3-hydroxy-4-methoxyphenylacetonitrile | 4468-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-4-methoxyphenylacetonitrile
• 英文别名: 3-hydroxy-4-methoxybenzyl cyanide；3-hydroxy-4-methoxy-benzeneacetonitrile；4-Cyanomethyl-2-hydroxy-1-methoxybenzene；3-Hydroxy-4-methoxyphenylacetonitril；3-Hydroxy-4-methoxybenzylcyanid；2-(3-Hydroxy-4-methoxyphenyl)acetonitrile
• CAS: 4468-58-0
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: YAIONKMWQNEDJU-UHFFFAOYSA-N

物化性质

• 沸点：
  332.1±27.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxyphenylacetonitrile 在 sodium hydroxide 、 sodium tetrahydroborate 、 溴 、 三氯氧磷 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.67h， 生成 (+/-)-6'-Bromo-N-norreticuline
  参考文献：
  名称：

  以吗啡合成为目标的研究，IV：一种从均四腈中提取 N-去甲网状番荔枝碱衍生物的新方法

  摘要：

  用路易斯酸部分去甲基化高过四腈 (3a) 得到异构单酚 3b 和 3c 的混合物。异构体的分离为 N-去甲网状番荔枝碱 (1a) 及其 6'- 卤素衍生物 1b、c 提供了一种新方法。

  DOI：

  10.1002/ardp.19813141203
• 作为产物：
  描述：

  5-formyl-2-methoxyphenyl 4-methylbenzenesulfonate 在 氢氧化钾 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 生成 3-hydroxy-4-methoxyphenylacetonitrile
  参考文献：
  名称：

  光化学合成7,8-双加氧异喹啉生物碱

  摘要：

  报道了一种基于由3-羟基-4-甲氧基苯基乙腈衍生的酯的弗里斯-弗里斯重排而合成7,8-二加氧四氢异喹啉碱生物碱的新方法。该方法适用于生物碱Arizonine和1 -2-berbine生物碱的1-苄基四氢异喹啉碱的合成。

  DOI：

  10.1016/0040-4039(94)02448-k

文献信息

• Oxidation of Methoxy- and/or Methyl-Substituted Benzenes and Naphthalenes to Quinones and Phenols by H₂O₂in HCOOH
  作者：Hideo Orita、Masao Shimizu、Takashi Hayakawa、Katsuomi Takehira

  DOI：10.1246/bcsj.62.1652

  日期：1989.5

  The oxidation of a number of arenes (methoxybenzenes, methylbenzenes, and naphthalenes) to quinones and phenols by H2O2 in HCOOH has been examined. Methoxybenzenes were much more easily oxidized to p-benzoquinones than methylbenzenes (e.g., 1,3,5-trimethoxybenzene was oxidized to 2,6-dimethoxy-p-benzoquinone in a 75% yield and 1,2,4-trimethylbenzene to 2,3,5-trimethyl-p-benzoquinone in a 16% yield)

  已经研究了在 HCOOH 中通过 H2O2 将许多芳烃（甲氧基苯、甲苯和萘）氧化为醌和苯酚。甲氧基苯比甲基苯更容易氧化成对苯醌（例如，1,3,5-三甲氧基苯以 75% 的产率氧化成 2,6-二甲氧基-对苯醌，1,2,4-三甲苯氧化成 2， 3,5-三甲基-对苯醌，产率为 16%）。吸电子取代基，如硝基、氰基和氯基团，降低了反应物的转化率，并将产物的选择性从醌类变为酚类。甲氧基苄腈以中等产率氧化成相应的酚类（例如，2,6-二甲氧基苄腈以39%的产率和64%的选择性氧化成3-羟基-2,6-二甲氧基苄腈）。
• The Palladium-Catalyzed Preparation of Condensed Tetracyclic Heterocycles and their Application to the Synthesis of <i>rac</i>-Mangochinine
  作者：András Kotschy、Zoltán Vincze、A. Bíró、Márton Csékei、Géza Timári

  DOI：10.1055/s-2006-926410

  日期：2006.4

  Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine.

  通过Bischler-Napieralsky反应制备的二氢异喹啉衍生物及其类似物被转化为其吲哚融合衍生物。研究了通过这些化合物的互变酮胺形式进行的钯催化反应的范围和限制，并将该过程扩展到外消旋芒果喹啉的制备。
• Bhandari, Prabha; Crombie, Leslie; Daniels, Peter, Journal of the Chemical Society. Perkin transactions I, 1992, # 7, p. 839 - 850
  作者：Bhandari, Prabha、Crombie, Leslie、Daniels, Peter、Holden, Ian、Bruggen, Nicholas Van、Whiting, Donald A.

  DOI：——

  日期：——
• Synthesis of new dipyrrolo- and furopyrrolopyrazinones related to tripentones and their biological evaluation as potential kinases (CDKs1–5, GSK-3) inhibitors
  作者：Christophe Rochais、Nghia Vu Duc、Elodie Lescot、Jana Sopkova-de Oliveira Santos、Ronan Bureau、Laurent Meijer、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2008.05.011

  日期：2009.2

  We herein describe the synthesis of novel dipyrrolo- and furopyrrolopyrazinones related to highly cytotoxic tripentones and to their oximes. The synthetic pathway involved in particular a Curtius rearrangement and a subsequent cyclisation into the title pyrazinones. The biological evaluation towards various cyclin-dependent kinases (CDKs1-5, GSK-3) highlighted a weak inhibitory activity for the oximes whose SAR was studied by a molecular modeling study. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Syntheses of dopaminergic 1-cyclohexylmethyl-7,8-dioxygenated tetrahydroisoquinolines by selective heterogeneous tandem hydrogenation
  作者：Inmaculada Andreu、Nuria Cabedo、Gregorio Torres、Abdeslam Chagraoui、M Carmen Ramı́rez de Arellano、Salvador Gil、Almudena Bermejo、Marı́a Valpuesta、Philippe Protais、Diego Cortes

  DOI：10.1016/s0040-4020(02)01403-5

  日期：2002.12

  We describe the preparation in a 'one-pot' sequence I-cyclohexylmethyl 7,8-dioxygenated tetrahydroisoquinoline, substituted and unsubstituted in the C ring by application of the Photo-Fries transposition, followed by a tandem reduction-cyclization and further reduction. Indeed, we have accomplished for the first time regioselective hydrogenation of the benzylic ring of the tetrahydroisoquinoline systems. All I-cyclohexylmethyl THIQ synthesized were able to displace D-2 dopamine receptor from its specific binding site in rat striatal membranes, while the N-methylated derivatives showed also affinity for D-1 dopamine receptors. (C) 2002 Published by Elsevier Science Ltd.