1-butyl-2,4-dimethoxybenzene | 54459-33-5

• 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: 1-butyl-2,4-dimethoxybenzene
• 英文别名: 2,4-dimethoxy-n-butylbenzene；1-butyl-2,4-dimethoxy-benzene；1-Butyl-2,4-dimethoxy-benzol；1-n-Butyl-2,4-dimethoxybenzol；Benzene, 1,3-dimethoxy-4-butyl
• CAS: 54459-33-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: ABWZWFPWDXRRFS-UHFFFAOYSA-N

物化性质

• 沸点：
  264 °C(Press: 710 Torr)
• 密度：
  1.006 g/cm3(Temp: 314 °C)
• 保留指数：
  1476

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-butyl-2,4-dimethoxybenzene 在 盐酸 、 正丁基锂 、 氯化亚砜 、 三溴化硼 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 4.0h， 生成 3-Butyl-N-((S)-1-ethyl-pyrrolidin-2-ylmethyl)-2-hydroxy-6-methoxy-benzamide
  参考文献：
  名称：

  Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

  摘要：

  A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20-fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substituent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.

  DOI：

  10.1021/jm00147a025
• 作为产物：
  描述：

  1-[(E)-but-1-enyl]-2,4-dimethoxybenzene 生成 1-butyl-2,4-dimethoxybenzene
  参考文献：
  名称：

  PAULIS, T. DE;KUMAR, YATENDRA;JOHANSSON, L.;RAEMSBY, S.;FLORVALL, L.;HALL+, J. MED. CHEM., 1985, 28, N 9, 1263-1269

  摘要：

  DOI：

文献信息

• Leukotriene B4 receptor antagonists: the LY255283 series of hydroxyacetophenones
  作者：David K. Herron、Theodore Goodson、Nancy G. Bollinger、Dorothy Swanson-Bean、Ian G. Wright、Gilbert S. Staten、Alan R. Thompson、Larry L. Froelich、William T. Jackson

  DOI：10.1021/jm00088a018

  日期：1992.5

  A series of hydroxyacetophenones was prepared for evaluation as leukotriene B4 (LTB4) receptor antagonists, culminating in 1-[5-ethyl-2-hydroxy-4-[[6-methyl-6-(1H-tetrazol-5- yl)heptyl]oxy]phenyl]ethanone (compound 35, LY255283). Using an assay for inhibition of specific [3H]LTB4 binding to human PMN, we found that substitution of a nonpolar substituent in the 5-position was required for activity.

  制备了一系列羟基苯乙酮作为白三烯B4（LTB4）受体拮抗剂进行评估，最终以1- [5-乙基-2-羟基-4-[[6-甲基-6-（1H-四唑-5-基）庚基] [氧基]苯基]乙酮（化合物35，LY255283）。使用抑制特异性[3H] LTB4与人PMN结合的测定方法，我们发现活性需要5位非极性取代基的取代。最佳活性是通过3位氢，2位羟基，1位短链烷基酮以及将4位氧与不饱和末端相连的六碳或八碳链实现的功能。选择在结合试验中IC50为87 nM的化合物35进行进一步的临床前评估。
• Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated <i>via</i> C(sp³)–H activation
  作者：Zhuo Wu、Hang Jiang、Yanghui Zhang

  DOI：10.1039/d1sc01731d

  日期：——

  Transition-metal-catalyzed cross-electrophile C(sp2)–(sp3) coupling and C–H alkylation reactions represent two efficient methods for the incorporation of an alkyl group into aromatic rings. Herein, we report a Pd-catalyzed cascade cross-electrophile coupling and C–H alkylation reaction of 2-iodo-alkoxylarenes with alkyl chlorides. Methoxy and benzyloxy groups, which are ubiquitous functional groups

  过渡金属催化的交叉亲电试剂C（sp 2）–（sp 3）偶联和C–H烷基化反应代表了将烷基结合到芳环中的两种有效方法。在这里，我们报道了2-碘-烷氧基芳烃与烷基氯的钯催化级联交叉亲电子偶联和CH烷基化反应。甲氧基和苄氧基基团是普遍存在的官能团和常见的保护基团，被用作通过一级或二级C（sp 3）–H活化的关键介质。该反应为合成烷基化的苯酚衍生物提供了一种新颖而便捷的途径，烷基化的苯酚衍生物广泛存在于生物活性化合物和有机功能材料中。
• 15-PGDH INHIBITOR
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP3922247A1

  公开（公告）日：2021-12-15

  [Problem] To provide a compound having a 15-PGDH inhibitory effect. [Solution] A compound represented by general formula (1) or a pharmacologically acceptable salt thereof.

  问题 提供一种具有 15-PGDH 抑制作用的化合物。 [解决方案］ 一种由通式（1）代表的化合物或其药理学上可接受的盐。
• Irani; Phalnikar; Nargund, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1948, vol. 16/5 A, p. 41
  作者：Irani、Phalnikar、Nargund

  DOI：——

  日期：——
• Anti-inflammatory agents
  申请人：ELI LILLY AND COMPANY

  公开号：EP0276065B1

  公开（公告）日：1990-06-06