略是将溴化物 9 锂化，然后与亲电子试剂反应。检测了吲哚嗪衍生物在体外抑制脂质过氧化的能力。煮熟的大鼠肝微粒体的脂质过氧化是由抗坏血酸/feso4 诱导的，过氧化是通过测量与硫代巴比妥酸反应的物质来确定的。特别是，吲哚嗪乙酸酯

  DOI：

  10.1002/1099-0690(200011)2000:22<3763::aid-ejoc3763>3.0.co;2-s

文献信息

• [EN] THE USE OF HETEROCYCLIC COMPOUNDS AS ANTIOXIDANTS, RADICAL SCAVENGERS, Fe<2+> COMPLEXING AGENTS, TISSUE- AND/OR NEUROPROTECTANTS<br/>[FR] UTILISATION DE COMPOSES HETEROCYCLIQUES COMME ANTIOXYDANTS, PIEGEURS DE RADICAUX, AGENTS DE COMPLEXATION DE FE<2+>, PROTECTEURS TISSULAIRES ET/OU NEUROPROTECTEURS
  申请人：RISE, Frode

  公开号：WO1996021662A1

  公开（公告）日：1996-07-18

  (EN) The invention relates to the new use of compounds of formula (I), wherein X is a member selected from the group consisting of O, S, Se, Te, SO, SO2, SeO, SeO2, TeO, TeO2; for the manufacture of a pharmaceutical composition having the effect of an antioxidant, radical scavenger, Fe2+ complexing agent, tissue- and/or neuroprotectant. The invention also relates to new compounds falling within Formula (I) and pharmaceutical compositions containing them as well as a method for the prevention or treatment of diseases causes by oxidative stress.(FR) L'invention concerne la nouvelle utilisation de composés de formule (I), dans laquelle X représente un élément choisi dans le groupe constitué de O, S, Se, Te, SO, SO2, SeO, SeO2, TeO, TeO2; cette nouvelle utilisation est destinée à la fabrication d'une composition pharmaceutique ayant l'effet d'un antioxydant, d'un piégeur de radicaux, d'un agent de complexation de Fe2+, et de protecteur tissulaire et/ou de neuroprotecteur. L'invention porte également sur des nouveaux composés englobés par la formule (I) et des compositions pharmaceutiques les contenant, ainsi qu'une méthode de prévention ou de traitement de maladies induites par le stress oxydatif.
• Synthesis of 1-Substituted 7-Cyano-2,3-diphenylindolizines and Evaluation of Antioxidant Properties
  作者：Ole Benny Østby、Bjørn Dalhus、Lise-Lotte Gundersen、Frode Rise、Aalt Bast、Guido R. M. M. Haenen

  DOI：10.1002/1099-0690(200011)2000:22<3763::aid-ejoc3763>3.0.co;2-s

  日期：2000.11

  Protocols for the synthesis of novel 1-substituted 7-cyano-2,3-diphenylindolizines from the corresponding indolizinol have been developed, and the compounds’ abilities to act as antioxidants, i.e. To inhibit lipid peroxidation in vitro, have been examined. 1-bromo-7-cyano-2,3-diphenylindolizine 9 readily participates in pd-catalysed coupling reactions with organotin, organozinc, and organoboron reagents. Similar

  已经开发了用于从相应的吲哚啉醇合成新型 1-取代的 7-氰基-2,3-二苯基吲哚嗪的方案，并且已经检查了这些化合物作为抗氧化剂的能力，即抑制体外脂质过氧化。1-bromo-7-cyano-2,3-diphenylindolizine 9 很容易参与 pd 催化的与有机锡、有机锌和有机硼试剂的偶联反应。另一方面，对相应的吲哚嗪基三氟甲磺酸酯 6 的类似处理仅导致三氟甲磺酸酯部分裂解回吲哚嗪醇，但与 1-乙氧基乙烯基（三丁基）锡反应除外。在这里，形成了意想不到的乙缩醛（1-乙氧基乙氧基）茚10。10 的结构是通过单晶 X 射线衍射方法在 150 k 处确定的。在 c-1 处引入取代基的另一种策略是将溴化物 9 锂化，然后与亲电子试剂反应。检测了吲哚嗪衍生物在体外抑制脂质过氧化的能力。煮熟的大鼠肝微粒体的脂质过氧化是由抗坏血酸/feso4 诱导的，过氧化是通过测量与硫代巴比妥酸反应的物质来确定的。特别是，吲哚嗪乙酸酯
• Electrochemical studies of biologically active indolizines
  作者：Solomon Teklu、Lise-Lotte Gundersen、Frode Rise、Mats Tilset

  DOI：10.1016/j.tet.2005.02.078

  日期：2005.5

  The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E degrees values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E degrees values have been correlated with the Hammett substituent parameters. As expected, low E degrees values are seen for electron donating substituents and higher E degrees values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the CA position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E degrees values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the G I position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1' dimers of indolizines as products in good yields. Bulk oxidation of 1-(alpha-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitfile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-I position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism. (c) 2005 Elsevier Ltd. All rights reserved.