(S)-4-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-indan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (S)-4-benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)-indan-1-one
• 英文别名: (2S)-4-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-2,3-dihydroinden-1-one
• 化学式: C₂₉H₂₄O₃
• 分子量: 420.508
• InChiKey: BBBVODRPSLPZKR-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二乙基-4-溴苯甲酰胺 在 palladium on activated charcoal 、 Adam’s catalyst sodium hydroxide 、 四(三苯基膦)钯 、 氯化亚砜 、 四甲基乙二胺 、 HPLC DIACEL OC column 、 氢气 、 仲丁基锂 、 三溴化硼 、 四氯化钛 、 二异丁基氢化铝 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 174.67h， 生成 (S)-4-benzyl-2-(4-hydroxybenzyl)-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

文献信息

• Design, Synthesis, and Evaluation of the Transition- State Inhibitors of Coelenterazine Bioluminescence:  Probing the Chiral Environment of Active Site
  作者：Hideshi Nakamura、Chun Wu、Satoshi Inouye、Akio Murai

  DOI：10.1021/ja005663v

  日期：2001.2.1
• Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase
  作者：Chun Wu、Hideshi Nakamura、Akio Murai、Satoshi Inouye

  DOI：10.1016/s0040-4020(01)00980-2

  日期：2001.11

  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.