2,4-diphenyl-5,6-dihydro-7,8-benzochromenylium perchlorate | 74863-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2,4-diphenyl-5,6-dihydro-7,8-benzochromenylium perchlorate
• 英文别名: 5,6-dihydro-2,4-diphenylnaphtho<1,2-b>pyrylium perchlorate；2,4-diphenyl-7,8-benzo-5,6-dihydrochromenylium perchlorate；5,6-dihydro-2,4-diphenylbenzo[h]chromenylium perchlorate；2,4-diphenyl-5,6-dihydro-7,8-benzo[h]chromenylium perchlorate；Naphtho[1,2-b]pyrylium, 5,6-dihydro-2,4-diphenyl-, perchlorate；2,4-diphenyl-5,6-dihydrobenzo[h]chromen-1-ium;perchlorate
• CAS: 74863-87-9
• 化学式: C₂₅H₁₉O*ClO₄
• 分子量: 434.876
• InChiKey: UKQHGISLOLACGG-UHFFFAOYSA-M

物化性质

• 熔点：
  294-295 °C(Solv: methanol (67-56-1))

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• 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：

  2,4-diphenyl-5,6-dihydro-7,8-benzochromenylium perchlorate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到2-(1,3-diphenyl-3-oxopropylidene)-1-tetralone
  参考文献：
  名称：

  Katritzky, Alan R.; Thind, Sukhpal S., Journal of the Chemical Society. Perkin transactions I, 1980, p. 865 - 868

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(3-氧代-1,3-二苯基丙基)-3,4-二氢-2H-萘-1-酮 在 高氯酸 作用下， 生成 2,4-diphenyl-5,6-dihydro-7,8-benzochromenylium perchlorate
  参考文献：
  名称：

  Electronic absorption spectra of pyrylium and benzodihydrochromenylium salts

  摘要：

  The electronic absorption spectra of benzodihydrochromenylium, tetrahydrochromenylium, and dichloropyrylium salts were studied for the first time. It was noticed that intramolecular charge transfer takes place mainly between the substituent at position 4 of the pyrylium ring and the pi-system of the cation as a whole, while the bathochromic shift depends substantially on the geometry of the molecule. It was shown that the chlorine atoms have an effect on the form of the spectra when they are introduced into the ring of the pyrylium cation and into the aryl substituents.

  DOI：

  10.1007/s10593-008-0134-1

文献信息

• TEMPO-Attached Pre-fluorescent Probes Based on Pyridinium Fluorophores
  作者：Carolina Aliaga、Freddy Celis、Susan Lühr、Rubén Oñate

  DOI：10.1007/s10895-015-1579-0

  日期：2015.7

  The photophysical behavior of three pyridinium-derived fluorophores, the N-aryl-2,4,6-triphenylpyridinium, the N-aryl-5,6-dihydro-2,4-diphenylbenzo[h]quinolinium and the N-aryl-5,6,8,9-tetrahydro-7-phenyldibenzo[c,h]acridinium perchlorates, was investigated. Comparison of their fluorescence quantum yields led to the preparation of a novel, more sensitive pyridinium-based, TEMPO-attached prefluorescent probe for H-abstraction processes, the N-4-[4-(N-oxyl-2,2,6,6-tetramethylpiperidinyl)carbonylamino]phenyl}-5,6,8,9-tetrahydro-7-phenyldibenzo[c,h]-acridinium perchlorate.

  研究了三种吡啶盐类荧光染料的光物理行为，分别是N-芳基-2,4,6-三苯基吡啶盐、N-芳基-5,6-二氢-2,4-二苯基苯并[h]喹啉盐以及N-芳基-5,6,8,9-四氢-7-苯基二苯并[c,h]吖啶高氯酸盐。通过比较它们的荧光量子产率，制备了一种新型的、更灵敏的基于吡啶盐的TEMPO（2,2,6,6-四甲基哌啶-1-氧自由基）连接的前荧光探针，用于H-抽提过程，即N-4-[4-(N-氧基-2,2,6,6-四甲基哌啶基)羰基氨基]苯基}-5,6,8,9-四氢-7-苯基二苯并[c,h]吖啶高氯酸盐。
• Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. Part 10. Reactions of s-alkyl primary amines with pyryliums
  作者：Alan R. Katritzky、Jorge Marquet、Jeremy M. Lloyd、James G. Keay

  DOI：10.1039/p29830001435

  日期：——

  α-phenylbenzylamine forms the corresponding carbonium ions which may be trapped by nucleophiles. Isolated 1-cycloalkylbenzoquinoliniums (2) solvolyse but the SN1 mechanism (for five-, six-, and seven-membered rings): for the cyclobutyl case an SN2 reaction is also found.

  2,4,6-三苯基吡啶与仲烷基胺可制得可分离的吡啶鎓（吡啶鎓被亲核试剂取代为S N 2并消除为烯烃）。与1-苯基乙胺和α-苯基苄基胺形成的2,4,6-三苯基吡啶鎓形成相应的碳离子，这些碳离子可能被亲核试剂捕获。分离的1-环烷基苯并喹啉鎓盐（2）溶剂分解但具有S N 1机理（对于五元，六元和七元环）：对于环丁基，还会发现S N 2反应。
• Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. Part 9. N-substituted 2,4,6-triphenylpyridiniums, 5,6-dihydro-2,4-diphenylbenzo[h]quinoliniums, and 5,6,8,9-tetrahydro-7-phenyldibenzo[c,h]acridiniums: kinetic rate variation with structure of the N-substituent
  作者：Alan R. Katritzky、Kumars Sakizadeh、Yu Xiang Ou、Bratislav Jovanovic、Giuseppe Musumarra、Francesco P. Ballistreri、Roberto Crupi

  DOI：10.1039/p29830001427

  日期：——

  order benzyl > methyl ≃ s-alkyl > continuous chain primary alkyl ≃ neopentyl. Comparisons with literature data involving other leaving groups, standardized by reference to the ethyl compound in each series, again show that groups larger than ethyl tend to react faster in series (1), (2), and especially (3) than expected, and methyl tends to react more slowly. Similar but smaller trends are found in literature

  Ñ -N-烷基，Ñ -S-烷基，Ñ -烯丙基，和Ñ标题化合物的苄基衍生物与哌啶和其它亲核试剂反应，在清楚地可分离小号Ñ 1和/或小号ñ 2个反应。对于Ñ -s-三烷基化合物，小号Ñ 2率降低与亲核试剂亲核的，而小号Ñ 1速率是由亲核试剂的性质的影响。该小号Ñ 1反应显示出比找到符合更高的激活熵小号Ñ 2反应。尽管对于相同的N-取代基，SN 2比率始终以（1）<（2）<（3）的顺序增加，比率增强对于不同的N-取代基有很大变化：这些变化可以通过N-取代基的空间形状部分地合理化。通常，随着N-取代基尺寸的增加，增强作用也随之增加。对于小号Ñ在2个反应中，速率按苄基>甲基≃s-烷基>连续链伯烷基≃新戊基的顺序降低。与涉及其他离去基团的文献数据进行比较后，通过参考每个系列中的乙基化合物进行标准化，这再次表明，大于乙基的基团在系列（1），（2），尤其是（3）中的反应往往比预期的要快，并且甲基倾向于反应
• Katritzky, Alan R.; Singh, Jagadish N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 5, p. 421 - 424
  作者：Katritzky, Alan R.、Singh, Jagadish N.

  DOI：——

  日期：——
• Katritzky, Alan R.; Thind, Sukhpal S., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1895 - 1900
  作者：Katritzky, Alan R.、Thind, Sukhpal S.

  DOI：——

  日期：——