1-benzyloxy-2-(11-hydroxyundecyl)-9,10-anthraquinone | 424801-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-benzyloxy-2-(11-hydroxyundecyl)-9,10-anthraquinone
• 英文别名: 2-(11-Hydroxyundecyl)-1-phenylmethoxyanthracene-9,10-dione
• CAS: 424801-72-9
• 化学式: C₃₂H₃₆O₄
• 分子量: 484.635
• InChiKey: UBBWWBNSUDBNDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-2-(11-hydroxyundecyl)-9,10-anthraquinone 在 铬酸 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以70%的产率得到1-benzyloxy-2-(11-carboxyundecyl)-9,10-anthraquinone
  参考文献：
  名称：

  Photochemical Synthesis of Aldehydes in the Solid Phase

  摘要：

  A substituted anthraquinone (AQ), previously shown to photochemically generate benzaldehyde in methanol solution, was attached to a commercially available resin via an I I carbon tether and an amide bond. Photolysis of the polymer-bound AQ with visible or 350 nm UV light resulted in the formation of benzaldehyde in yields of 50-55% as determined by HPLC. The phenolic positions in the polymer were then alkylated using benzyl bromide and 1-iodo-3-(4-nitrophctiyl)propane in a coupling reaction with K2CO3 as a base and a solution-phase proton shuttle. Photolysis of these alkylated polymers resulted in the formation of benzaldehyde (54-89%) and 3-(4-nitrophenyl)propanal (58-67%). The yields of both aldehydes dropped considerably with subsequent realkylation and photolysis, and the polymer beads began to show signs of deterioration. This is the first time that aldehydes have been made photochemically on a solid-supported phase.

  DOI：

  10.1021/jo025508u
• 作为产物：
  描述：

  10-十一烯醛 在 sodium hydroxide 、 sodium dithionite 、 硼烷四氢呋喃络合物 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丁酮 为溶剂， 反应 77.5h， 生成 1-benzyloxy-2-(11-hydroxyundecyl)-9,10-anthraquinone
  参考文献：
  名称：

  Photochemical Synthesis of Aldehydes in the Solid Phase

  摘要：

  A substituted anthraquinone (AQ), previously shown to photochemically generate benzaldehyde in methanol solution, was attached to a commercially available resin via an I I carbon tether and an amide bond. Photolysis of the polymer-bound AQ with visible or 350 nm UV light resulted in the formation of benzaldehyde in yields of 50-55% as determined by HPLC. The phenolic positions in the polymer were then alkylated using benzyl bromide and 1-iodo-3-(4-nitrophctiyl)propane in a coupling reaction with K2CO3 as a base and a solution-phase proton shuttle. Photolysis of these alkylated polymers resulted in the formation of benzaldehyde (54-89%) and 3-(4-nitrophenyl)propanal (58-67%). The yields of both aldehydes dropped considerably with subsequent realkylation and photolysis, and the polymer beads began to show signs of deterioration. This is the first time that aldehydes have been made photochemically on a solid-supported phase.

  DOI：

  10.1021/jo025508u

文献信息

• Photochemical Synthesis of Aldehydes in the Solid Phase
  作者：Ronald L Blankespoor、Tim DeVries、Eric Hansen、Jeffrey M. Kallemeyn、Aaron M. Klooster、Jason A. Mulder、Robert P. Smart、Douglas A. Vander Griend

  DOI：10.1021/jo025508u

  日期：2002.4.1

  A substituted anthraquinone (AQ), previously shown to photochemically generate benzaldehyde in methanol solution, was attached to a commercially available resin via an I I carbon tether and an amide bond. Photolysis of the polymer-bound AQ with visible or 350 nm UV light resulted in the formation of benzaldehyde in yields of 50-55% as determined by HPLC. The phenolic positions in the polymer were then alkylated using benzyl bromide and 1-iodo-3-(4-nitrophctiyl)propane in a coupling reaction with K2CO3 as a base and a solution-phase proton shuttle. Photolysis of these alkylated polymers resulted in the formation of benzaldehyde (54-89%) and 3-(4-nitrophenyl)propanal (58-67%). The yields of both aldehydes dropped considerably with subsequent realkylation and photolysis, and the polymer beads began to show signs of deterioration. This is the first time that aldehydes have been made photochemically on a solid-supported phase.