2-allyl-3-hydroxy-4-methoxy-benzonitrile | 106662-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-allyl-3-hydroxy-4-methoxy-benzonitrile
• 英文别名: 3-Hydroxy-4-methoxy-2-prop-2-enylbenzonitrile；3-hydroxy-4-methoxy-2-prop-2-enylbenzonitrile
• CAS: 106662-36-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: LAPARXCSFOJJBT-UHFFFAOYSA-N

物化性质

• 沸点：
  322.5±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2-allyl-3-hydroxy-4-methoxy-benzonitrile 在 盐酸 、 sodium hydroxide 、 氢溴酸 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 158.0h， 生成 3,4-dihydro-8-ethoxycarbonyloxy-5-formyl-3-hydroxy-2H-1-benzopyran
  参考文献：
  名称：

  Syntheses of ring-hydroxylated nipradilols and their denitro derivatives.

  摘要：

  尼普拉洛尔（NIP），3,4-二氢-8-(2-羟基-3-异丙氨基)丙氧基-3-硝氧基-2H-1-苯并吡喃，在人类和犬类中被广泛代谢。为了鉴定环羟基代谢物，我们合成了顺式和反式4-羟基、5-羟基-NIP及其脱硝衍生物和7-羟基-脱硝-NIP。根据其光谱判断，反式4-羟基-和5-羟基-NIP及其脱硝衍生物对应于分离得到的环羟基代谢物。此外，在麻醉的自发性高血压大鼠中的药理学研究表明，硝氧基衍生物引起了短暂的降压反应，而硝氧基衍生物和脱硝衍生物则导致了持久的心动过缓。

  DOI：

  10.1248/cpb.34.2024
• 作为产物：
  描述：

  3-(allyloxy)-4-methoxybenzaldehyde oxime 在 苯酐 作用下， 反应 2.08h， 生成 2-allyl-3-hydroxy-4-methoxy-benzonitrile
  参考文献：
  名称：

  A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN

  摘要：

  A novel synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones is described. o-Oxiranylmethylbenzonitriles, prepared from isovanillin via five synthetic steps, were treated with NaCN/tetra-n-butylammonium bromide (TBAB) to yield 3,4-dihydroisoquinolin-1(2H)-ones in good yields. This one pot reaction demonstrates the novel and chemoselective nature of ring-opening of epoxide by cyanide to generate an iminoisochroman ring via cyclization, again ring-opening by cyanide to generate a Michael acceptor and a donor, and ring re-cyclization through an intramolecular conjugate addition. The detailed mechanism is also rationally proposed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.023

文献信息

• t BuO2H/Cu(acac)2-Mediated Intramolecular Oxidative Lactonization of o-Allyl Arylaldehydes: Synthesis of 1-Oxoisochromans
  作者：Meng-Yang Chang、Kai-Xiang Lai、Kuan-Ting Chen

  DOI：10.1055/s-0040-1706469

  日期：2021.2

  Abstract A concise route for the t BuO2H/Cu(acac)2-mediated synthesis of 1-oxoisochromans is described. This includes: (i) oxidation of oxygenated o-allyl arylaldehydes and (ii) sequential intramolecular lactonization of the resulting olefin-containing benzoic acids. A plausible mechanism is proposed and discussed. Publication History Received: 14 July 2020 Accepted after revision: 14 August 2020 Publication

  摘要 描述了由t BuO 2 H / Cu（acac）2介导的1-氧代异色满的合成的简明路线。这包括：（i）氧化的邻烯丙基芳基醛的氧化和（ii）所得的含烯烃的苯甲酸的分子内内酯的顺序内酯化。提出并讨论了一种可行的机制。 出版历史 收到：2020年7月14日 修订后接受：2020年8月14日 发布日期： 2020年9月29日（在线） ©2020年。Thieme。版权所有 Georg Thieme Verlag KGRüdigerstraße14，70469斯图加特，德国
• Syntheses of ring-hydroxylated nipradilols and their denitro derivatives.
  作者：TOSHIHIRO AKASHI、KIYOSHI KAWAMURA、MASAMI SHIRATSUCHI、HIROSHI ISHIHAMA

  DOI：10.1248/cpb.34.2024

  日期：——

  Nipradilol (NIP), 3, 4-dihydro-8-(2-hydroxy-3-isopropylamino)propoxy-3-nitroxy-2H-1-benzopyran, is extensively metabolized in man and dogs. In order to identify the ring-hydroxylated metabolites we have synthesized cis- and trans-4-hydroxy-, and 5-hydroxy-NIP, their denitro derivatives and 7-hydroxy-denitro-NIP. As judged from their spectra, trans-4-hydroxy- and 5-hydroxy-NIP and their denitro derivatives corresponded to the isolated ring-hydroxylated metabolites. Moreover, a pharmacological study in anesthetized spontaneously hypertensive rat showed that the nitroxy derivatives caused a transient hypotensive response, and both the nitroxy derivatives and the denitro derivatives caused long-lasting bradycardia.

  尼普拉洛尔（NIP），3,4-二氢-8-(2-羟基-3-异丙氨基)丙氧基-3-硝氧基-2H-1-苯并吡喃，在人类和犬类中被广泛代谢。为了鉴定环羟基代谢物，我们合成了顺式和反式4-羟基、5-羟基-NIP及其脱硝衍生物和7-羟基-脱硝-NIP。根据其光谱判断，反式4-羟基-和5-羟基-NIP及其脱硝衍生物对应于分离得到的环羟基代谢物。此外，在麻醉的自发性高血压大鼠中的药理学研究表明，硝氧基衍生物引起了短暂的降压反应，而硝氧基衍生物和脱硝衍生物则导致了持久的心动过缓。
• A novel and chemoselective synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones from o-oxiranylmethylbenzonitrile intermediates and TBAB/NaCN
  作者：Po-Yuan Chen、Hsing-Ming Chen、Michael Y. Chiang、You-Feng Wang、Sie-Rong Li、Tzu-Pin Wang、Eng-Chi Wang

  DOI：10.1016/j.tet.2012.02.023

  日期：2012.4

  A novel synthesis of substituted 3,4-dihydroisoquinolin-1(2H)-ones is described. o-Oxiranylmethylbenzonitriles, prepared from isovanillin via five synthetic steps, were treated with NaCN/tetra-n-butylammonium bromide (TBAB) to yield 3,4-dihydroisoquinolin-1(2H)-ones in good yields. This one pot reaction demonstrates the novel and chemoselective nature of ring-opening of epoxide by cyanide to generate an iminoisochroman ring via cyclization, again ring-opening by cyanide to generate a Michael acceptor and a donor, and ring re-cyclization through an intramolecular conjugate addition. The detailed mechanism is also rationally proposed. (C) 2012 Elsevier Ltd. All rights reserved.