1-(3,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane | 56177-97-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane
• 英文别名: 1,2-dimethoxy-4-(3-(3,4,5-trimethoxyphenyl)propyl)benzene；1-(3,4-Dimethoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propan；5-[3-(3,4-Dimethoxyphenyl)propyl]-1,2,3-trimethoxybenzene
• CAS: 56177-97-0
• 化学式: C₂₀H₂₆O₅
• 分子量: 346.423
• InChiKey: AJVNBLBGBMAAMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane 生成 1-(2,6-dibromo-3,4,5-trimethoxy-phenyl)-3-(2,3,6-tribromo-4,5-dimethoxy-phenyl)-propane
  参考文献：
  名称：

  Experiments in the Colchicine Field. V. The Thermal and Photochemical Decomposition of Various 2-(β-Phenylethyl)-phenyldiazomethanes and 2-(γ-Phenylpropyl)-phenyldiazomethanes¹

  摘要：

  DOI：

  10.1021/ja01554a043
• 作为产物：
  描述：

  化合物MD2-IN-1 在 盐酸 、 sodium tetrahydroborate 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 1-(3,4-dimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane
  参考文献：
  名称：

  Syntheses of 2-methoxyestradiol and eugenol template based diarylpropenes as non-steroidal anticancer agents

  摘要：

  基于2-甲氧基雌二醇（1）和丁子香酚（6）模板，合成了构象灵活和刚性的二芳基丙烯类化合物14(a–l)与20(a–e)，作为非甾体抗肿瘤药物。采用SRB法评估了这些合成化合物在体外对人癌细胞系MCF-7、A549、DU 145、KB和MDA-MB-231的抗肿瘤活性。化合物14i、14k和15a在不同癌细胞系中显示显著的抗肿瘤活性，IC50值介于10.27 μM至27.91 μM之间。活性最高的分子14k通过诱导凋亡和阻滞细胞周期于G2/M期来抑制细胞增殖。在正常肝单核细胞（THP-1）中进行的体外毒性测试显示，这些化合物（14i、14k和15a）对癌细胞与健康细胞具有高度的选择性。

  DOI：

  10.1039/c4ra03823a

文献信息

• A Novel and Useful Oxidative Intramolecular Coupling Reaction of Phenol Ether Derivatives on Treatment with a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid
  作者：Hiromi Hamamoto、Gopinathan Anilkumar、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1002/1521-3765(20021202)8:23<5377::aid-chem5377>3.0.co;2-h

  日期：2002.12.2

  The oxidative intramolecular coupling reaction of phenol ether derivatives (nonphenolic derivatives) on treatment with a novel combination of a hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) was studied. Biaryl compounds were obtained in excellent yields on treatment of highly substituted phenol ethers. On the other hand, spirodienones were specifically

  研究了酚醚衍生物（非酚类衍生物）在高价碘试剂，苯基碘双三氟乙酸酯（PIFA）和杂多酸（HPA）的新型组合下的氧化分子内偶联反应。通过处理高度取代的酚醚，可以以极好的收率获得联芳基化合物。另一方面，当优选的芳基偶联位点之一在对位被甲氧基取代时，特异形成螺二烯酮。
• Non-phenolic oxidative coupling of phenol ether derivatives using phenyliodine(III) bis(trifluoroacetate)
  作者：Yasuyuki Kita、Michiyo Gyoten、Makoto Ohtsubo、Hirofumi Tohma、Takeshi Takada

  DOI：10.1039/cc9960001481

  日期：——

  Phenol ether derivatives (non-phenolic derivatives), 1,3-diarylpropanes 1a–e, N-benzyl-N-phenethylamines 2a–c and N,N-dibenzylamines 3a–e react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate)(PIFA), containing BF3·Et2O in CH2Cl2 to give the biaryl coupling products 4a–e, 5a–c and 6a–e in good yields.

  苯酚醚衍生物（非酚类衍生物）、1,3-二元丙烷 1a-e、N-苄基-N-苯乙胺 2a-c 和 N,N-二苄胺 3a-e 在 CH2Cl2 中与含有 BF3-Et2O 的高价碘试剂苯基碘（III）双（三氟乙酸盐）（PIFA）发生反应，以良好的收率得到双芳基偶联产物 4a-e、5a-c 和 6a-e。
• A novel and efficient oxidative biaryl coupling reaction of phenol ether derivatives using a combination of hypervalent iodine(iii) reagent and heteropoly acid
  作者：Hiromi Hamamoto、Gopinathan Anilkumar、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1039/b111178g

  日期：2002.2.27

  A novel and efficient oxidative biaryl coupling reaction of phenol ether derivatives using a combination of hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), and heteropoly acid has been developed.

  已经开发了一种新型的高效苯酚醚衍生物的氧化联芳基偶合反应，该反应是结合使用高价碘（III）试剂，苯基碘（III）双（三氟乙酸酯）（PIFA）和杂多酸。
• Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent
  作者：Takeshi Takada、Mitsuhiro Arisawa、Michiyo Gyoten、Ryuji Hamada、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1021/jo980704f

  日期：1998.10.1

  The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a-e), N-benzyl-N-phenethylamines (2a-c) and N,N-dibenzylamines (3a-e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3. Et2O in CH2Cl2 to give the biaryl coupling products (4-6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12-15), whose side chain moiety could be easily cleaved by the known method to give 2,2'-substituted biphenyl compounds (16-18).