1',3',3'-trimethyl-1,2-tetramethylenespiro[7H-furo(3,2-f)-(2H-1)-benzopyran-7,2'-indoline] | 183174-06-3

• 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: 1',3',3'-trimethyl-1,2-tetramethylenespiro[7H-furo(3,2-f)-(2H-1)-benzopyran-7,2'-indoline]
• 英文别名: 1',3',3'-Trimethylspiro[8,9,10,11-tetrahydro-[1]benzofuro[3,2-f]chromene-3,2'-indole]
• CAS: 183174-06-3
• 化学式: C₂₅H₂₅NO₂
• 分子量: 371.479
• InChiKey: CYHYIXMPAQQNJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  25.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1',3',3'-trimethyl-1,2-tetramethylenespiro[7H-furo(3,2-f)-(2H-1)-benzopyran-7,2'-indoline] 生成
  参考文献：
  名称：

  Photo-and thermochromic spiranes. 25. New indolinospiropyrans containing a condensed furan fragment

  摘要：

  DOI：

  10.1007/s10593-006-0170-7
• 作为产物：
  描述：

  1,2,3,3-tetramethyl-3H-indolium perchlorate 、 5-hydroxy-2,3-tetramethylenebenzo[b]furan-4-carbaldehyde 在 哌啶 作用下， 以 乙醇 为溶剂， 以74%的产率得到1',3',3'-trimethyl-1,2-tetramethylenespiro[7H-furo(3,2-f)-(2H-1)-benzopyran-7,2'-indoline]
  参考文献：
  名称：

  Novel indolinospiropyrans containing a condensed furan moiety

  摘要：

  DOI：

  10.1007/bf02256926

文献信息

• Furo-fused 2<i>H</i>-chromenes: synthesis and photochromic properties
  作者：Jean-Luc Pozzo、André Samat、Robert Guglielmetti、Vladimir Lokshin、Vladimir Minkin

  DOI：10.1139/v96-182

  日期：1996.9.1

  New photochromic chromenes annulated with a furan ring have been synthesized. Thus, suitable heterocyclic phenols react with different propargylic alcohols in acidic medium to give the corresponding ethers, which cyclize into benzopyrans by thermal Claisen rearrangement. This synthetic approach was found to lead to a mixture of linear and angular chromenes that is strictly related to the nature of

  合成了具有呋喃环的新型光致变色色烯。因此，合适的杂环酚在酸性介质中与不同的炔丙醇反应得到相应的醚，醚通过热克莱森重排环化成苯并吡喃。发现这种合成方法导致线性和有角色烯的混合物，这与苯酚的性质密切相关。然而，区域特异性可以通过 β-苯基肉桂醛在回流的非质子非极性溶剂中与前一种酚的钛 (IV) 盐反应来获得。中间生成的 o-醌结构的电环化发生在朝向杂环结的 α 位置。所有化合物在室温下都表现出光致变色行为。鉴于光致形式的红移和加宽吸收光谱，呋喃稠合苯并吡喃对于萘并吡喃母体特别有趣。这一趋势得到了几个异质...的光谱数据的证实。
• Photochromic Spiro[7H-furo(3,2-f)-(2H-1)-benzopyran-7,2’-indolines]: Experimental and Computational Evidence for the Elusive Intermediate of the Photoinitiated Ring Opening Reaction of Spiropyrans
  作者：A. V. Metelitsa、I. V. Dorogan、B. S. Lukyanov、V. I. Minkin、S. O. Besugliy、J. C. Micheau

  DOI：10.1080/15421400590946154

  日期：2005.5.1

  6-(tert-butyl) derivative 1d , the formation of an acoplanar cis-cisoid intermediate, the lifetime of which at 77 K is long enough to observe its absorption and fluorescence spectra, has been detected. The occurrence of the intermediate on the reaction paths for the thermal and photoinitiated ring-opening processes has been also shown by DFT calculations.

  摘要 1',3',3'-三甲基-1,2-四亚甲基螺[7H-呋喃(3,2-f)-(2H-1)-苯并吡喃-7系列的光致变色行为、吸收和发光光谱,2'-二氢吲哚] 1 进行了研究。在 6-(叔丁基) 衍生物 1d 的情况下，已检测到非共面顺式-顺式中间体的形成，其在 77 K 下的寿命足以观察其吸收和荧光光谱。DFT 计算也显示了在热和光引发开环过程的反应路径上出现中间体。
• Novel indolinospiropyrans containing a condensed furan moiety
  作者：B. S. Luk'yanov、E. N. Shepelenko、V. A. Bren'、A. O. Bulanov

  DOI：10.1007/bf02256926

  日期：2000.7
• Photo-and thermochromic spiranes. 25. New indolinospiropyrans containing a condensed furan fragment
  作者：B. S. Lukyanov、A. N. Utenyshev、E. N. Shepelenko、V. V. Tkachev、M. B. Lukyanova、A. V. Metelitsa、S. O. Bezuglyi、S. M. Aldoshin、V. I. Minkin

  DOI：10.1007/s10593-006-0170-7

  日期：2006.7
• Photo-and thermochromic spiranes 30*. Comparative study by X-ray structural analysis of the structure of spiropyrans of the indoline series containing a condensed furan fragment
  作者：B. S. Lukyanov、A. N. Utenyshev、V. V. Tkachev、S. M. Aldoshin、V. I. Minkin、M. B. Lukyanova、Yu. S. Alekseenko

  DOI：10.1007/s10593-008-0034-4

  日期：2008.2

  The structure of an indoline spiropyran of molecular formula C29H33NO2 has been studied by X-ray crystallographic analysis. Structural parameters have been determined for this spiropyran, containing a condensed furan fragment with a tert-butyl group, in comparison with the structure of other spiropyrans of this series. The observation in the absorption spectrum of a photoinduced cis-cis isomer is linked with its stabilization by the steric effect of the bulky tert-butyl group and the strength of barriers at 77 K.