1-[3-(5-乙酰基-2,3-二甲氧基-苯基)-4,5-二甲氧基-苯基]乙酮 | 55919-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[3-(5-乙酰基-2,3-二甲氧基-苯基)-4,5-二甲氧基-苯基]乙酮
• 英文名称: 1,1'-(5,5',6,6'-tetramethoxy-1,1'-biphenyl-3,3'-diyl)diethanone
• 英文别名: 1-[3-(5-Acetyl-2,3-dimethoxyphenyl)-4,5-dimethoxyphenyl]ethanone
• CAS: 55919-72-7
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: UFABOERRPFSOJD-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[3-(5-乙酰基-2,3-二甲氧基-苯基)-4,5-二甲氧基-苯基]乙酮 在 sodium hydride 、 potassium hydroxide 作用下， 以 乙醇 、 甲苯 、 mineral oil 为溶剂， 反应 17.0h， 生成 4-[5'-(3-carboxy-3-hydroxyacryloyl)-5,6,2',3'-tetramethoxybiphenyl-3-yl]-2-hydroxy-4-oxo-but-2-enoic acid
  参考文献：
  名称：

  Dettori, Maria Antonietta; Fabbri, Davide; Pisano, Marina, Letters in drug design and discovery, 2015, vol. 12, # 2, p. 131 - 139

  摘要：

  DOI：
• 作为产物：
  描述：

  diapocynin 、 碘甲烷 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以40%的产率得到1-[3-(5-乙酰基-2,3-二甲氧基-苯基)-4,5-二甲氧基-苯基]乙酮
  参考文献：
  名称：

  立体选择性恶唑硼烷-硼烷还原联苯烷基二酮-木质素的模型：对映体纯的脱氢二嘧啶醇衍生物

  摘要：

  2个构象柔性联苯烷基二酮的不对称还原9和10与（[R）-oxazaborolidine 3 -硼烷系统成功地进行了与相应的联苯醇11和12以高收率和EE获得与纯手性的优势（小号，小号）双卡宾醇。通过晶体学分析确定了非对映体脱氢二嘧啶醇衍生物（S，S）-14的绝对构型，这证实了CBS催化的酮还原的已知立体化学过程，并提供了有关空间排列的有用信息。

  DOI：

  10.1016/s0957-4166(03)00449-x

文献信息

• Synthesis and Studies of the Inhibitory Effect of Hydroxylated Phenylpropanoids and Biphenols Derivatives on Tyrosinase and Laccase Enzymes
  作者：Maria Antonietta Dettori、Davide Fabbri、Alessandro Dessì、Roberto Dallocchio、Paola Carta、Claudia Honisch、Paolo Ruzza、Donatella Farina、Rossana Migheli、Pier Andrea Serra、Roberto A. Pantaleoni、Xenia Fois、Gaia Rocchitta、Giovanna Delogu

  DOI：10.3390/molecules25112709

  日期：——

  the viability of the new compounds was assayed on PC12 cells, four of which showed a viability of roughly 80% at 40 µM. In silico studies on the crystal structure of laccase enzyme identified a hydroxylated biphenyl bearing a prenylated chain as the lead structure, which activated strong and effective interactions at the active site of the enzyme. These data were confirmed by in vivo experiments performed

  酪氨酸酶和漆酶活性受损会引起哺乳动物、昆虫和微生物生命周期中的严重问题。对这两种酶抑制剂的研究可能会导致发现增白剂、医药产品、抗褐变物质和用于控制有害昆虫和细菌的化合物。使用天然存在的化合物制备了一小部分具有苯丙烷和羟基化联苯核心的新型可逆酪氨酸酶和漆酶抑制剂，并通过分光光度法和电化学测定法测量了它们的活性。构建了基于酪氨酸酶和漆酶酶的生物传感器，用于检测蛋白质-配体相互作用的类型和半数最大抑制浓度 (IC50)。大多数抑制剂对酪氨酸酶的 IC50 为 20-423 nM，对漆酶的 IC50 为 23-2619 nM。由于传统酪氨酸酶和漆酶抑制剂的安全问题，在 PC12 细胞上测定了新化合物的活力，其中四种在 40 µM 下显示出大约 80% 的活力。对漆酶晶体结构的计算机模拟研究确定了带有异戊二烯化链的羟基化联苯作为先导结构，它在酶的活性位点激活了强大而有效的相互作用。这些数据通过在昆虫
• Stereoselective oxazaborolidine–borane reduction of biphenyl methyl diketones: influence of biphenyl substitution pattern
  作者：Giovanna Delogu、Maria Antonietta Dettori、Angela Patti、Sonia Pedotti

  DOI：10.1016/j.tet.2004.08.066

  日期：2004.11

  The stereoselective oxazaborolidine-borane reduction of biphenyl methyl diketones with different substitution patterns on the biaryl unit was investigated, with the aim to better rationalize the factors influencing the diastereo- and enantioselectivity of the reaction for this class of compounds. The observed stereoselectivity in the reduction of diketones 6 and 7, possessing a methoxy group in the meta position with respect to the carbonyl group, is clearly dependent on the experimental conditions. The presence of an asymmetric centre in the intermediate hydroxyketone influences the global stereoselectivity in the reduction of 5 and 6, as indicated from the different selectivity ratios determined for each step of reaction. (C) 2004 Elsevier Ltd. All rights reserved.
• Lignin Model Compounds: 4,4'-<i>O</i>-Dimethyldehydrodiacetovanillone and 4,4'-<i>O</i>-Diethyldehydrodiacetovanillone
  作者：M. A. Ferreira、M. D. D. Costa、I. M. C. Mendes、M. G. Drumond、D. Piló-Veloso、N. G. Fernandes

  DOI：10.1107/s0108270197018015

  日期：1998.6.15

  The title compounds, 5,5'-diacetyl-2,2',3,3'-tetramethoxy-1,1'-biphenyl, C20H22O6, and 5,5'-diacetyl-2,2'-diethoxy-3,3'- dimethoxy-1,1'-biphenyl (IUPAC nomenclature), C22H26O6, correspond to the 5,5'-biphenyl-type lignin model compound. They were synthesized from dehydrodiacetovanillone by alkylation with CH3I and C2H5I, In the former compound, all non-H atoms in the asymmetric unit are planar except for one C atom. In the latter compound, there are two molecules of different conformations, one of which is affected by disorder.
• Stereoselective oxazaborolidine–borane reduction of biphenyl alkyl diketones–lignin models: enantiopure dehydrodiapocynol derivatives
  作者：Giovanna Delogu、Maria Antonietta Dettori、Angela Patti、Sonia Pedotti、Alessandra Forni、Gianluigi Casalone

  DOI：10.1016/s0957-4166(03)00449-x

  日期：2003.8

  Asymmetric reduction of two conformationally flexible biphenyl alkyl diketones 9 and 10 with (R)-oxazaborolidine 3-borane system was successfully carried out and the corresponding biphenyl alcohols 11 and 12 were obtained in high yield and e.e. with predominance of the homochiral (S,S) dicarbinols. The absolute configuration of diastereopure dehydrodiapocynol derivative (S,S)-14 was assigned by crystallographic

  2个构象柔性联苯烷基二酮的不对称还原9和10与（[R）-oxazaborolidine 3 -硼烷系统成功地进行了与相应的联苯醇11和12以高收率和EE获得与纯手性的优势（小号，小号）双卡宾醇。通过晶体学分析确定了非对映体脱氢二嘧啶醇衍生物（S，S）-14的绝对构型，这证实了CBS催化的酮还原的已知立体化学过程，并提供了有关空间排列的有用信息。
• Dettori, Maria Antonietta; Fabbri, Davide; Pisano, Marina, Letters in drug design and discovery, 2015, vol. 12, # 2, p. 131 - 139
  作者：Dettori, Maria Antonietta、Fabbri, Davide、Pisano, Marina、Rozzo, Carla、Palmieri, Giuseppe、Dessì, Alessandro、Dallocchio, Roberto、Delogu, Giovanna

  DOI：——

  日期：——