2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one | 395682-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one
• 英文别名: 2-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-3H-inden-1-one
• CAS: 395682-02-7
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: NUYYUTJUSALBIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one 在 HPLC DIACEL OC column 作用下， 以 乙醇 、 正己烷 为溶剂， 生成 (R)-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one 、 (S)-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one
  参考文献：
  名称：

  Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase

  摘要：

  The bioluminescence reaction of coelenterazine involves an oxidative process. To investigate the reaction mechanism, we synthesized three mechanism-based inhibitors with an indanone core structure. The inhibitors exhibited the competitive inhibition of the Renilla luciferase reaction. The (-)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one showed the significant enantio-selectivity of the inhibition and its absolute configuration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luciferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00980-2
• 作为产物：
  描述：

  6-甲氧基-1-茚酮 在 Adam’s catalyst sodium hydroxide 、 四(三苯基膦)钯 、 氢气 、 三溴化硼 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 76.0h， 生成 2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one
  参考文献：
  名称：

  Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase

  摘要：

  The bioluminescence reaction of coelenterazine involves an oxidative process. To investigate the reaction mechanism, we synthesized three mechanism-based inhibitors with an indanone core structure. The inhibitors exhibited the competitive inhibition of the Renilla luciferase reaction. The (-)-4-benzyl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one showed the significant enantio-selectivity of the inhibition and its absolute configuration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luciferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00980-2