4-(3,4-dimethoxyphenyl)butan-1-ol | 56880-86-5

• 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)butan-1-ol
• 英文别名: 3,4-Dimethoxy-benzenebutanol
• CAS: 56880-86-5
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: HGTHHDQDYLRWAH-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C(Solv: ethyl ether (60-29-7); pentane (109-66-0))
• 沸点：
  155-157 °C(Press: 3 Torr)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)butan-1-ol 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 4.5h， 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)butan-1-ol
  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

• A novel synthesis of (di)-benzazocinones via an endocyclic N-acyliminium ion cyclisation
  作者：Frank D. King、Abil E. Aliev、Stephen Caddick、D. A. Tocher

  DOI：10.1039/c0ob00559b

  日期：——

  The triflic acid-mediated endocyclic N-acyliminium ion cyclisation provides a facile synthesis of (di)-benzazocinones. On reduction of the 10-phenyl derivative, an unusually non-polar tertiary alkylamine was obtained.

  三氟甲磺酸介导的环内N-酰亚胺离子环化反应提供了一种简便合成（二）苯并吖啶酮的方法。将10-苯基衍生物还原后，获得了一个异常非极性的三烷基胺。
• Synthesis and Biological Studies of Novel 2-Aminoalkylethers as Potential Antiarrhythmic Agents for the Conversion of Atrial Fibrillation
  作者：Bertrand Plouvier、Gregory N. Beatch、Grace L. Jung、Alexander Zolotoy、Tao Sheng、Lilian Clohs、Terrance D. Barrett、David Fedida、Wei Q. Wang、Jeff J. Zhu、Yuzhong Liu、Shlomo Abraham、Leah Lynn、Ying Dong、Richard A. Wall、Michael J. A. Walker

  DOI：10.1021/jm0604528

  日期：2007.6.1

  A series of 2-aminoalkylethers prepared as potential antiarrhythmic agents is described. The present compounds are mixed sodium and potassium ion channel blockers and exhibit antiarrhythmic activity in a rat model of ischemia-induced arrhythmias. Structure-activity studies led to the identification of three compounds 5, 18, and 26, which were selected based on their particular in vivo electrophysiological

  描述了制备为潜在抗心律不齐药的一系列2-氨基烷基醚。本发明的化合物是混合的钠和钾离子通道阻滞剂，并且在缺血引起的心律不齐的大鼠模型中表现出抗心律不齐的活性。结构活性研究导致鉴定了三种化合物5、18和26，这是根据它们的特定体内电生理特性选择的，用于两种犬心房颤动（AF）模型的研究。在这两种模型中，这三种化合物均可转化为AF，但仅化合物26被证明具有口服生物利用度。将外消旋物26拆分为其相应的对映体40和41，然后对这些对映体进行生物学测试，结果导致选择（1S，
• Mo‐Based Oxidizers as Powerful Tools for the Synthesis of Thia‐ and Selenaheterocycles
  作者：Peter Franzmann、Sebastian B. Beil、Dieter Schollmeyer、Siegfried R. Waldvogel

  DOI：10.1002/chem.201805938

  日期：2019.2.6

  A highly efficient synthetic protocol for the synthesis of thia‐ and selenaheterocycles has been developed. By employing a MoCl5‐mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide

  已经开发了用于合成噻吩和亚硒杂环的高效合成方案。通过使用MoCl 5介导的分子内脱氢偶联反应，可以分离出多种结构基序，产率最高可达94％。几个不稳定的部分（如卤化物和叔烷基）可以忍受亲电子键的转变。由于使用了二硫化物或二硒化物前体，因此获得了很高的原子效率。
• Catechol carboxylic acids
  申请人：Hoffmann-La Roche Inc.

  公开号：US05025036A1

  公开（公告）日：1991-06-18

  The invention relates to catechol carboxylic acid derivatives of the formula ##STR1## wherein, R.sub.1 is ##STR2## acetyl, hydrogen, hydroxy or alkanoyloxy, R.sub.2 is ##STR3## hydroxy, hydrogen or alkanoyloxy, wherein R is hydrogen, lower alkyl or --(CH.sub.2).sub.n --N--(lower alkyl).sub.2, R.sub.3 is hydrogen, lower alkyl or amino, R.sub.4 is hydrogen, lower alkyl, halogen or amino A is ##STR4## wherein, R.sub.5 is hydrogen or acyl, R.sub.6 is hydrogen, halogen, lower alkyl, aryl or cycloalkyl, and R.sub.7 and R.sub.8, independently, are hydrogen, lower alkyl or halogen, or A is ##STR5## wherein, R.sub.5 is hydrogen or acyl, R.sub.9 is hydrogen, lower alkyl, R.sub.10 is hydrogen, lower alkyl or halogen, R.sub.11 is hydrogen, lower alkyl, cycloalkyl or halogen, m is 0 or 1, n is an integer of 2-10, provided, that no more than one of R.sub.1 or R.sub.2 can be hydroxy, alkanoyloxy or ##STR6## and when R is hydrogen, salts thereof with pharmaceutically acceptable bases or when R is --(CH.sub.2).sub.n --N--(lower alkyl).sub.2, salts thereof with pharmaceutically acceptable acids. The compounds of formula I are useful as agents for the treatment of inflammatory diseases such as arthritis, inflammatory bowel disease such as colitis, cardiovascular diseases such as myocardial ischemia, skin diseases such as psoriasis by topical administration, and bronchopulmonary diseases such as asthma.

  这项发明涉及公式##STR1##的儿茶酚羧酸衍生物，其中，R.sub.1为##STR2##乙酰基，氢，羟基或烷酰氧基，R.sub.2为##STR3##羟基，氢或烷酰氧基，其中R为氢，低烷基或--(CH.sub.2).sub.n --N--(低烷基).sub.2，R.sub.3为氢，低烷基或氨基，R.sub.4为氢，低烷基，卤素或氨基，A为##STR4##其中，R.sub.5为氢或酰基，R.sub.6为氢，卤素，低烷基，芳基或环烷基，而R.sub.7和R.sub.8，独立地，为氢，低烷基或卤素，或A为##STR5##其中，R.sub.5为氢或酰基，R.sub.9为氢，低烷基，R.sub.10为氢，低烷基或卤素，R.sub.11为氢，低烷基，环烷基或卤素，m为0或1，n为2-10的整数，前提是R.sub.1或R.sub.2中不超过一个可以是羟基，烷酰氧基或##STR6##，当R为氢时，其与药学上可接受的碱盐，或当R为--(CH.sub.2).sub.n --N--(低烷基).sub.2时，其与药学上可接受的酸盐。公式I的化合物可用作治疗类风湿性关节炎、炎症性肠病如结肠炎、心血管疾病如心肌缺血、皮肤疾病如牛皮癣经局部给药治疗，以及支气管肺部疾病如哮喘的药物。
• Mechanistic studies of the free-radical fragmentation of monoalkyl diazenes
  作者：Andrew G. Myers、Mohammad Movassaghi、Bin Zheng

  DOI：10.1016/s0040-4039(97)01497-4

  日期：1997.9

  Mechanistic studies of the deoxygenation of primary alcohols by Mitsunobu displacement with o-nitrobenzenesulfonylhydrazine (NBSH) reveal that the monoalkyl diazene intermediates formed in this process are exceedingly good hydrogen-atom donors toward alkyl radicals, exceeding tri-n-butyltin hydride in reactivity. Competition experiments are described wherein the radical intermediates are trapped by intra-

  伯醇的光延由脱氧的机理研究位移ö -nitrobenzenesulfonylhydrazine（NBSH）表明，形成在此过程中，单烷基二氮烯中间体是极其良好的氢原子给体朝向烷基，超过三Ñ在反应-butyltin氢化物。描述了竞争实验，其中自由基中间体被分子内和分子间加成到碳-碳双键，双氧和成自由基的2,2,6,6-四甲基哌啶-N-氧基（TEMPO）上。