2-((3,4-dimethoxyphenyl)(hydroxy)methyl)acrylonitrile

• 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: 2-((3,4-dimethoxyphenyl)(hydroxy)methyl)acrylonitrile
• 英文别名: 2-[(3,4-dimethoxyphenyl)hydroxymethyl]acrylonitrile；2-[(3,4-Dimethoxyphenyl)-hydroxymethyl]prop-2-enenitrile
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: SWUGRXNCUVFHAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((3,4-dimethoxyphenyl)(hydroxy)methyl)acrylonitrile 在 硫酸 、 氢溴酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 (2Z)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido]methyl}-3-(3,4-dimethoxyphenyl)prop-2-enenitrile
  参考文献：
  名称：

  喹啉并吡唑结构的多组分级联组件

  摘要：

  通过多米诺反应的应用，开发了一种高效、多组分的方案，用于构建具有高立体选择性的功能化喹啉并吡唑支架。所有喹啉并吡唑均在无溶剂和无催化剂条件下合成，无需后处理或柱层析。

  DOI：

  10.1002/ejoc.201301422
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 丙烯腈 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以71%的产率得到2-((3,4-dimethoxyphenyl)(hydroxy)methyl)acrylonitrile
  参考文献：
  名称：

  烯基腈透射式烯烃化：推定的木质素“ Morinol I”的合成

  摘要：

  格氏试剂触发与α'-羟基丙烯腈的加成消除反应，从而选择性地生成Z-烯腈。由格氏试剂，丙烯腈和醛组成的Z链烯腈的模块化组装是理想的立体选择性合成烯烃的方法，如推定的木脂素“ morinol I”所示。

  DOI：

  10.1002/ejoc.201101235

文献信息

• A highly regio- and stereoselective Pd-catalyzed tandem allylic rearrangement/intramolecular decarboxylative coupling of aryl propiolates derived from Baylis–Hillman adducts
  作者：Tummanapalli Satyanarayana、Dhanunjaya Naidu Vangapandu、Parthasarathy Muthuraman、Shashidhar Nizalapur

  DOI：10.1016/j.tetlet.2015.02.125

  日期：2015.4

  A highly regio- and stereoselective Pd-catalyzed tandem allylic rearrangement/intramolecular decarboxylative coupling of aryl propiolates derived from Baylis–Hillman alcohols leading to the formation of an important class of 1,5-diarylpent-1-en-4-ynes has been developed. The aryl propiolates of Baylis–Hillman alcohols derived from methyl acrylate provided exclusively (E)-1,5-diarylpent-1-en-4-ynes

  已经开发出高度区域选择性和立体选择性的Pd催化串联烯丙基重排/分子内脱羧的衍生自Baylis-Hillman醇的丙酸芳酯，导致形成一类重要的1,5-二芳基戊-1-烯-4-炔。丙烯酸甲酯衍生的Baylis–Hillman醇的芳基丙酸酯仅提供（E）-1,5-二芳基-1-en-4-ynes，而丙烯腈衍生的Baylis–Hillman醇的芳基丙酸酯仅提供（Z）-1 ，5-二芳基戊-1-烯-4-炔。
• Allylic and Allenic Halide Synthesis via NbCl₅- and NbBr₅-Mediated Alkoxide Rearrangements
  作者：P. C. Ravikumar、Lihua Yao、Fraser F. Fleming

  DOI：10.1021/jo901287f

  日期：2009.10.2

  Addition of NbCl5 or NbBr5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metalla-halo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared

  将NbCl 5或 NbBr 5 添加到一系列镁、锂或钾的烯丙基或炔丙基醇盐中直接提供烯丙基或烯丙基卤化物。卤化通过金属-卤-[3,3] 重排正式发生，尽管协同、离子和直接置换机制似乎具有竞争性。烯烃的转位对于通过亲核加成、去质子化或还原制备的烯丙基醇盐同样有效。实验上，五卤化铌卤化反应迅速，萃取后可提供基本纯的 ( E )-烯丙基或烯丙基卤化物，适用于一系列脂肪族和芳香族醇、醛和酮。
• Montmorillonite K10 Clay-catalyzed Synthesis of Substituted 1-Aryl Indenes from Baylis–Hillman Adducts
  作者：Ponnusamy Shanmugam、Paramasivan Rajasingh

  DOI：10.1246/cl.2005.1494

  日期：2005.11

  An eco-friend method for the synthesis of 1-aryl indenes from Baylis–Hillman adducts using Mont. K10 and microwave combination as catalyst system and a procedure for the synthesis of β-phenyl-subst...

  使用 Mont. 从 Baylis-Hillman 加合物合成 1-芳基茚的环保方法。K10和微波组合作为催化剂体系和合成β-苯基-底物的方法...
• A facile route for the synthesis 1,4-disubstituted tetrazolone derivatives and evaluation of their antimicrobial activity
  作者：Amlipur Santhoshi、Partha Sarathi Sadhu、Rekulapally Sriram、Chebolu Naga Sesha Sai Pavan Kumar、Budde Mahendar、Manda Sarangapani、Vaidya Jayathirtha Rao

  DOI：10.1007/s00044-012-0331-4

  日期：2013.7

  A facile route for the synthesis of 20 new 1,4-disubstituted tetrazolone derivatives from allyl bromides of Baylis-Hillman adducts and various 1-substituted tetrazolones is described. All the synthesized compounds were screened for in vitro antibacterial and antifungal activity. Out of 20 newly synthesized compounds 16 compounds showed very good activity against the Gram-positive bacteria Bacillus subtilis compare to the standard drug ciprofloxacin. The compounds 7b, 7n and 7o showed remarkable activity against both the Gram-positive bacteria B. subtilis and Staphylococcus aureus. Two compounds 7l and 7o showed very good activity against the Gram-negative bacteria Escherichia coli. The compounds, when tested for antifungal activity four compounds- 7b, 7l, 7o and 7s- showed very good activity against the strain Aspergillus niger, whereas seven compounds- 7e, 7g, 7h, 7l, 7o and 7s- display good activity against Candida albicans. Compounds 7b, 7e, 7g, 7l and 7o exhibited very good-to-high activity towards all the strains tested.
• Antimalarial activity of 3-hydroxyalkyl-2-methylene-propionic acid derivatives
  作者：Mrinal K. Kundu、N. Sundar、Srinivas K. Kumar、Sujata V. Bhat、Sukla Biswas、Neena Valecha

  DOI：10.1016/s0960-894x(99)00057-8

  日期：1999.3

  Several Baylis-Hillman adducts and their derivatives were synthesized and evaluated as targeted potential anti-malarials, The compounds 4, 7 and 9 were found to have highest potency against P. falciparum in vitro. The in vivo test result of compound 4 and 9 against P. berghei demonstrated activity at 80 mg/Kg dose level. (C) 1999 Elsevier Science Ltd. All rights reserved.