9-(3-Methylphenyl)xanthen-9-ol | 29903-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-(3-Methylphenyl)xanthen-9-ol
• 英文别名: 9-m-tolyl-xanthen-9-ol；9-(3-methylphenyl)-9H-xanthen-9-ol；9-(3'-Methylphenyl)-xanthenol
• CAS: 29903-56-8
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: WWASCZKPZDLCDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(3-Methylphenyl)xanthen-9-ol 在 tetrafluoroboric acid 作用下， 以 丙酸酐 为溶剂， 以43%的产率得到9-(3-Methylphenyl)xanthylium tetrafluoroborate
  参考文献：
  名称：

  Quenching behavior of singlet excited 9-arylxanthylium cations

  摘要：

  Several 9-arylxanthylium tetrafluoroborate salts (Ar = H, p,m-F, p,m-Me, m-OMe) were synthesized by reaction of the corresponding 9-arylxanthen-9-ol with fluoroboric acid. Spectral characteristics of the xanthyl cations were identical to those previously reported for the cations generated by alternate methods. The 9-arylxanthyl cation fluorescence was quenched by the addition of H2O, MeOH, i-PrOH, and t-BuOH. Stern-Volmer analysis of the fluorescence quenching gave bimolecular excited-state rate constants ranging from 10(6) to 10(10) M-1 s-1, with the larger rate constants associated with electron-donating substituents. Hammett plots of log[k(q)(X)/k(q)(H)] versus sigma(hnu) gave negative p values for each quencher, opposite to the substituent dependence observed for ground-state cations reacting with nucleophiles. The relative quenching order also differs from the order observed for ground-state cation reactions. The mechanism for quenching of the singlet excited 9-arylxanthylium cations is evaluated in terms of nucleophilic attack. The possibility of an electron-transfer mechanism is considered and eliminated.

  DOI：

  10.1021/jo00073a050
• 作为产物：
  描述：

  占吨酮 、 M-TOLYLMAGNESIUM BROMIDE 以 乙醚 为溶剂， 反应 6.0h， 生成 9-(3-Methylphenyl)xanthen-9-ol
  参考文献：
  名称：

  Electrophilic reactions of xanthylium carbocations produced by flash photolysis of 9-xanthenols

  摘要：

  DOI：

  10.1021/ja00190a030

文献信息

• Tricylic amino-acid derivatives
  申请人：Allelix Neuroscience Inc.

  公开号：US06162824A1

  公开（公告）日：2000-12-19

  Described herein are compounds which have the general formula: ##STR1## or a prodrug or pharmaceutically acceptable salt, solvate or hydrate thereof wherein: R.sup.1 is selected from the group consisting of H, alkyl and the counter ion for a basic addition salt; X is selected from the group consisting of CR.sup.9 R.sup.10, S, O, SO, SO.sub.2, NH and N-alkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.9 and R.sup.10 are independently selected from the group consisting of H and alkyl; R.sup.5 and R.sup.6 are independently selected from the group consisting of H, alkyl and phenyl, or, alternatively, R.sup.5 and R.sup.6 together may form a methylene group or a 3- to 6-membered a spirocyclic group; wherein, when X is CR.sup.9 R.sup.10, one or both pairs of R.sup.5 and R.sup.9 or R.sup.6 and R.sup.10 may join to form a double or triple bond R.sup.7 is selected from the group consisting of Formula II-V: ##STR2## which are all optionally substituted, at nodes other than R.sup.8, with 1-4 substituents independently selected from the group consisting of alkyl, halo, aryl (which may be substituted as for R.sup.8), trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, mono-alkylamino, di-alkylamino, alkoxycarbonyl, alkylcarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl, alkoxy, alkylS-, phenoxy, --SO.sub.2 NH.sub.2, --SO.sub.2 NHalkyl, --SO.sub.2 N(alkyl).sub.2 and 1,2-methylenedioxy; and wherein any of the benzo-fused rings in structures II to V may be replaced by a 5- or 6-membered heterocyclic ring selected from the group consisting of pyridine, thiophene, furan and pyrrole; wherein R.sup.8 is selected from the group consisting of H, alkyl, benzyl, cycloalkyl, indanyl and an optionally substituted aryl group, wherein the optional substituents are independently selected from 1-4 members of the group consisting of alkyl, halo, aryl, trifluoromethyl, trifluoromethoxy, nitro, cyano, amino, mono-alkylamino, di-alkylamino, alkoxycarbonyl, alkylcarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl, alkoxy, alkylS-, phenoxy, --SO.sub.2 NH.sub.2, --SO.sub.2 NHalkyl, --SO.sub.2 N(alkyl).sub.2 and 1,2-methylenedioxy; --represents a single or double bond; Y is selected from the group consisting of O, S, SO, NH, N-alkyl, CH.sub.2, CH-alkyl, C(alkyl).sub.2, and C.dbd.O; Z is selected from the group consisting of CH.sub.2, O, S, NH and N-alkyl when--is a single bond; Z is selected from the group consisting of CH and N when--is a double bond. Also described is the use of these compounds as pharmaceuticals.

  本文描述了具有以下一般式的化合物：##STR1##或其前药或药用可接受的盐、溶剂或水合物，其中：R.sup.1选自H、烷基和碱性加成盐的对离子组成的群；X选自CR.sup.9 R.sup.10、S、O、SO、SO.sub.2、NH和N-烷基的群；R.sup.2、R.sup.3、R.sup.4、R.sup.9和R.sup.10独立地选自H和烷基的群；R.sup.5和R.sup.6独立地选自H、烷基和苯基，或者，作为另一选择，R.sup.5和R.sup.6可以一起形成亚甲基基团或3-至6-成员的螺环基团；当X为CR.sup.9 R.sup.10时，R.sup.5和R.sup.9或R.sup.6和R.sup.10中的一个或两个对可能连接以形成双键或三键R.sup.7选自以下式II-V的群：##STR2##它们都可以在除R.sup.8之外的节点上选择性地取代，取代基独立地选自烷基、卤素、芳基（可能像R.sup.8那样被取代）、三氟甲基、三氟甲氧基、硝基、氰基、氨基、单烷基氨基、双烷基氨基、烷氧羰基、烷基羰基、烷氧硫代羰基、烷基硫代羰基、烷氧基、烷基硫、苯氧基、--SO.sub.2 NH.sub.2、--SO.sub.2 NH烷基、--SO.sub.2 N(烷基).sub.2和1,2-亚甲二氧基；结构II至V中的苯并环中的任何一个都可以被选择自吡啶、噻吩、呋喃和吡咯的5-或6-成员杂环环取代；其中R.sup.8选自H、烷基、苄基、环烷基、茚基和一个可选择性取代的芳基，其中可选择性取代基独立地选自烷基、卤素、芳基、三氟甲基、三氟甲氧基、硝基、氰基、氨基、单烷基氨基、双烷基氨基、烷氧羰基、烷基羰基、烷氧硫代羰基、烷基硫代羰基、烷氧基、烷基硫、苯氧基、--SO.sub.2 NH.sub.2、--SO.sub.2 NH烷基、--SO.sub.2 N(烷基).sub.2和1,2-亚甲二氧基；--表示单键或双键；Y选自O、S、SO、NH、N-烷基、CH.sub.2、CH-烷基、C(烷基).sub.2和C.dbd.O的群；当--为单键时，Z选自CH.sub.2、O、S、NH和N-烷基的群；当--为双键时，Z选自CH和N的群。还描述了这些化合物作为药物的用途。
• Schoenberg; Mustafa, Journal of the Chemical Society, 1947, p. 997,1000
  作者：Schoenberg、Mustafa

  DOI：——

  日期：——
• US6162824A
  申请人：——

  公开号：US6162824A

  公开（公告）日：2000-12-19
• [EN] TRICYCLIC COMPOUNDS AS GLYCINE TRANSPORT INHIBITORS<br/>[FR] COMPOSES TRICYCLIQUES COMME INHIBITEURS DE TRANSPORT DE GLYCINE
  申请人：ALLELIX NEUROSCIENCE, INC.

  公开号：WO1999041227A1

  公开（公告）日：1999-08-19

  (EN) The present invention relates to a class of substituted amino acids, pharmaceutical compositions and methods of treating neurological and neuropsychiatric disorders.(FR) L'invention concerne une classe d'acides aminés substitués, des compositions pharmaceutiques et des procédés permettant de traiter des troubles neurologiques et neuropsychiatriques.
• Electrophilic reactions of xanthylium carbocations produced by flash photolysis of 9-xanthenols
  作者：Robert A. McClelland、Narinder Banait、Steen Steenken

  DOI：10.1021/ja00190a030

  日期：1989.4