1,2-dihydro-1-((2,2-diphenyl)vinylidene)-2,2-diphenylnaphtho-[2,1-b]furan | 1446174-99-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 1,2-dihydro-1-((2,2-diphenyl)vinylidene)-2,2-diphenylnaphtho-[2,1-b]furan
• CAS: 1446174-99-7
• 化学式: C₃₈H₂₆O
• 分子量: 498.624
• InChiKey: VAZFNXKPVKRIHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-1-((2,2-diphenyl)vinylidene)-2,2-diphenylnaphtho-[2,1-b]furan 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  仔细观察亚乙烯基-萘呋喃的光致变色

  摘要：

  亚乙烯基-萘呋喃是一类易于合成的新型光致变色分子，其独特的结构结合了与二氢呋喃环相连的烯丙基。这些未着色的分子在吸附在硅胶中或溶解在酸化的醇溶液中后，在溶液中会显示出酸致变色和光致变色特性，但在普通溶剂或固态中则不会。根据对UV辐射的CH 3 OD + THF-d8酸化溶液的NMR分析，提出了一种热可逆的光致变色行为的机理：紫外光促进了向萘呋喃中添加甲醇，从而提供了一组无色的光产物，这些产物逐渐发展为无色化合物P 2。在存在酸的情况下，后者会迅速转化成阳离子紫罗兰色染料，该染料在黑暗中热返回初始的封闭萘并呋喃。该光致变色系统在暴露于紫外线或阳光（15 s）后在无色和紫色状态之间切换，并在黑暗中于室温下2-8分钟内热返回初始无色状态。

  DOI：

  10.1016/j.dyepig.2016.11.001
• 作为产物：
  描述：

  1,1-二苯基-2-丙炔-1-醇 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 23.5h， 生成 1,2-dihydro-1-((2,2-diphenyl)vinylidene)-2,2-diphenylnaphtho-[2,1-b]furan
  参考文献：
  名称：

  Synthesis of 1-Vinylidene-naphthofurans: A Thermally Reversible Photochromic System That Colors Only When Adsorbed on Silica Gel

  摘要：

  A set of new 1-vinylidene-1,2-dihydro-naphtho[2,1-b]furans were unexpectedly obtained in the reaction of 2-naphthol with readily available 1,1,4,4-tetraarylbut-2-yne-1,4-diols. Surprisingly, when adsorbed in silica gel, these compounds exhibit photochromism at room temperature, whereas not in solution and in the solid state. UV or sunlight irradiation leads, in a few seconds, to the formation of intense pink/violet to green colors that bleach completely in a few minutes in the dark. These new compounds also exhibit reversible acidochromic properties in solution: addition of TFA leads to the opening of the furan ring and addition of a proton to the allene function, leading to a conjugated and violet tertiary carbocation that returned immediately to the uncolored allenic structure upon addition of a weak base.

  DOI：

  10.1021/jo400710r

文献信息

• Grey colouring thermally reversible photochromic 1-vinylidene-naphthofurans
  作者：Céu Sousa、Sofia Saraiva、Helena Macedo、Paulo Coelho

  DOI：10.1016/j.dyepig.2017.02.027

  日期：2017.6

  A set of new 1-vinylidene-naphthofurans substituted by styryl groups were synthetized. These compounds show photochromic properties when adsorbed in silica gel, or in acidified THF solutions, developing intense colours after exposure to the UV light and returning to the uncoloured state, in the dark, in several minutes. The introduction of the styryl chain extends the conjugation of the photoproducts

  合成了一组新的被苯乙烯基取代的1-亚乙烯基-萘呋喃。这些化合物吸附在硅胶或酸化的THF溶液中时显示出光致变色特性，在暴露于紫外线后几分钟内会呈现强烈的颜色，并在黑暗中恢复为无色状态。苯乙烯基链的引入扩展了光产物的缀合，并相对于母体未取代的萘并呋喃红移地改变了它们的吸收。对于苯乙烯基萘呋喃5a，在酸化的THF溶液中，暴露于紫外线1分钟（或阳光直射）后，可获得深灰色，而在黑暗中，室温下不到10分钟即可发生脱色。
• A closer look at the photochromism of vinylidene-naphthofurans
  作者：Céu M. Sousa、Jerome Berthet、Stephanie Delbaere、Paulo J. Coelho

  DOI：10.1016/j.dyepig.2016.11.001

  日期：2017.2

  Vinylidene-naphthofurans are a new class of photochromic molecules, easily synthetized, with a unique structure combining an allene group linked to a dihydrofuran ring. These uncoloured molecules show acidochromism in solution and photochromic properties when adsorbed in silica gel or dissolved in acidified alcoholic solutions but not in common solvents or in the solid state. A mechanism for their

  亚乙烯基-萘呋喃是一类易于合成的新型光致变色分子，其独特的结构结合了与二氢呋喃环相连的烯丙基。这些未着色的分子在吸附在硅胶中或溶解在酸化的醇溶液中后，在溶液中会显示出酸致变色和光致变色特性，但在普通溶剂或固态中则不会。根据对UV辐射的CH 3 OD + THF-d8酸化溶液的NMR分析，提出了一种热可逆的光致变色行为的机理：紫外光促进了向萘呋喃中添加甲醇，从而提供了一组无色的光产物，这些产物逐渐发展为无色化合物P 2。在存在酸的情况下，后者会迅速转化成阳离子紫罗兰色染料，该染料在黑暗中热返回初始的封闭萘并呋喃。该光致变色系统在暴露于紫外线或阳光（15 s）后在无色和紫色状态之间切换，并在黑暗中于室温下2-8分钟内热返回初始无色状态。
• Synthesis of 1-Vinylidene-naphthofurans: A Thermally Reversible Photochromic System That Colors Only When Adsorbed on Silica Gel
  作者：Céu M. Sousa、Jerome Berthet、Stephanie Delbaere、Paulo J. Coelho

  DOI：10.1021/jo400710r

  日期：2013.7.19

  A set of new 1-vinylidene-1,2-dihydro-naphtho[2,1-b]furans were unexpectedly obtained in the reaction of 2-naphthol with readily available 1,1,4,4-tetraarylbut-2-yne-1,4-diols. Surprisingly, when adsorbed in silica gel, these compounds exhibit photochromism at room temperature, whereas not in solution and in the solid state. UV or sunlight irradiation leads, in a few seconds, to the formation of intense pink/violet to green colors that bleach completely in a few minutes in the dark. These new compounds also exhibit reversible acidochromic properties in solution: addition of TFA leads to the opening of the furan ring and addition of a proton to the allene function, leading to a conjugated and violet tertiary carbocation that returned immediately to the uncolored allenic structure upon addition of a weak base.