1,2,3,3-tetramethyl-3H-indolium perchlorate | 13330-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,2,3,3-tetramethyl-3H-indolium perchlorate
• 英文别名: 1,2,3,3-tetramethylindolenium perchlorate；1,2,3,3-tetramethylindolenylium perchlorate；1,2,3,3-tetramethylindolinium perchlorate；1,2,3,3-tetramethyl-3H-indol-1-ium perchlorate；1,2,3,3-tetramethylindoleninium perchlorate；3H-Indolium, 1,2,3,3-tetramethyl-, perchlorate；1,2,3,3-tetramethylindol-1-ium;perchlorate
• CAS: 13330-41-1
• 化学式: C₁₂H₁₆N*ClO₄
• 分子量: 273.716
• InChiKey: DRTPFKMRZXCGKX-UHFFFAOYSA-M

物化性质

• 熔点：
  198 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.04
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1,2,3,3-tetramethyl-3H-indolium perchlorate 在 吡啶 乙酸酐 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.16h， 生成 1-methyl-2,6-diphenyl-4-<5-(1,3,3-trimethyl-2-indolinylidene)penta-1,3-dien-1-yl>pyridinium perchlorate
  参考文献：
  名称：

  Pyrylocyanines. 12. Unsymmetrical pyrylo-2-cyanines

  摘要：

  DOI：

  10.1007/bf00557738
• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基吲哚啉 在 高氯酸 作用下， 以 乙醇 为溶剂， 生成 1,2,3,3-tetramethyl-3H-indolium perchlorate
  参考文献：
  名称：

  Reichardt, Christian; Budnik, Ulrich, Chemische Berichte, 1990, vol. 123, # 10, p. 2023 - 2030

  摘要：

  DOI：

文献信息

• 3<i>H</i>-indolium salts efficiently prepared from<i>N</i>-substituted anilines and α-branched ketones by an one-pot synthesis
  作者：Thomas Zimmermann、Ortwin Brede

  DOI：10.1002/jhet.5570410117

  日期：2004.1

  and the α-branched ketones 3 the 3H-indolium salts 1 and their fused derivatives 13 are prepared by combining a sodium nitrite nitrosation, a zinc dust reduction, a hydrazone formation and a Fischer indolization to a reaction sequence in which the isolation and purification of intermediates is not necessary. The scope and limitations of this effective one-pot synthesis are discussed.

  从N-取代的苯胺4/12和α-支化的酮3开始，通过结合亚硝酸钠亚硝化，还原锌粉尘，a的形成和Fischer吲哚化反应制得3 H-吲哚鎓盐1及其稠合衍生物13。不需要中间体的分离和纯化的反应顺序。讨论了这种有效的一锅法合成的范围和局限性。
• A facile synthesis of 3<i>H</i>-indolium perchlorates by one-pot hydrazone formation/fischer indolization
  作者：Thomas Zimmermann

  DOI：10.1002/jhet.5570370626

  日期：2000.11

  α-branched ketones 2 and perchloric acid react in boiling ethanol to give via the in situ formed hydrazones 3 1,2,3,3-tetrasubstituted 3H-indolium perchlorates 4. The scope and limitations of this facile synthesis of 3H-indolium derivatives which combines the hydrazone formation and the Fischer indolization to an one-pot procedure are discussed.

  ñ -取代Ñ -phenylhydrazines 1，α-支链酮2和高氯酸在沸腾的乙醇，得到的反应通过在原位形成腙3 1,2,3,3-四取代的3 ħ -indolium高氯酸盐4的范围和限制讨论了3 H-吲哚鎓衍生物的简便合成方法，该方法将the的形成和Fischer吲哚化结合为一锅法。
• Photochromic properties of cationic merocyanine dyes. Thermal stability of the spiropyran form produced by irradiation with visible light
  作者：Shigeyuki Yagi、Katsumi Maeda、Hiroyuki Nakazumi

  DOI：10.1039/a905098a

  日期：——

  A series of novel cationic merocyanine dyes were prepared by condensation of 1,2,3,3-tetramethylindolium derivatives and 3-formyl-4H-1-benzothiopyran or -benzopyran derivatives, and their photochromic properties were investigated, especially focusing on the substituent effect in the indolium moiety. These dyes were converted into the spiropyran (SP) form so as to be colorless by irradiation with visible light, although, left under darkness, the colored merocyanine (MC) form was reproduced. The thermal coloration was affected by two factors: the substituent in the indolium moiety and the counter anion. An electron-donating substituent such as a methoxy group at the 5 position effectively retarded the thermal coloration, whereas an electron-withdrawing group such as a nitro group accelerated it. These substituent effects afforded good linearity for the Hammett rule with para σ parameters, indicating that decrease of the electron density in the indoline moiety of the SP form facilitated heterolytic cleavage of the bond between the spiro carbon and the oxygen of the pyran ring.

  通过缩合反应制备了一系列新型阳离子型部花青染料，该反应涉及1,2,3,3-四甲基吲哚鎓衍生物与3-醛基-4H-1-苯并噻吡喃或苯并吡喃衍生物的反应，并研究了它们的光致变色性质，特别关注吲哚鎓部分中的取代基效应。这些染料在可见光照射下转化为无色的螺吡喃（SP）形式，尽管在黑暗环境中，带色的部花青（MC）形式会再次出现。热致变色受到两个因素的影响：吲哚鎓部分的取代基和反荷离子。在5位带有供电子取代基（如甲氧基）有效地延缓了热致变色，而吸电子基团（如硝基）则加速了热致变色。这些取代基效应提供了良好的Hammett规则线性关系，对应于para σ参数，表明在SP形式中吲哚部分电子密度降低促进了螺碳与吡喃环氧之间键的异裂解离。
• Synthesis and structure of indoline spiropyrans based on benzo[f]coumarin
  作者：O. G. Nikolaeva、O. Yu. Karlutova、A. A. Guseva、E. B. Gaeva、A. G. Starikov、A. D. Dubonosov、V. A. Bren、A. V. Metelitsa、V. I. Minkin

  DOI：10.1007/s11172-020-2912-6

  日期：2020.7

  Indoline spiropyrans containing benzo[f]coumarin moiety annulated to the 2H-pyran cycle were synthesized. The obtained compounds exist in solutions as a tautomeric mixture of their spirocyclic and merocyanine forms. The spiro form exhibits an enhanced resistance to UV irradiation and does not rearranges into the merocyanine isomer in the temperature range of 278–303 K.

  合成了含有与 2H-吡喃循环成环的苯并[f]香豆素部分的二氢吲哚螺吡喃。所得化合物以其螺环和部花青形式的互变异构混合物存在于溶液中。螺形式对紫外线照射具有增强的抵抗力，并且在 278-303 K 的温度范围内不会重新排列成部花青异构体。
• Synthesis and characterization of new derivatives of bis(1,4‐diazepinium) salts and bis(γ‐substituted pentamethine cyanine(dyes using vinamidinium salt
  作者：Fatemeh Habashi、Abdolmohammad Mehranpour、Enayatollah Bahman Jahromi

  DOI：10.1002/jhet.3958

  日期：2020.6

  The preparation of several bis(1,4‐diazepinium) salts from the reaction of three 1,2‐diamines with a bis(vinamidinium) salt is described. Bis(γ‐substituted pentamethine cyanine(dyes are also prepared from the reaction of vinamidinium salt with 1,2‐dimethylquinolinium perchlorate and 1,2,3,3‐tetramethyl‐3H‐indolium perchlorate. Data from elemental analyzes, IR, 1H‐NMR, 13C‐NMR, and mass spectra (MS)

  描述了由三种1,2-二胺与双（钒酰胺）盐反应制得的几种双（1,4-二氮杂吡啶鎓）盐。双（γ-取代的五甲胺花青（染料也可以通过将钒胺盐与1,2-二甲基喹啉高氯酸盐和1,2,3,3-四甲基-3H-高氯酸吲哚反应）制得。数据来自元素分析，IR，1 H ‐NMR，13 C‐NMR和质谱（MS）证实了所得产品的分子结构。