(E)-3-(2-hydroxyphenyl)prop-2-enenitrile | 42224-54-4

• 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: (E)-3-(2-hydroxyphenyl)prop-2-enenitrile
• 英文别名: trans-3-(2-hydroxyphenyl)acrylonitrile；3-(2-hydroxyphenyl)-(E)-acrylonitrile；(E)-3-(2-hydroxyphenyl)acrylonitrile；2-hydroxy-trans-cinnamonitrile；2-Hydroxy-trans-cinnamonitril；2-Hydroxy-trans-cinnamonitri；cis-Hydroxycinnamonitrile
• CAS: 42224-54-4
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: XHKGWWGGZWOIEG-HWKANZROSA-N

物化性质

• 沸点：
  315.3±17.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-hydroxyphenyl)prop-2-enenitrile 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 74.0h， 生成
  参考文献：
  名称：

  β-肾上腺素能阻断剂。21.苏-1-（芳氧基）-3-（烷基氨基）丁-2-醇。

  摘要：

  讨论了一系列的threo-1-（芳氧基）-3-（烷基氨基）丁烷-2-醇的合成与构效关系。这些化合物是比相应的1-（芳氧基）-3-（烷基氨基）丙烷-2-醇弱的β-肾上腺素受体拮抗剂。呈现的数据表明，与芳基乙醇胺系列不同，碳原子α上的烷基取代为氧丙醇胺侧链上的氨基官能团并不一定导致增强的血管（β2）选择性。

  DOI：

  10.1021/jm00143a020
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 乙醚 作用下， 生成 (E)-3-(2-hydroxyphenyl)prop-2-enenitrile
  参考文献：
  名称：

  Houben; Pfankuch, Chemische Berichte, 1926, vol. 59, p. 1601

  摘要：

  DOI：

文献信息

• Late‐Stage Direct <i>o</i> ‐Alkenylation of Phenols by Pd ^II ‐Catalyzed C−H Functionalization
  作者：Yandong Dou、Kenry、Jiang Liu、Jianze Jiang、Qing Zhu

  DOI：10.1002/chem.201900530

  日期：2019.5.17

  phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C−H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under

  通过Pd II催化的直接C-H官能化已开发出未保护的酚的o-烯基化。这项工作以酚基团为导向基团，并实现了酚的位点选择性C-H键官能化，从而在60°C时以中等至极好的收率获得了相应的产品。该反应的优点包括使用苯酚作为指导基团进行前所未有的CH官能化，区域选择性高，底物范围广，反应条件温和且效率高。据我们所知，这是利用酚羟基作为指导基团对未保护的酚进行区域选择性CH烯基化的第一个例子。未保护的酪氨酸的烯基化和分子内环化也可以在该催化体系下以高收率成功进行。此外，
• One‐Pot Wittig Reactions in Aqueous Media: A Rapid and Environmentally Benign Synthesis of α,β‐Unsaturated Carboxylic Esters and Nitriles
  作者：Jinlong Wu、Congyong Yue

  DOI：10.1080/00397910600773684

  日期：2006.10

  Abstract One‐pot Wittig reactions of ethyl bromoacetate and bromoacetonitrile with aldehydes in the presence of PPh3 and LiOH in water were investigated. Most of the olefination reactions completed within 5–120 min in refluxing water containing 1.2 M LiCl to afford the olefin products in 71–97% yields with 100:0–55:45 ratios of E:Z isomers.

  摘要 研究了溴乙酸乙酯和溴乙腈与醛在 PPh3 和 LiOH 存在下在水中的一锅 Wittig 反应。大多数烯烃化反应在含有 1.2 M LiCl 的回流水中在 5–120 分钟内完成，以 71–97% 的收率提供 E:Z 异构体比例为 100:0–55:45 的烯烃产物。
• Cascade Nucleophilic Addition−Cyclic Michael Addition of Arynes and Phenols/Anilines Bearing Ortho α,β-Unsaturated Groups: Facile Synthesis of 9-Functionalized Xanthenes/Acridines
  作者：Xian Huang、Tiexin Zhang

  DOI：10.1021/jo902311a

  日期：2010.1.15

  A facile synthesis of xanthenes and acridines based on a cascade nucleophilic addition−cyclic Michael addition process of arynes and phenols/anilines substituted with α,β-unsaturated groups at the ortho positions is described. The reaction has also been successfully extended to the synthesis of 9-spiro-xanthene and acridine derivatives with potential biochemical interest.

  描述了基于芳烃和邻位被α，β-不饱和基团取代的苯酚/苯胺的级联亲核加成-迈克尔环加成反应的黄嘌呤和a啶的简便合成方法。该反应也已成功地扩展到具有潜在生物化学意义的9-螺并氧杂蒽和a啶衍生物的合成。
• 3-phenoxy-4-pyridazinol derivatives and herbicide composition containing the same
  申请人：Tsukamoto Yoshihisa

  公开号：US20050037925A1

  公开（公告）日：2005-02-17

  A compound represented by the formula: [wherein R 1 represents a hydrogen atom, a halogen, atom, alkyl group, etc., R 2 represents a hydrogen atom, a halogen atom, alkyl group, etc., R 3 , R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substituteable cycloalkyl group, etc., or R 3 , R 4 , R 5 , R 6 and R 7 may form a ring which may be substituted, which is formed by the adjacent two of them with carbon atoms to which the respective substituents are bonded, m and n each independently represent 0 or 1.] a salt thereof, an ester derivative thereof and an agricultural chemical containing the same as an effective ingredient, and a herbicidal composition containing the compound and a second herbicidally active compound as effective ingredients.

  一种化合物由以下式子表示：[其中R1代表氢原子，卤素原子，烷基团等，R2代表氢原子，卤素原子，烷基团等，R3，R4，R5，R6和R7各自独立地代表氢原子，卤素原子，可替换的烷基团，可替换的烯基团，炔基团，可替换的环烷基团等，或R3，R4，R5，R6和R7可以形成一个环，该环可以被取代，该环由相邻的两个碳原子形成，这些碳原子与相应的取代基团相连，m和n各自独立地代表0或1。]其盐，酯衍生物及含有该化合物为有效成分的农药，以及含有该化合物和第二种草甘膦活性化合物为有效成分的除草剂组合物。
• 3-Phenoxy-4-pyridazinol derivatives and herbicidal composition containing the same
  申请人：Tsukamoto Yoshihisa

  公开号：US20100041555A1

  公开（公告）日：2010-02-18

  A compound represented by the formula: [wherein R 1 represents a hydrogen atom, a halogen atom, alkyl group, etc., R 2 represents a hydrogen atom, a halogen atom, alkyl group, etc., R 3 , R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substitutable cycloalkyl group, etc., or R 3 , R 4 , R 5 , R 6 and R 7 may form a ring which may be substituted, which is formed by the adjacent two of them with carbon atoms to which the respective substituents are bonded, m and n each independently represent 0 or 1.] a salt thereof, an ester derivative thereof and an agricultural chemical containing the same as an effective ingredient, and a herbicidal composition containing the compound and a second herbicidally active compound as effective ingredients.

  一种化合物，其化学式为：[其中R1代表氢原子、卤素原子、烷基等，R2代表氢原子、卤素原子、烷基等，R3、R4、R5、R6和R7各自独立地代表氢原子、卤素原子、可替换的烷基、可替换的烯基、炔基、可替换的环烷基等，或R3、R4、R5、R6和R7可形成一个环，该环可以被取代，由它们中的相邻两个碳原子形成，各自带有相应的取代基，m和n各自独立地代表0或1。]其盐、酯衍生物和含有该化合物作为有效成分的农药，以及含有该化合物和第二种除草活性化合物作为有效成分的除草剂组合物。