1,2-dihydro-1-(2,2-di(4-fluorophenyl)vinylidene)-2,2-di(4-fluorophenyl)naphtho[2,1-b]furan | 1446175-00-3

• 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-di(4-fluorophenyl)vinylidene)-2,2-di(4-fluorophenyl)naphtho[2,1-b]furan
• CAS: 1446175-00-3
• 化学式: C₃₈H₂₂F₄O
• 分子量: 570.586
• InChiKey: DRISZHDFRPEMOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  43
• 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：
  5

反应信息

• 作为产物：
  描述：

  4,4'-二氟二苯甲酮 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 73.0h， 生成 1,2-dihydro-1-(2,2-di(4-fluorophenyl)vinylidene)-2,2-di(4-fluorophenyl)naphtho[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

• 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.