4-Nitro-6-[2-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(E)-ylidene]-cyclohexa-2,4-dienone | 16650-15-0

• 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: 4-Nitro-6-[2-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(E)-ylidene]-cyclohexa-2,4-dienone
• 英文别名: 2,4-Cyclohexadien-1-one, 6-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-4-nitro；(6E)-4-nitro-6-[(2Z)-2-(1,3,3-trimethylindol-2-ylidene)ethylidene]cyclohexa-2,4-dien-1-one
• CAS: 16650-15-0
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: IENILPMDTHYRMT-ZGWWUUILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Nitro-6-[2-[1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(E)-ylidene]-cyclohexa-2,4-dienone 以 乙醇 为溶剂， 生成 螺[1,3,3-三甲基吲哚-(6'-硝基苯并二氢吡喃)]
  参考文献：
  名称：

  1-octadecyl- and 3,3-diphenyl-substituted photochromic indolinospirochromenes

  摘要：

  DOI：

  10.1007/bf00475389

文献信息

• <b>Photoprocesses in Spiropyran-Derived </b><b>Merocyanines</b>
  作者：Alexander K. Chibisov、Helmut Görner

  DOI：10.1021/jp962569l

  日期：1997.6.1

  The photophysical and photochemical properties of a series of spiro[2H-1-benzopyran-2,2'-indoline] compounds (Sp-n)-five of them containing a nitro group in the 6-position of the benzopyran portion (n = 1-5) while two (n = 6, 7) do not-were studied by nanosecond laser photolysis in solution. An intermediate, which is attributed to a photoisomer with cis structure, was observed for 1-5 upon excitation of either the spiropyran form or the trans isomer. The ground state properties of the spiropyran/trans isomer couple are characterized in a variety of solvents, and the activation parameters (e.g., activation energies of 38 and 49 kJ mol(-1) for 1 and 5 in acetone, respectively) of the thermal cis --> trans isomerization were determined. Relative quantum yields of the spiropyran --> trans-merocyanine photocoloration and trans --> cis photoisomerization (Phi(Sp-->t) and Phi(t-->c) respectively) were obtained. Phi(Sp-->t) is substantial for 1-5 in solvents of low polarity but reduced in polar solvents. For 1-5 a short-lived transient (maximum at 420-440 and 560-590 nm, lifetime less than or equal to 10 mu s) was observed and identified as a triplet state. It is suggested that this is the triplet of the trans isomer in equilibrium with the perpendicular triplet conformation. The nitro group strongly enhances the quantum yield of intersystem crossing for the spiropyran, thereby changing the singlet pathway of photocoloration for 6 or 7 into a triplet pathway for 1-5. The trans --> cis photoisomerization for 1-5, despite the presence of the triplet state, is suggested to occur essentially via the singlet state.
• 1-octadecyl- and 3,3-diphenyl-substituted photochromic indolinospirochromenes
  作者：N. P. Samoilova、G. K. Bobyleva、M. P. Gal'bershtam

  DOI：10.1007/bf00475389

  日期：1980.1