3-hydroxy-5-methoxybenzonitrile | 124993-53-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-5-methoxybenzonitrile
• 英文别名: 3-cyano-5-methoxy phenol；3-CYANO-5-METHOXYPHENOL
• CAS: 124993-53-9
• 化学式: C₈H₇NO₂
• mdl: MFCD11520902
• 分子量: 149.149
• InChiKey: QBXVEVNURVZFTM-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  298.0±30.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-methoxybenzonitrile 在 镍 氨 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.67h， 以100%的产率得到3-hydroxy-5-methoxybenzylamine
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region"

  摘要：

  A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring Ca-45(2+) uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic ''A-region'' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.

  DOI：

  10.1021/jm00068a014
• 作为产物：
  描述：

  3,5-二甲氧基苯腈 在 2-二乙氨基乙硫醇盐酸盐 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以80%的产率得到3-hydroxy-5-methoxybenzonitrile
  参考文献：
  名称：

  2-（二乙氨基）乙硫醇，一种无臭的芳香甲基醚脱保护新试剂

  摘要：

  报道了一种用于芳族甲基醚的脱保护的新试剂2-（二乙基氨基）乙硫醇。这种化合物以其HCl盐的形式商购可得，可在多种底物上以高至极好的收率提供相应的酚。与使用更常见的硫醇（如乙硫醇）相比，此方法的明显优势在于，通过用稀酸淬灭，可以轻松地将脱保护剂和副产物2-（二乙氨基）乙基甲基硫化物萃取到水相中，从而实现基本上无味的处理。

  DOI：

  10.1021/jo0611059

文献信息

• [EN] FUNGICIDES<br/>[FR] FONGICIDES
  申请人：SYNGENTA LTD

  公开号：WO2004047537A1

  公开（公告）日：2004-06-10

  The use as a plant fungicide of a compound of the general formula (I): wherein X and Y are both chloro, bromo or methyl or X is methoxy and Y is cyano; R1 is ethyl or n-propyl and R2 is methyl or ethyl. The compounds (1), other than those where X and Y are both chloro or methyl and R1 is ethyl, are novel.

  将通式（I）的化合物用作植物真菌剂，其中X和Y均为氯、溴或甲基，或者X为甲氧基，Y为氰基；R1为乙基或正丙基，R2为甲基或乙基。除了X和Y均为氯或甲基且R1为乙基的化合物（1）之外，其余化合物均为新颖的。
• Non-nucleoside reverse transcriptase inhibitors
  申请人：Sweeney Zachary Kevin

  公开号：US20080020981A1

  公开（公告）日：2008-01-24

  The present invention provides for compounds useful for treating an HIV infection, or preventing an HIV infection, or treating AIDS or ARC. The compounds of the invention are of formula I wherein R 1 , R 2 , R 3 , R 4 , X 1 and X 2 are as herein defined. Also disclosed in the present invention are methods of treating an HIV infection with compounds defined herein and pharmaceutical compositions containing said compounds.

  本发明提供了用于治疗HIV感染、预防HIV感染、治疗AIDS或ARC的化合物。本发明的化合物具有以下式I的结构，其中R1、R2、R3、R4、X1和X2如本文所定义。本发明还公开了使用本文所定义的化合物治疗HIV感染的方法以及含有该化合物的药物组合物。
• HETEROCYCLIC ANTIVIRAL COMPOUNDS
  申请人：Billedeau Roland Joseph

  公开号：US20090170856A1

  公开（公告）日：2009-07-02

  Compounds of formula I, wherein R 1 , R 2 , R 3 , X 1 , X 2 and Ar, are as defined herein or pharmaceutically acceptable salts thereof, inhibit HIV-1 reverse transcriptase and afford a method for prevention and treatment of HIV-1 infections and the treatment of AIDS and/or ARC. The present invention also relates to compositions containing compounds of formula I useful for the prevention and treatment of HIV- 1 infections and the treatment of AIDS and/or ARC.

  式I化合物，其中R1、R2、R3、X1、X2和Ar如本文所定义，或其药学上可接受的盐，抑制HIV-1逆转录酶，并提供预防和治疗HIV-1感染以及治疗艾滋病和/或艾滋病相关复合征（ARC）的方法。本发明还涉及含有式I化合物的组合物，这些组合物对于预防和治疗HIV-1感染以及治疗艾滋病和/或ARC是有用的。
• Development of a novel series of (2-quinolinylmethoxy)phenyl-containing compounds as high-affinity leukotriene D4 receptor antagonists. 2. Effects of an additional phenyl ring on receptor affinity
  作者：Fu Chih Huang、Robert A. Galemmo、William H. Johnson、Gregory B. Poli、Matthew M. Morrissette、James J. Mencel、James D. Warus、Henry F. Campbell、George W. Nuss

  DOI：10.1021/jm00166a017

  日期：1990.4

  on biological activity are discussed. Many of these compounds have high affinity to the sulfidopeptide leukotriene D4 receptors with Ki values ranging between 2 and 20 nM and are orally active. Compound 27 [RG 12525, 5-[[2-[[4-(2-quinolinylmethoxy)phenoxy]- methyl]phenyl]methyl]-1H-tetrazole] represents the best combination of in vitro and in vivo biological activity in this series and has been selected

  该系列报道描述了含有（2-喹啉基甲氧基）苯基部分的肽白三烯的口服活性，高效，特异性拮抗剂的开发。本文报道的化合物包含一个额外的苯环，该苯环显着提高了受体亲和力。讨论了两个苯环之间的键变化以及酸性官能团的取向对生物活性的影响。这些化合物中的许多化合物对磺肽白三烯D4受体具有高亲和力，Ki值在2至20 nM之间，并且具有口服活性。化合物27 [RG 12525，
• [EN] N-ALKYNYL-2- (SUBSTITUTED PHENOXY) ALKYLAMIDES AND THEIR USE AS FUNGICIDES<br/>[FR] N-ALKYNYL-2-ALKYLAMIDES (PHENOXY SUBSTITUES) ET LEUR UTILISATION EN TANT QUE FONGICIDES
  申请人：SYNGENTA LTD

  公开号：WO2004048316A1

  公开（公告）日：2004-06-10

  Fungicidal compounds of the general formula (1) wherein X, Y, Z, R1, R2, R3, R4 and R5 have the definitions given in claim 1.

  通式（1）中的杀真菌化合物，其中X、Y、Z、R1、R2、R3、R4和R5的定义如权利要求书中所述。