2,4-bis(chloromethyl)-1-methoxybenzene | 25445-34-5

• 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: 2,4-bis(chloromethyl)-1-methoxybenzene
• 英文别名: 2,4-Bis-chlormethyl-anisol；1-methoxy-2,4-bis(chloromethyl)benzene；Anisole, 2,4-bis(chloromethyl)-
• CAS: 25445-34-5
• 化学式: C₉H₁₀Cl₂O
• 分子量: 205.084
• InChiKey: ZBQXEAIGIXABOB-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于氯仿-d；二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-bis(chloromethyl)-1-methoxybenzene 在 potassium permanganate 、 氯化亚砜 作用下， 生成 4-甲氧基异PHTHALOYL 二氯化物
  参考文献：
  名称：

  邻苯二甲酸4-甲氧基二芳基酯的设计，合成及生物学评价

  摘要：

  使用等排构想设计和合成了一系列的4-甲氧基二苯基间苯二甲酸酯，它们是吡咯酰胺的同构类似物。这些新类似物的结构通过所有光谱学方法进行了表征，包括1 H NMR，13 C NMR和MS光谱。这些化合物的体外抗血小板聚集活性通过使用Born检验方法进行了研究。在针对ADP和胶原诱导剂测试的19种化合物中，发现其中的6种（P216-P219和P220-P221）在体外的抗血小板凝集活性高于Picotamide。尤其是，带有硝基氧基的化合物P220的最高活性为72.1％（由胶原蛋白诱导）和72.5％（由ADP诱导），IC50值为0.30μM/ L，由ADP（1.3μM/ L）和LD50> 2500 mg / kg，可能具有双重作用机制。所述化合物对L929细胞系的细胞毒性活性的评估表明，没有一种化合物具有明显的细胞毒性。通过仔细分析体外活性数据，初步推导了这些化合物的SAR。这项研究的结果表明，4-

  DOI：

  10.1007/s00044-017-2075-7
• 作为产物：
  描述：

  苯酚 在 盐酸 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 苯 为溶剂， 生成 2,4-bis(chloromethyl)-1-methoxybenzene
  参考文献：
  名称：

  Synthesis and in vitro activities on anti-platelet aggregation of 4-methoxyisophthalamides

  摘要：

  A series of 4-methoxyisophthalamides (1d-1w) were designed and synthesized and their chemical structures were confirmed by IR, MS, H-1-NMR, and C-13-NMR. The in vitro on anti-platelet aggregation activities of these compounds were assessed by using Born method. Compounds with higher activities were selected to continue research via Cell Counting Kit-8 (CCK-8) assays of their cytotoxicities. Biological screening results revealed four compounds 1h, 1i, 1q, and 1v exhibited higher activities than the control drugs on against the platelet aggregation induced by adenosine triphosphate (ADP). Moreover, compounds 1p and 1q exhibited higher in vitro activities than picotamide induced by collagen at the concentration of 1.3 mu M. Compound 1p also possessed anti-platelet aggregation activity superior to the control drug picotamide induced by arachidonic acid (AA) at the concentration of 1.3 mu M. At the same time, the result of cytotoxicities exhibited that none of the compounds have significant cytotoxicities. Therefore, 4-methoxyisophthalamides are potential to become novel anti-platelet drugs with high activities and minimum toxicities.

  DOI：

  10.1007/s00044-018-2207-8

文献信息

• AN EXPERIMENTAL AND THEORETICAL STUDY ON IMIDAZOLIUM-BASED IONIC LIQUID PROMOTED CHLOROMETHYLATION OF AROMATIC HYDROCARBONS
  作者：YUN WANG、YANLI XI

  DOI：10.4067/s0717-97072013000400063

  日期：——

  accordance with the experimental outcomes. Keywords: Ionic liquid, Chloromethylation, Aromatic hydrocarbons, DFT, Solvent effects 1. INTRODUCTION Chloromethyl substituted aromatic hydrocarbons are promising key intermediates because of easy transformation to many chemicals such as fine-chemicals, pharmaceuticals, and polymers. The chloromethylation of aromatic hydrocarbons has been documented in previous papers

  摘要使用可重复使用的咪唑基离子液体作为促进剂可有效地进行芳烃的氯甲基化。在离子液体中观察到的显着特征是温和的反应条件，提高的速率，提高的产率，离子液体的可回收性以及与常规有机溶剂不同的试剂反应性。离子液体在随后的三个运行中循环使用，而活性没有降低。此外，使用高斯98程序套件的计算结果与实验结果非常吻合。关键字：离子液体氯甲基化芳烃DFT溶剂效应1.简介氯甲基取代的芳烃是有希望的关键中间体，因为它易于转化为许多化学品，例如精细化学品，药品和聚合物。先前文献已记录了芳烃的氯甲基化。[1-7]芳族烃与作为甲醛前体的盐酸和三恶烷或多聚甲醛反应有时会得到没有催化剂的氯甲基化产物。
• Pd-Catalyzed Cross-Coupling of <i>Sb</i>-Aryl Stibines with Halogenomethyl Arenes to Give Unsymmetirc Diarylmethanes
  作者：Dejiang Zhang、Zhi Xu、Ting Tang、Liyuan Le、Cairong Wang、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.2c00879

  日期：2022.5.6

  Herein, we describe a general method for the synthesis of unsymmetric diarylmethanes from (hetero)aryl methyl halides and Sb-aryl stibines. This protocol shows a broad substrate scope and a good functional group tolerance. Drug molecules, including beclobrate 3al and bifemelane 3as, and drug derivatives, including celecoxib 3p, ibuprofen 3ao, and probenecid 3ap, were efficiently synthesized on a gram

  在此，我们描述了一种由（杂）芳基甲基卤化物和Sb-芳基锑合成不对称二芳基甲烷的通用方法。该协议显示了广泛的底物范围和良好的功能组耐受性。药物分子，包括 beclobrate 3al和bifemelane 3as，以及药物衍生物，包括 celecoxib 3p、布洛芬3ao和丙磺舒3ap，以克级高效合成。在对照实验结果的基础上提出了可能的机理。
• Method for making intermediates useful in synthesis of retroviral protease inhibitors
  申请人：G.D. SEARLE & CO.

  公开号：EP0855388A2

  公开（公告）日：1998-07-29

  A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a cyanohydrin from a chiral alpha amino aldehyde.

  本文介绍了一种易于大规模制备羟乙基脲类手性 HIV 蛋白酶抑制剂的中间体合成方法。该方法包括从手性α-氨基醛中形成氰醇。
• Method of preparing intermediates useful in synthesis of retroviral protease inhibitors
  申请人：G.D. Searle & Co.

  公开号：US20020161234A1

  公开（公告）日：2002-10-31

  A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.

  本文介绍了一种易于大规模制备羟乙基脲类手性 HIV 蛋白酶抑制剂的中间体合成方法。该方法包括利用手性α-氨基醛形成非对映选择性环氧化物。
• Method for preparing intermediates useful in synthesis of retroviral protease inhibitors
  申请人：G.D. Searle & Co.

  公开号：US20030225285A1

  公开（公告）日：2003-12-04

  A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide from a chiral alpha amino aldehyde.

  本文介绍了一种易于大规模制备羟乙基脲类手性 HIV 蛋白酶抑制剂的中间体合成方法。该方法包括利用手性α-氨基醛形成非对映选择性环氧化物。

表征谱图