4-[2-(4-methoxyphenyl)ethenyl]-N-methylpyridinium iodide | 95495-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-(4-methoxyphenyl)ethenyl]-N-methylpyridinium iodide
• 英文别名: trans-1-methyl-4-methoxy-stilbazolium iodide；(E)-4-[4-(methoxy)styryl]-1-methylpyridinium iodide；(E)-4-[2-(4-methoxyphenyl)ethenyl]-1-methylpyridinium iodide；4-(4-methoxy-trans-styryl)-1-methyl-pyridinium; iodide；4-(4-Methoxy-trans-styryl)-1-methyl-pyridinium; Jodid；4-[(E)-2-(4-methoxyphenyl)ethenyl]-1-methylpyridin-1-ium iodide；4-[(E)-2-(4-methoxyphenyl)ethenyl]-1-methylpyridin-1-ium;iodide
• CAS: 95495-29-7
• 化学式: C₁₅H₁₆NO*I
• 分子量: 353.203
• InChiKey: VOBZRAJMAYTJPT-BJILWQEISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.31
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[2-(4-methoxyphenyl)ethenyl]-N-methylpyridinium iodide 以 四氢呋喃 为溶剂， 生成 cis-1-methyl-4-methoxy-stilbazolium iodide
  参考文献：
  名称：

  Charge transfer fluorescence of trans-stryrylpyridinium iodides

  摘要：

  The photoprocesses of trans-1-methyl-4-[4-R-styryl]pyridinium iodide (R = H, P1) and derivatives with a cyano, a nitro and a methoxy group at the phenyl moiety, P2-P4, respectively, were studied in solution. In solvents of relatively low polarity, e.g. tetrahydrofuran, where contact ion pairs are present, the fluorescence spectrum of the styrylpyridinium is significantly red-shifted and the quantum yield is strongly enhanced. These findings are due to photoinduced electron transfer from I- to the excited singlet state of the cation. The features of complementary trans-styrylquinolinium iodides are in good accordance. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2010.12.019
• 作为产物：
  描述：

  (E)-4-(4-methoxystyryl)pyridine 、 碘甲烷 以 硝基苯 为溶剂， 生成 4-[2-(4-methoxyphenyl)ethenyl]-N-methylpyridinium iodide
  参考文献：
  名称：

  Ananthakrishnanadar, P.; Rajasekaran, K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 4, p. 324 - 325

  摘要：

  DOI：

文献信息

• Fluorescent neuroactive probes based on stilbazolium dyes
  作者：Adrienne S. Brown、Lisa-Marie Bernal、Teresa L. Micotto、Erika L. Smith、James N. Wilson

  DOI：10.1039/c0ob00849d

  日期：——

  A set of spectrally diverse stilbazolium dyes was identified in an uptake assay using cultured brainstem and cerebellum cells isolated from e19 chicks. Pretreatment of cells with indatraline, a monoamine reuptake inhibitor, allowed identification of dyes that may interact with monoamine transporters. Two structurally related, yet spectrally segregated, probes, (E)-1-methyl-4-[2-(2-naphthalenyl)ethenyl]-pyridinium iodide (NEP+, 3A) and (E)-4-[2-(6-hydroxy-2-naphthalenyl)ethenyl]-1-methyl-pyridinium iodide (HNEP+, 4A), were selected and further investigated using HEK-293 cells selectively expressing dopamine, norepinephrine or serotonin transporters. HNEP+ was selectively accumulated viacatecholamine transporters, with the norepinephrine transporter (NET) giving the highest response; NEP+ was not transported, though possible binding was observed. The alternate modes of interaction enable the use of NEP+ and HNEP+ to image distinct cell populations in live brain tissue explants. The preference for HNEP+ accumulation viaNET was confirmed by imaging uptake in the absence and presence of desipramine, a norepinephrine reuptake inhibitor.

  利用从 e19 雏鸡分离的脑干和小脑培养细胞进行摄取试验，鉴定了一组光谱多样的苯并唑鎓染料。用单胺再摄取抑制剂吲达曲林对细胞进行预处理，从而鉴定出可能与单胺转运体相互作用的染料。(E)-1-甲基-4-[2-(2-萘基)乙烯基]-吡啶鎓碘化物（NEP+，3A）和(E)-4-[2-(6-羟基-2-萘基)乙烯基]-1-甲基吡啶鎓碘化物（HNEP+、4A），并使用选择性表达多巴胺、去甲肾上腺素或血清素转运体的 HEK-293 细胞进行了进一步研究。HNEP+ 在乙酰胆碱转运体中选择性积累，去甲肾上腺素转运体（NET）的反应最高；NEP+ 没有转运，但观察到可能的结合。通过交替的相互作用模式，NEP+ 和 HNEP+ 可以对活体脑组织外植体中的不同细胞群进行成像。通过对去甲肾上腺素再摄取抑制剂地西帕明不存在和存在时的摄取成像，证实了 HNEP+ 通过 NET 聚集的偏好。
• CONDENSATION OF AROMATIC ALDEHYDES WITH γ-PICOLINE METHIODIDE
  作者：ARTHUR P. PHILLIPS

  DOI：10.1021/jo01154a017

  日期：1949.3
• Photoinduced electron transfer vs. trans .fwdarw. cis photoisomerization of quaternary salts of 4-substituted 4'-azastilbenes (R = CN, H, CH3, and OCH3) and their quinolinium analogs. 10
  作者：Helmut. Goerner

  DOI：10.1021/j100291a042

  日期：1987.3
• 4-[2-(4-Methoxyphenyl)ethenyl]-<i>N</i>-methylpyridinium tetraphenylborate
  作者：Shu-Jin Li、De-Chun Zhang、Zhong-Lin Huang、Yan-Qiu Zhang、Kai-Bei Yu

  DOI：10.1107/s0108270100007538

  日期：2000.9.15

  In the cation of the title compound, C15H16NO+. C24H20B-, the pyridyl ring makes a dihedral angle of 14.03 degrees with the phenyl ring. The anion has a slightly distorted tetrahedral geometry and forms honeycomb-like sheets which extend along the b axis, forming channels containing the cations. A comparison of packing energies reveals a difference between the title compound and a similar material which has non-linear optical properties.
• MITTEL ZUM FÄRBEN VON KERATINHALTIGEN FASERN
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP1235549A1

  公开（公告）日：2002-09-04