4-phenyl-2,6-di-p-tolyl-pyrylium; perchlorate

• 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: 4-phenyl-2,6-di-p-tolyl-pyrylium; perchlorate
• 英文别名: 4-Phenyl-2,6-di-p-tolyl-pyrylium; Perchlorat；2,6-Bis(4-methylphenyl)-4-phenylpyrylium;perchlorate
• 化学式: C₂₅H₂₁O*ClO₄
• 分子量: 436.892
• InChiKey: IOGDELCZFMLKHD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-phenyl-2,6-di-p-tolyl-pyrylium; perchlorate 在 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.0h， 生成 {4-Methyl-5'-[1-methyl-1-(2-phenylamino-phenyl)-ethyl]-[1,1';3',1'']terphenyl-4'-yl}-p-tolyl-methanone
  参考文献：
  名称：

  Ringtransformationen heterocyclischer Verbindungen. XII. Neuartige Spiroindoline via Ringtransformation von 2,4,6-Triaryl-pyryliumsalzen mit 2-Methylen-indolinen

  摘要：

  2,4,6-Triarylpyrylium salts 1 react with 2-methyleneindolines 2 or their salts 2 HX in the presence of triethylamine/acetic acid in ethanol by a 2,5-[C-4 + C-2] pyrylium ring transformation to give diastereomerically pure 6-aroyl-3,5-diaryl-spiro[cyclohexa-2,4-diene-1,2'-indolines] 3, which represent a novel type of spiroindoline compounds. When the 1'-phenyl substituted spiroindolines 3 (R=Ph, R'=H) are treated with p-toluenesulfonic acid in chloroform the 4,6-diaryl-2- [1-methyl-1- (2-phenylaminophenyl) methyl]benzophenones 4 are obtained as the result of an intramolecular amine elimination. Structural elucidation of the reaction products 3/4 is based on spectroscopic data and on an X-ray determination of the bis(4-bromophenyl) substituted spiroindoline 3i.

  DOI：

  10.1002/prac.19953370179
• 作为产物：
  描述：

  3-phenyl-1,5-di-p-tolylpenta-1,4-diyn-3-ol 在 高氯酸 、 水 作用下， 以 乙醇 、 苯 为溶剂， 以79%的产率得到4-phenyl-2,6-di-p-tolyl-pyrylium; perchlorate
  参考文献：
  名称：

  用HClO 4由三取代的1,4-戊二炔-3-醇合成吡喃鎓盐

  摘要：

  首次报道了由1,3,5-三取代的1,4-戊二炔-3-醇与HClO 4合成2,4,6-三取代的吡啶鎓盐。

  DOI：

  10.1016/s0040-4039(01)81547-1

文献信息

• Ring transformations of heterocyclic compounds.<b>XXII</b>. Pyrido[1,2-<i>a</i>]indolium salts from 2-methyl-3<i>H</i>-indoles by pyrylium mediated three carbon annelation
  作者：Thomas Zimmermann、Lothar Hennig

  DOI：10.1002/jhet.5570390203

  日期：2002.3

  The synthesis of pyrido[1,2-a]indolium perchlorates 8,11 from 2,4,6-triarylpyrylium perchlorates 1 and 2-methyl-3H-indoles 6,9 in the presence of a basic condensing agent (anhydrous sodium acetate, piperidine acetate, triethylamine/acetic acid, triethylamine) in ethanol by a 2,4-[C3+C2N] pyrylium ring transformation is reported. Spectroscopic data of the transformation products and their mode of formation

  吡啶并合成[1,2一]吲哚鎓高氯酸盐-8,11-从2,4,6-三芳基高氯酸盐1和2-甲基-3- ħ -indoles 6,9在碱性缩合剂的存在下（无水醋酸钠报道了乙醇中乙酸哌啶，三乙胺/乙酸，三乙胺通过2，4- [C 3 + C 2 N]吡啶鎓环的转化。讨论了转化产物的光谱数据及其形成方式。
• Ring transformations of heterocyclic compounds.<b>XXI</b>. Diastereoselective built-up of an aroylcyclohexadiene moiety as second spiro-connected ring at spiroindolines by pyrylium ring transformation
  作者：Thomas Zimmermann

  DOI：10.1002/jhet.5570390202

  日期：2002.3

  cycloalkene or a heterocyclic system. These diastereoselective 2,5-[C4+C2] pyrylium ring transformations are carried out in the presence of triethylamine/acetic acid in boiling ethanol to give the dispiroindolines 4 with a trans configuration of the more bulky substituents at the cyclohexadiene ring. By the same type of transformation the dispiro compounds 7/10 with an additional fused benzene ring are obtained

  2,4,6-三芳基吡啶鎓高氯酸盐1与由相应的甲基吲哚盐2原位生成的亚甲基二氢吲哚3 反应，该亚甲基二氢吲哚盐3与环烷烃，苯甲酰化环烯烃或杂环系统螺旋稠合。这些非对映选择性的2，5- [C 4 + C 2 ]吡喃鎓环转化是在三乙胺/乙酸的存在下于沸腾的乙醇中进行的，以得到在环己二烯环上具有更大体积取代基的反式构型的二螺二吲哚啉4。通过相同类型的转化，双螺化合物7/10从吡喃鎓盐1a和6/9（苯并稠合的3的类似物）获得带有额外的稠合苯环的苯并稠合类似物。讨论了转化产物的光谱数据及其形成方式。
• Ring transformations of heterocyclic compounds.<b>XVI</b>. Spiro[cyclohexadiene-dihydroacridines]. A novel class of spirodihydroacridines by ring transformation of pyrylium salts with 9-methylacridine and its quaternary salts
  作者：Thomas Zimmermann、Ulrich Abram、Klaus Schmidt

  DOI：10.1002/jhet.5570350403

  日期：1998.7

  e] 4a is formed. The same compounds 4 can also be obtained by transformation of the pyrylium salts 1 with 9-methylacridine (7) and triefhylamine/acetic acid in ethanol. Structure elucidation is performed by an X-ray crystal structure determination of the spiro[cyclohexadiene-dihydroacridine] 3a. Spectroscopic data of the transformation products and their mode of formation are discussed.

  2,4,6-三芳基吡啶鎓盐1在乙醇中存在无水乙酸钠的情况下，通过2,5- [C 4 + C 2 ]吡啶环与原位生成的9,10-二甲基ac基硫酸甲酯（2a）的脱水碱反应转化得到迄今未知的6-芳酰基-3,5-二芳基-10'-甲基螺[环己-2,4-二烯-1,9'-9'，10'-二氢-啶] 3。当高氯酸吡啶鎓盐1a在相同条件下用N-乙基，N-烯丙基或N-苄基取代的cri啶盐2b-d处理时，这些盐会发生脱烷基，并且N形成-未取代的螺[环己二烯-二氢ac啶] 4a。相同的化合物4也可以通过用9-甲基9啶（7）和三乙胺/乙酸在乙醇中转化吡喃鎓盐1而获得。通过对螺[环己二烯-二氢ac啶] 3a的X射线晶体结构测定来进行结构阐明。讨论了转化产物的光谱数据及其形成方式。
• Ring transformations of heterocyclic compounds. XVII, 2-(2,4,6-Triarylphenyl) substituted dihydro-1<i>H</i>-imidazolium, dihydrothiazolium and thiazolium salts from 2-methyl derivatives by pyrylium and thiopyrylium ring transformations
  作者：Thomas Zimmermann

  DOI：10.1002/jhet.5570360339

  日期：1999.5

  The synthesis of hitherto unknown 2-(2,4,6-triarylphenyl) substituted 4,5-dihydro-1H-imidazolium perchlorates 6, 4,5-dihydrothiazolium perchlorates 8 and thiazolium perchlorates 9 from their 2-methyl derivatives 2, 4 and 5, respectively, by a 2,6-[C5+C] ring transformation of 2,4,6-triarylpyrylium and -thiopyrylium salts 1/10 in ethanol in the presence of an appropriate base (6: sodium ethanolate;

  迄今未知的2-（2,4,6- triarylphenyl）的合成取代的4,5-二氢- 1 H ^ -咪唑高氯酸盐6，4,5- dihydrothiazolium高氯酸盐8和噻唑鎓高氯酸盐9从它们的2-甲基衍生物2，4和5分别是在适当的碱存在下，在乙醇中将2,4,6-三芳基吡啶鎓盐和-硫代吡啶鎓盐1/10进行2,6- [C 5 + C]环转化（6：乙醇钠；8 ，9：无水乙酸钠）的报道。改造产品和结构的影响对其形成的光谱数据通过盐的anhydrobases 2，4和5进行了讨论。
• Ring transformations of heterocyclic compounds.<b>XXV</b>. Phenanthrene aldehyde imines via ring transformation of pyrylium salts with methylenedihydroisoquinolines-A novel access to the phenanthrene skeleton
  作者：Thomas Zimmermann、Harald Krautscheid

  DOI：10.1002/jhet.5570440509

  日期：2007.9

  phenanthrene-9-carbaldehyde imines 4 are obtained, the structure of which was confirmed by an X-ray structure determination of the 1-(4-methylphenyl) substituted derivative. Acid catalyzed hydrolysis of the imines 4 gives rise to the parent phenanthrene aldehydes. The transformation 1 + 2(6) → 4 represents a novel access to the phenanthrene skeleton.

  据报道，在碱的存在下，由相关的2-甲基异喹啉鎓盐2原位产生的2,4,6-三芳基吡啶盐1与2-亚甲基二氢异喹啉6的环转化。甲醇中的1（2）（6）和甲醇钠的转化可生成2-（2,4,6-三芳基苯基）异喹啉鎓盐，乙醇中的乙醇钠可得到芳基取代的菲-9-甲醛亚胺4，通过1-（4-甲基苯基）取代的衍生物的X射线结构测定来确认其结构。酸催化的亚胺4水解生成母体菲醛。转换1 + 2（6）→ 4表示对菲骨架的新颖访问。