4-[2-(2-hydroxyethoxy)ethoxy]-3,5-dimethoxybenzaldehyde | 864161-30-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(2-hydroxyethoxy)ethoxy]-3,5-dimethoxybenzaldehyde
• CAS: 864161-30-8
• 化学式: C₁₃H₁₈O₆
• mdl: MFCD16354156
• 分子量: 270.282
• InChiKey: LFVYWKWHMPLGFE-UHFFFAOYSA-N

物化性质

• 沸点：
  446.7±45.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[2-(2-hydroxyethoxy)ethoxy]-3,5-dimethoxybenzaldehyde 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 cis-16,19-dimethoxy-8,11,14-trioxatricyclo[13.2.2.2^4,7]henicosa-1(17),4,6,15,18,20-hexaene-2,3,6-triyl triacetate
  参考文献：
  名称：

  p,p-Dihydroxydihydrostilbenophanes Related to Antimitotic Combretastatins. Conformational Analysis and Its Relationship to Tubulin Inhibition

  摘要：

  The structures of a new family of macrocyclic analogues of combretastatins B combining oxygenated substituents on the phenyl rings and indole rings are described. The effects of the stereochemistry, of the length of the spacer linking both aryl groups, and of the decoration of the macrocycles on the kinematics of the system have been studied by means of NMR studies at several temperatures and in different solvents combined with theoretical studies including Monte Carlo conformational searches and molecular dynamics simulations at different temperatures. The new indole macrocycles provide a more rigid view of this kind of macrocycles than that previously held. The tubulin polymerization activity of this new class of macrocycles has been assayed and analyzed.

  DOI：

  10.1021/jo500798r
• 作为产物：
  描述：

  丁香醛 、 二乙二醇 在 triphenylphosphine resin 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 4-[2-(2-hydroxyethoxy)ethoxy]-3,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  对位之间连接的大环二羟基苯乙烯的合成和构象分析。

  摘要：

  已经合成了新的二苯乙烷家族，作为抗有丝分裂康维他汀的构象受限类似物。两个苯环通过3-氧杂戊基亚甲基或六亚甲基链连接在对苯酚位置之间。通过使用连接的芳族二醛的分子内McMurry频哪醇偶联，除硝基取代的化合物外，以中等收率实现了关键的大环化步骤。异构体频哪醇的相对立体化学是通过光谱学，化学衍生化和分子建模方法的组合来确定的。这些化合物的核磁共振谱（带有多加氧的冠环烷骨架）表明相对于其母体康他汀具有严格的构象限制。

  DOI：

  10.1002/chem.200700323

文献信息

• New para-para Stilbenophanes: Synthesis by McMurry Coupling, Conformational Analysis and Inhibition of Tubulin Polymerisation
  作者：Raquel Álvarez、Vilmarí López、Carmen Mateo、Manuel Medarde、Rafael Peláez

  DOI：10.1002/chem.201002869

  日期：2011.3.14

  The synthesis of a new family of methoxy‐substituted [2.7]‐ and [2.8]paracyclophanes linked by 3‐oxapentamethylene‐1,5‐dioxy and hexamethylene‐1,6‐dioxy bridges has been carried out by using the McMurry methodology. Related indole compounds were also synthesised. Olefin‐to‐diol ratios depended on the bridge length, the structure of the aromatic ring and the reaction conditions. Macrocyclisation, the

  通过使用McMurry方法，合成了由3-氧杂戊基亚甲基-1,5-二氧基和六亚甲基-1,6-二氧基桥连接的新的甲氧基取代的[2.7]-和[2.8]对环环烷家族。还合成了相关的吲哚化合物。烯烃与二醇的比例取决于桥的长度，芳环的结构和反应条件。如通过NMR光谱法和根据理论计算所观察到的，大环化，甲氧基取代基和刚性吲哚部分的存在限制了构象平衡。合成的化合物显示微摩尔微管蛋白聚合抑制活性。与康布雷他汀，密切相关的斯蒂芬类相比，对大环化产生的微管蛋白聚合抑制活性的构象影响
• DENDRITIC NANO-ANTIOXIDANTS
  申请人：Lee Choon Young

  公开号：US20100247439A1

  公开（公告）日：2010-09-30

  Provided are dendritic nano-antioxidant compounds according to Formula I, which may further comprise active agents covalently or non-covalently attached. Further provided are compositions comprising the disclosed compounds. Also disclosed are cosmetic compositions and dietary supplements comprising the compounds according to Formula I. The invention additionally provides methods of reducing free radicals or oxidative stress in a cell, a method of treating a subject, and a method of treating a condition comprising administering the compounds according to Formula I.

  本发明提供了公式I的树突型纳米抗氧化化合物，该化合物可以进一步包含共价或非共价附着的活性剂。还提供了包含所述化合物的组合物。还公开了包含公式I的化合物的化妆品组合物和膳食补充剂。此外，本发明还提供了减少细胞中自由基或氧化应激的方法，治疗受试者的方法以及治疗包括给予公式I的化合物的病症的方法。
• Stilbenophane Analogues of Deoxycombretastatin A-4
  作者：Carmen Mateo、Concepción Pérez-Melero、Rafael Peláez、Manuel Medarde

  DOI：10.1021/jo0508393

  日期：2005.8.1

  A new family of polyoxygenated stilbenophanes has been synthesized as conformationally restricted analogues of antimitotic combretastatins. By means of the McMurry olefination process, compounds derived from diethyleneglycol and 1,6-hexanediol were obtained, whereas Grubbs'catalyst failed in producing the ring-closing metathesis to this kind of macrocyclic products.
• US8895032B2
  申请人：——

  公开号：US8895032B2

  公开（公告）日：2014-11-25
• Synthesis and Conformational Analysis of Macrocyclic Dihydroxystilbenes Linked between thepara–para Positions
  作者：Carmen Mateo、Vilmarí López、Manuel Medarde、Rafael Peláez

  DOI：10.1002/chem.200700323

  日期：2007.8.27

  3-oxapentamethylene or hexamethylene chain. The key macrocyclization step was achieved in moderate yields by using an intramolecular McMurry pinacol coupling of linked aromatic dialdehydes, except for the nitro-substituted compounds. The relative stereochemistry of the isomeric pinacols was determined by a combination of spectroscopic, chemical derivatization, and molecular-modeling approaches. The NMR

  已经合成了新的二苯乙烷家族，作为抗有丝分裂康维他汀的构象受限类似物。两个苯环通过3-氧杂戊基亚甲基或六亚甲基链连接在对苯酚位置之间。通过使用连接的芳族二醛的分子内McMurry频哪醇偶联，除硝基取代的化合物外，以中等收率实现了关键的大环化步骤。异构体频哪醇的相对立体化学是通过光谱学，化学衍生化和分子建模方法的组合来确定的。这些化合物的核磁共振谱（带有多加氧的冠环烷骨架）表明相对于其母体康他汀具有严格的构象限制。