6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]-5'-carbaldehyde | 1160838-28-7

• 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: 6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]-5'-carbaldehyde
• 英文别名: 5'-formyl-6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]；6'-nitro-1,3,3-trimethyl-5-formylspiro(indolino-2,2'-[2H]-chromene)；6'-nitro-1,3,3-trimethyl-5-formylspiro(indole-2,2'-[2H]-chromene)；6'-nitro-1,3,3-trimethyl-5-formylspiro(indolino-2,2'-2H-chromene)；1',3',3'-Trimethyl-6-nitrospiro[chromene-2,2'-indole]-5'-carbaldehyde；1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indole]-5'-carbaldehyde
• CAS: 1160838-28-7
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: HJCHJMVHVGCSJU-UHFFFAOYSA-N

物化性质

• 沸点：
  546.4±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]-5'-carbaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 5'-ethynyl-1',3',3'-trimethyl-6-nitrospiro[chromene-2,2'-indoline]
  参考文献：
  名称：

  Ethynyl-equipped Spirobenzopyrans as Promising Photochromic Markers for Nucleic Acid Fragments

  摘要：

  New photochromic markers for nucleic acid fragments, 6'-nitro-substituted spirobenzopyrans equipped with ethynyl group through the appropriate linkers, were subjected to the Sonogashira coupling with model 5-iodo-1,3-dimethyluracil.

  DOI：

  10.1016/j.mencom.2013.05.008
• 作为产物：
  描述：

  乌洛托品 、 螺[1,3,3-三甲基吲哚-(6'-硝基苯并二氢吡喃)] 在 三氟乙酸 作用下， 以80%的产率得到6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]-5'-carbaldehyde
  参考文献：
  名称：

  Synthesis and studies of photochromic properties of spirobenzopyran carboxy derivatives and their model compounds as potential markers

  摘要：

  合成了一系列光致变色标记物，即含有一个或两个活性羧基的螺吡喃，直接连接或通过一个连接体附着，以及它们的模型衍生物。所获得的化合物通过仪器分析方法进行了表征。采用光谱动力学方法研究了螺吡喃标记物及其模型衍生物在乙醇和甲苯溶液中的行为。

  DOI：

  10.1007/s11172-014-0695-3

文献信息

• Synthesis and study of the photochromic behavior of 3-[6′-nitro-1,3,3-trimethylspiro(indolino-2,2′-[2H]-chromen-5-yl)]propenoic acid and its ethyl ester
  作者：A. V. Laptev、A. Yu. Lukin、N. E. Belikov、R. V. Zemtsov、V. I. Shvets、O. V. Demina、S. D. Varfolomeev、V. A. Barachevskii、A. A. Khodonov

  DOI：10.1134/s0018143910030094

  日期：2010.5

  A new photochromic probe containing a spacer with the reactive carboxyl terminal group at the C5 atom of the photochrome molecule was synthesized. The spectral and kinetic study of the behavior of the new photochromic probes in toluene and ethanol was performed.
• Synthesis of 5,10,15,20-tetra[6' -nitro-1,3,3-trimethylspiro- (indolino-2,2' -2H-chromen-5-yl)]porphyrin and its metal complexes
  作者：Alexey V. Laptev、Dmitrii E. Pugachev、Alexey Yu. Lukin、Andrei V. Nechaev、Nikolay E. Belikov、Olga V. Demina、Petr P. Levin、Andrey A. Khodonov、Andrey F. Mironov、Sergei D. Varfolomeev、Vitalii I. Shvets

  DOI：10.1016/j.mencom.2013.07.006

  日期：2013.7

  A new 5,10,15,20-tetrasubstituted porphyrin containing four 6'-nitro-1,3,3-trimethylspiro(indolino-2,2'-2H-chromene) substituents and its complexes with Zn2+ and Cu2+ ions were prepared and characterized by physicochemical methods of analysis.
• Synthesis and photochromic reaction kinetics of unsaturated spiropyran derivatives
  作者：Olga V. Demina、Peter P. Levin、Nikolay E. Belikov、Alexey V. Laptev、Alexey Yu. Lukin、Valery A. Barachevsky、Vitali I. Shvets、Sergei D. Varfolomeev、Andrey A. Khodonov

  DOI：10.1016/j.jphotochem.2013.06.023

  日期：2013.10

  The absorption spectra and decay kinetics of the ground and triplet states of merocyanine (MC) form of spiropyran vinylogs have been investigated by nanosecond laser flash photolysis techniques in toluene and ethanol. The (MC)-M-3 decays to the ground state MC either by quenching with O-2 or due to the intersystem crossing. Relative quantum yield of both (MC)-M-3 and MC drastically decreases when the terminal polar group is separated from the indoline moiety by the C=C-linker. In the presence of the C=C-linker the replacement of terminal CN by CHO has no effect. The yield of (MC)-M-3 and corresponding MC in ethanol is 5 times smaller than that in toluene solution. (C) 2013 Elsevier B.V. All rights reserved.
• Polyenic spirobenzopyrans: Synthesis and study of photochromic properties
  作者：Alexey Laptev、Alexey Lukin、Nikolay Belikov、Maxim Fomin、Konstantin Zvezdin、Olga Demina、Valery Barachevsky、Sergey Varfolomeev、Vitaly Shvets、Andrey Khodonov

  DOI：10.1016/j.jphotochem.2011.03.014

  日期：2011.7

  Four new retinal analogs on basis of nitro-substituted indoline spiropyran were prepared and the spectral kinetic study of their photochromic properties was carried out. Specific influence of nature and length of polyenic substituents on spectral characteristics of spiropyran forms, efficiency of photochromic transformations and photodegradation was established. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis and studies of photochromic properties of spirobenzopyran carboxy derivatives and their model compounds as potential markers
  作者：A. V. Laptev、A. Yu. Lukin、N. E. Belikov、K. V. Zvezdin、O. V. Demina、V. A. Barachevsky、S. D. Varfolomeev、A. A. Khodonov、V. I. Shvets

  DOI：10.1007/s11172-014-0695-3

  日期：2014.9

  A number of photochromic markers, viz., spirobenzopyrans containing one or two active carboxy groups attached directly or through a spacer, as well as their model derivatives, were synthesized. The obtained compounds were characterized by instrumental methods of analysis. Spectrokinetic methods were used to study the behavior of the spirobenzopyran markers and the model derivatives in solutions in EtOH and toluene.

  合成了一系列光致变色标记物，即含有一个或两个活性羧基的螺吡喃，直接连接或通过一个连接体附着，以及它们的模型衍生物。所获得的化合物通过仪器分析方法进行了表征。采用光谱动力学方法研究了螺吡喃标记物及其模型衍生物在乙醇和甲苯溶液中的行为。