2,3-二氯-4-甲氧基苯酚 | 39542-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,3-二氯-4-甲氧基苯酚
• 英文名称: 2,3-dichloro-4-methoxyphenol
• CAS: 39542-65-9
• 化学式: C₇H₆Cl₂O₂
• 分子量: 193.029
• InChiKey: WIISWCJUGKFBMI-UHFFFAOYSA-N

物化性质

• 沸点：
  277.7±35.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-二氯-4-甲氧基苯酚 在 镍 盐酸 、 硫酸 、 氢溴酸 、 氢气 、 sodium hydride 、 potassium carbonate 、 sodium nitrite 作用下， 以 溶剂黄146 、 丁酮 为溶剂， 反应 39.75h， 生成 <2,3-dichloro-4-<4-hydroxy-3-<(2-chloroacetyl)aminomethyl>phenoxy>phenoxy>acetic acid
  参考文献：
  名称：

  [(Aminomethyl)aryloxy]acetic acid esters. A new class of high-ceiling diuretics. 3. Variation in the bridge between the aromatic rings to complete mapping of the receptor

  摘要：

  Continued structural evaluation of the [(aminomethyl)aryloxy]acetic ester diuretics has produced a series of compounds in which the functional group that bridges the two aromatic rings has been varied. Diuretic screening of these analogues in rats indicates that the keto group can be effectively replaced with an ether or thio ether function with a slight increase in potency, whereas the methylene and sulfoxide linking groups lead to diminished saluretic potency. Replacement with either -SO2-, -COCO-, -CH2O-, -CONH- or direct bond results in a loss of activity. Although the series was designed according to QSAR criteria, the traditional linear free-energy properties of these compounds do not correlate with diuretic potency. However, conformational analysis of the series by potential energy calculations indicates that all active compounds have an accessible conformation that matches the bridge atom-carboxylate distance of the very potent dihydrobenzofuran analogue 56. Conformational calculations of several compounds in which the aminomethyl group was varied suggests that the active conformation is probably a low-energy conformation. Consideration of rotation about the bridge could not distinguish between two possible orientations of the aminomethyl ring in the active conformation. However, there is a quantitative negative linear correlation between diuretic potency and the protrusion into space of the group that bridges the two aromatic rings.

  DOI：

  10.1021/jm00379a016
• 作为产物：
  描述：

  5,6-dichlorocyclohex-2-ene-1,4-dione 在 sodium hydroxide 、 硫酸 、 溶剂黄146 作用下， 生成 2,3-二氯-4-甲氧基苯酚
  参考文献：
  名称：

  Dallacker,F.; Van Wersch,J., Chemische Berichte, 1972, vol. 105, p. 3301 - 3305

  摘要：

  DOI：

文献信息

• 一种4-烷氧基苯酚类化合物的合成方法
  申请人：新乡医学院

  公开号：CN113443970B

  公开（公告）日：2023-04-07

  本发明公开了一种4‑烷氧基苯酚类化合物的合成方法，属有机化学合成领域。方法如下：向密封管中加入芳基烷基醚类化合物、催化剂二聚醋酸铑和氧化剂碘苯二乙酯，然后加入溶剂三氟乙酸酐，加热反应制得4‑烷氧基苯酚类化合物。本发明实现了芳基烷基醚类化合物的高区域选择性直接羟基化，不仅底物适用范围广，产率高，而且放大反应后活性未出现明显衰弱，仍获得较高的收率。具有很好的实用性和工业应用前景。
• Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N′-dimethylhydrazine dihydrochloride
  作者：Zhiwei Yin、Jinzhu Zhang、Jing Wu、Riana Green、Sihan Li、Shengping Zheng

  DOI：10.1039/c4ob00391h

  日期：——

  An unexpected nucleophilic chlorination of a quinone monoketal while carrying out a pyrazolidine synthesis has led to a general preparation of multisubstituted phenols. The products are obtained in good to high yields under mild conditions. The bridged pyrazolidines that were the original targets are obtained in the presence of a protic solvent.

  在进行吡唑啉合成时，发生了一次意外的亲核氯化反应，导致了对醌单缩酮的多取代苯酚的一般制备。在温和条件下，产物以良好至高产率获得。在质子溶剂存在下，原本的桥连吡唑啉目标化合物也能得到。
• <i>para</i>-Selective hydroxylation of alkyl aryl ethers
  作者：Runqing Zhu、Qianqian Sun、Jing Li、Luohao Li、Qinghe Gao、Yakun Wang、Lizhen Fang

  DOI：10.1039/d1cc06210g

  日期：——

  para-Selective hydroxylation of alkyl aryl ethers is established, which proceeds with a ruthenium(II) catalyst, hypervalent iodine(III) and trifluoroacetic anhydride via a radical mechanism. This protocol tolerates a wide scope of substrates and provides a facile and efficient method for preparing clinical drugs monobenzone and pramocaine on a gram scale.

  建立了烷基芳基醚的对位选择性羟基化反应，该反应在钌（II）催化剂、高价碘（III）和三氟乙酸酐的作用下通过自由基机制进行。该协议可耐受广泛的底物，并提供了一种简便有效的方法来制备克级临床药物莫诺苯宗和普罗卡因。
• Diphenyl ether, diphenyl thioether and diphenyl methane phenol mannich
  申请人：Abbott Laboratories

  公开号：US04389416A1

  公开（公告）日：1983-06-21

  Described are compounds of the formula ##STR1## wherein R is hydrogen, loweralkyl, aminomethyl or halo; R.sub.1 is carboxy, carboxyloweralkyl, aminocarbonyl, hydroxymethyl, anilinomethyl, or aminomethyl; A is oxygen, CH.sub.2, Sulfur or a single bond; X is oxygen, CH.sub.2, sulfur or sulfoxide; and Y is hydrogen, loweralkyl or halo and may be the same or different, and pharmaceutically acceptable salts thereof. The compounds are effective as diuretic agents.

  描述的是化合物的公式 ##STR1## 其中 R 是氢、较低的烷基、氨甲基或卤素；R.sub.1 是羧基、羧基较低烷基、氨基甲酰、羟甲基、苯胺甲基或氨基甲基；A 是氧、CH.sub.2、硫或单键；X 是氧、CH.sub.2、硫或亚硫酰氧；Y 是氢、较低烷基或卤素，可以相同也可以不同，以及其药学上可接受的盐。这些化合物作为利尿剂具有有效性。
• Dimethylaminomethylation of phenols and α-naphthols
  作者：A. N. Grinev、S. A. Zotova

  DOI：10.1007/bf00761182

  日期：1974.10