1-(hydroxydiphenylmethyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran | 312743-60-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 1-(hydroxydiphenylmethyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran
• 英文别名: {3,3-Diphenyl-3H-benzo[F]chromen-1-YL}diphenylmethanol；(3,3-diphenylbenzo[f]chromen-1-yl)-diphenylmethanol
• CAS: 312743-60-5
• 化学式: C₃₈H₂₈O₂
• mdl: MFCD00309874
• 分子量: 516.639
• InChiKey: ZZEJVJNTVPUIBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(1-hydroxy-1,1,4,4-tetraphenylbuta-2,3-dien-2-yl)-naphthalen-2-ol 以 氘代氯仿 为溶剂， 生成 1-(hydroxydiphenylmethyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran
  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.