2-hydroxy-3-(diphenylhydroxymethyl)anthracene | 1609021-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-hydroxy-3-(diphenylhydroxymethyl)anthracene
• 英文别名: 3-[Hydroxy(diphenyl)methyl]anthracen-2-ol；3-[hydroxy(diphenyl)methyl]anthracen-2-ol
• CAS: 1609021-27-3
• 化学式: C₂₇H₂₀O₂
• 分子量: 376.455
• InChiKey: QJNQTKXRQMCDSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  613.8±50.0 °C(predicted)
• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-(diphenylhydroxymethyl)anthracene 在 sodium azide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以38%的产率得到3-(azidodiphenylmethyl)anthracen-2-ol
  参考文献：
  名称：

  Near-Visible Light Generation of a Quinone Methide from 3-Hydroxymethyl-2-anthrol

  摘要：

  Excitation of 2-hydroxy-3-(diphenylhydroxymethyl)-anthracene (7) to SI initiates photodehydration, giving the corresponding quinone methide (QM) that was detected by laser flash photolysis (LFP) in 2,2,2-trifluoroethanol (lambda = 580 nm, tau = 690 +/- 10 ns). The QM decays by protonation, giving a cation (lambda = 520 nm, tau = 84 +/- 3 ps), which subsequently reacts with nucleophiles. The rate constants in the reactions with nucleophiles were determined by LFP, whereas the adducts were isolated via preparative photolyses. The photogeneration of QMs in the anthrol series is important for potential use in biological systems since the chromophore absorbs at wavelengths > 400 nm. Antiproliferative investigations conducted with 2-anthrol derivative 7 on three human cancer cell lines showed higher activity for irradiated cells.

  DOI：

  10.1021/jo500290y
• 作为产物：
  描述：

  2-羟基蒽醌 在 sodium tetrahydroborate 、 正丁基锂 、 溴 、 异丙醇 作用下， 以 乙醚 、 正己烷 、 水 、 溶剂黄146 为溶剂， 反应 20.75h， 生成 2-hydroxy-3-(diphenylhydroxymethyl)anthracene
  参考文献：
  名称：

  Near-Visible Light Generation of a Quinone Methide from 3-Hydroxymethyl-2-anthrol

  摘要：

  Excitation of 2-hydroxy-3-(diphenylhydroxymethyl)-anthracene (7) to SI initiates photodehydration, giving the corresponding quinone methide (QM) that was detected by laser flash photolysis (LFP) in 2,2,2-trifluoroethanol (lambda = 580 nm, tau = 690 +/- 10 ns). The QM decays by protonation, giving a cation (lambda = 520 nm, tau = 84 +/- 3 ps), which subsequently reacts with nucleophiles. The rate constants in the reactions with nucleophiles were determined by LFP, whereas the adducts were isolated via preparative photolyses. The photogeneration of QMs in the anthrol series is important for potential use in biological systems since the chromophore absorbs at wavelengths > 400 nm. Antiproliferative investigations conducted with 2-anthrol derivative 7 on three human cancer cell lines showed higher activity for irradiated cells.

  DOI：

  10.1021/jo500290y

文献信息

• Near-Visible Light Generation of a Quinone Methide from 3-Hydroxymethyl-2-anthrol
  作者：Đani Škalamera、Kata Mlinarić-Majerski、Irena Martin-Kleiner、Marijeta Kralj、Peter Wan、Nikola Basarić

  DOI：10.1021/jo500290y

  日期：2014.5.16

  Excitation of 2-hydroxy-3-(diphenylhydroxymethyl)-anthracene (7) to SI initiates photodehydration, giving the corresponding quinone methide (QM) that was detected by laser flash photolysis (LFP) in 2,2,2-trifluoroethanol (lambda = 580 nm, tau = 690 +/- 10 ns). The QM decays by protonation, giving a cation (lambda = 520 nm, tau = 84 +/- 3 ps), which subsequently reacts with nucleophiles. The rate constants in the reactions with nucleophiles were determined by LFP, whereas the adducts were isolated via preparative photolyses. The photogeneration of QMs in the anthrol series is important for potential use in biological systems since the chromophore absorbs at wavelengths > 400 nm. Antiproliferative investigations conducted with 2-anthrol derivative 7 on three human cancer cell lines showed higher activity for irradiated cells.