benzyl 2,3,4-trimethoxyphenyl ketone | 123392-69-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: benzyl 2,3,4-trimethoxyphenyl ketone
• 英文别名: 2,3,4-trimethoxydesoxybenzoin；2-Phenyl-1-(2,3,4-trimethoxyphenyl)ethanone
• CAS: 123392-69-8
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: SNOTUZUFRYOXKK-UHFFFAOYSA-N

物化性质

• 熔点：
  58-59 °C
• 沸点：
  421.1±40.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-trimethoxyphenyl ketone 在 indium(III) triflate 、 hydrazine hydrate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 4.0h， 生成 3-(2,3,4-trimethoxyphenyl)-6-methyl-4-phenylpyridazine
  参考文献：
  名称：

  In(OTf)3-mediated synthesis of substituted pyridazines

  摘要：

  In(OTf)(3) (4c)-mediated one-pot (4+2) cyclocondensation of gamma-alkynones 3 with N2H4(aq) in dioxane affords substituted pyridazines 5 in good yields via a sequential desulfonative or dehydrogenative aromatization. The facile transformation proceeds by a facile synthetic sequence starting with an alpha-propargylation of beta-ketosulfones 1 and a cyclocondensation of gamma-alkynones 3 with N2H4(aq). The method provides a mild and efficient condition. Moreover, this route can be enlarged to multigram scale. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.025
• 作为产物：
  描述：

  2,3,4-trihydroxydesoxybenzoin 生成 benzyl 2,3,4-trimethoxyphenyl ketone
  参考文献：
  名称：

  JAIN, A. C.;PALIWAL, POONAM, INDIAN J. CHEM. B, 27,(1988) N1, C. 985-988

  摘要：

  DOI：

文献信息

• Synthesis, cytotoxic evaluation and molecular docking study of 2-alkylthio-4-(2,3,4-trimethoxyphenyl)-5-aryl-thiazoles as tubulin polymerization inhibitors
  作者：Marjan Salehi、Mohsen Amini、Seyed Nasser Ostad、Gholam Hossein Riazi、Amir Assadieskandar、Bentolhoda Shafiei、Abbas Shafiee

  DOI：10.1016/j.bmc.2013.10.030

  日期：2013.12

  A series of cis-restricted 2-alkylthio-4-(2,3,4-trimethoxyphenyl)-5-aryl-thiazole analogues of combretastatin A-4 were synthesized and investigated for inhibition of cell proliferation against three cancer cell lines, HT-29, MCF-7, and AGS, and a normal mouse fibroblastic cell line, NIH-3T3, using an MTT assay. The biological study showed that 2-(methylthio) substituted compounds showed little cytotoxic activity against the four cell lines. In contrast, the presence of the 2-(benzylthio) group on the thiazole ring resulted in a significant improvement in cytotoxic activity relative to the 2-(methylthio) substituted derivatives. Furthermore, the inhibition of tubulin polymerization by some potent compounds was evaluated. All the compounds studied were moderate tubulin polymerization inhibitors. The flow cytometry analysis confirmed that the synthesized compounds led to cell cycle arrest at the G(2)/M phase. Docking simulation was performed to insert these compounds into the crystal structure of tubulin at the colchicine binding site to determine a probable binding model. (C) 2013 Elsevier Ltd. All rights reserved.
• A Convenient One-Pot Preparative Method for 4,5-Diarylisoxazoles Involving Amine Exchange Reactions
  作者：Esther Domínguez、Estíbaliz Ibeas、Eduardo Martínez de Marigorta、Jon Kepa Palacios、Raul SanMartín

  DOI：10.1021/jo960024h

  日期：1996.1.1

  4,5-Diarylisoxazoles 1 are efficiently prepared by submitting enaminones 2, readily obtained from deoxybenzoins 3, to oximation conditions. This conversion implies an uncommon amine group exchange reaction. Preparation of 4-isoxazolines 5 and ring-opening transformations to beta-keto nitriles 4 and 1,3-amino alcohol derivatives 7 are also described.
• Jain, Amolak C.; Nayyar, Naresh K.; Paliwal, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 10 - 14
  作者：Jain, Amolak C.、Nayyar, Naresh K.、Paliwal, Poonam

  DOI：——

  日期：——
• Jain, A. C.; Paliwal, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 985 - 988
  作者：Jain, A. C.、Paliwal, Poonam

  DOI：——

  日期：——
• JAIN, A. C.;PALIWAL, POONAM, INDIAN J. CHEM. B, 27,(1988) N1, C. 985-988
  作者：JAIN, A. C.、PALIWAL, POONAM

  DOI：——

  日期：——