4-(3,4-dimethoxyphenyl)butanal | 52417-29-5

• 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-(3,4-dimethoxyphenyl)butanal
• CAS: 52417-29-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HXBRZTGSCVOUQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)butanal 在 三乙基硅烷 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Inhibition of IGF-1R and lipoxygenase by nordihydroguaiaretic acid (NDGA) analogs

  摘要：

  Herein, we pursue the hypothesis that the structure of nordihydroguaiaretic acid (NDGA) can be refined for selective potency against the insulin-like growth factor 1 receptor (IGF-1R) as a potential therapeutic target for breast cancer while diminishing its action against other cellular targets. Thus, a set of NDGA analogs (7a-7h) was prepared and examined for inhibitory potency against IGF-1R kinase and an alternative target, 15-lipoxygenase (15 LOX). The anti-cancer effects of these compounds were determined by their ability to inhibit IGF-1 mediated cell growth of MCF-7 breast cancer cells. The design of the analogs was based upon a cursory Topliss approach in which one of NDGA's aromatic rings was modified with various substituents. Structural modification of one of the two catechol rings of NDGA was found to have little effect upon the inhibitory potency against both kinase activity of the IGF-1R and IGF-1 mediated cell growth of MCF-7 cells. 15-LOX was found to be most sensitive to structural modifications of NDGA. From the limited series of NDGA analogs examined, the compound that exhibited the greatest selectivity for IGF-1 mediated growth compared to 15-LOX inhibition was a cyclic analog 7h with a framework similar to a natural product isolated from Larrea divaricata. The results for 7h are significant because while NDGA displays biological promiscuity, 7h exhibits greater specificity toward the breast cancer target IGF-IR with that added benefit of possessing a 10-fold weaker potency against 15-LOX, an enzyme which has a purported tumor suppressing role in breast cancer. With increased specificity and potency, 7h may serve as a new lead in developing novel therapeutic agents for breast cancer. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.092
• 作为产物：
  描述：

  4-溴黎芦醚 在 palladium on activated charcoal bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氢气 、 二异丙胺 作用下， 反应 4.75h， 生成 4-(3,4-dimethoxyphenyl)butanal
  参考文献：
  名称：

  The enantiospecific Nicholas reaction

  摘要：

  The enantiospecific Nicholas reaction, i.e. cobalt-promoted Friedel-Crafts reaction leading from chiral reactant to chiral product, was demonstrated for the first time.

  DOI：

  10.1016/s0040-4039(00)78489-9

文献信息

• Binuclear Pd(I)–Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes
  作者：Yang Zhang、Sebastian Torker、Michel Sigrist、Nikola Bregović、Paweł Dydio

  DOI：10.1021/jacs.0c09254

  日期：2020.10.21

  is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader

  自 1938 年被发现以来，加氢甲酰化得到了彻底的研究并在工业中得到了广泛的应用（每年超过 107 公吨）。然而，迄今为止，使用成熟的 Rh 或助催化剂精确控制其区域选择性的能力已被证明是难以捉摸的，从而限制了许多具有合成价值的醛的获得。钯催化剂代表了一种有吸引力的替代品，但由于不希望的副加工，它们的使用仍然很少。在这里，我们报告了一种高选择性和异常活性的催化剂系统，该系统由一种新型活化策略驱动，并具有独特的 Pd(I)-Pd(I) 机制，涉及碘化物辅助双核步骤以释放产物。这种方法能够对大范围的烯烃和炔烃（包括敏感的起始材料）进行 β 选择性加氢甲酰化。它的效用在抗肥胖药物利莫那班和抗 HIV 药物 PNU-32945 的合成中得到了证明。在更广泛的背景下，新的机理理解使其他对化学工业具有重要意义的羰基化反应的发展成为可能。
• Bidentate Ligands by Self-Assembly through Hydrogen Bonding: A General Room Temperature/Ambient Pressure Regioselective Hydroformylation of Terminal Alkenes
  作者：Wolfgang Seiche、Alexander Schuschkowski、Bernhard Breit

  DOI：10.1002/adsc.200505174

  日期：2005.10

  room temperature/ambient pressure regioselective hydroformylation of terminal alkenes with low catalyst loadings in good activity. The generality of this catalyst under these conditions was demonstrated for a wide range of structurally diverse alkenes equipped with many important functional groups. Thus, this practical and highly selective hydroformylation protocol, which omits the need for special pressure

  6-DPPon（1）/铑催化剂首次使具有低催化剂负载量且活性良好的末端烯烃在室温/环境压力下进行区域选择性加氢甲酰化。在各种条件下配备许多重要官能团的结构多样的烯烃证明了该催化剂在这些条件下的通用性。因此，这种实用且高度选择性的加氢甲酰化方案无需特殊的压力设备，应在有机合成中得到广泛的应用。
• Micellar Catalysis for Sustainable Hydroformylation
  作者：Francesca Migliorini、Filippo Dei、Massimo Calamante、Samuele Maramai、Elena Petricci

  DOI：10.1002/cctc.202100181

  日期：2021.6.18

  regioselective hydroformylation of terminal alkenes, using cheap commercially available catalysts and ligands, in mild reaction conditions (70 °C, 9 bar, 40 min). The process can take advantages from both micellar catalysis and microwave irradiation to obtain the linear aldehydes as the major or sole regioisomers in good to high yields. The substrate scope is largely explored as well as the application of hydroformylation

  这里报道了一种完全可持续且普遍适用的协议，用于末端烯烃的区域选择性加氢甲酰化，使用廉价的市售催化剂和配体，在温和的反应条件下（70°C，9 巴，40 分钟）。该方法可以利用胶束催化和微波辐射的优势以良好到高产率获得线性醛作为主要或唯一的区域异构体。主要探索了底物范围以及加氢甲酰化与分子内半缩醛化的应用，从而证明了与各种官能团的相容性。该反应即使在大规模时也是有效的，并且催化剂和胶束水相可以重复使用至少5次而不影响反应产率。醛原位转化为相应的 Bertagnini 盐，该盐在反应混合物中沉淀，避免有机溶剂介导的纯化步骤，以获得作为纯化合物的最终醛。
• Thermoregulated Microemulsions by Cyclodextrin Sequestration: A New Approach to Efficient Catalyst Recovery
  作者：Loïc Leclercq、Matthieu Lacour、Samantha H. Sanon、Andreea R. Schmitzer

  DOI：10.1002/chem.200900763

  日期：2009.6.22

  The combination of imidazolium surfactants with α‐cyclodextrins (CDs, in green) was used as a control element in the thermoregulated aqueous olefin hydroformylation. The self‐assembly of the imidazolium surfactants (red) favors the micellization process at high temperatures, whereas at lower temperatures the complexation of the surfactant monomers into the α‐CDs is favored.

  咪唑鎓表面活性剂与α-环糊精（CD，绿色）的组合用作温度调节烯烃加氢甲酰化反应中的控制元素。咪唑类表面活性剂（红色）的自组装有利于高温下的胶束化过程，而在较低温度下，表面活性剂单体向α-CDs的络合是有利的。
• Ring substitution influences oxidative cyclisation and reactive metabolite formation of nordihydroguaiaretic acid analogues
  作者：Isaac Asiamah、Heather L. Hodgson、Katherine Maloney、Kevin J.H. Allen、Ed S. Krol

  DOI：10.1016/j.bmc.2015.09.039

  日期：2015.11

  group of analogues the catechols were less stable than phenols, a single catechol-substituted ring is insufficient to form a dibenzocyclooctadiene lignan, and only compounds possessing a di-catechol could form dibenzocyclooctadienes. This suggests that quinone formation may not be necessary for cyclisation to occur and the intramolecular cyclisation likely involves a radical-mediated rather than an electrophilic

  去甲双氢愈创木酸（NDGA）是一种天然的多酚，具有广泛的药理特性。但是，由于缺乏对它的药理和毒理学途径的了解，阻碍了它的实用性。先前我们证明了在生理pH值下NDGA的氧化环化反应会形成二苯并环辛二烯，该二苯并环辛二烯在氧化为邻位化合物的同时可能具有治疗作用-醌可能介导毒理学性质。在生理相关条件下具有较高环化倾向的NDGA类似物可能具有药理学意义，这推动了这项研究。我们合成了一系列NDGA类似物，旨在研究影响分子内环化过程的结构特征，并有助于了解NDGA自氧化转化为二苯并环辛二烯木脂素的机理。我们确定了所研究的NDGA类似物形成二苯并环辛二烯的能力，并评估了该类似物在pH 7.4下的氧化稳定性以及由NDGA类似物形成的任何二苯并环辛二烯的稳定性。我们发现在类似物组中，儿茶酚的稳定性不如酚。单个邻苯二酚取代的环不足以形成二苯并环辛二烯木脂体，只有具有二邻苯二酚的化合物才能形成二苯并环辛二烯。这