2-((4-bromophenyl)(hydroxy)methyl)acrylonitrile | 282089-45-6

• 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-((4-bromophenyl)(hydroxy)methyl)acrylonitrile
• 英文别名: 3-Hydroxy-2-methylene-3-(4-bromophenyl)propanenitrile；2-[(4-bromophenyl)-hydroxymethyl]prop-2-enenitrile
• CAS: 282089-45-6
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: IURFBZHUSDCBBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  2-((4-bromophenyl)(hydroxy)methyl)acrylonitrile 在 sodium nitrate 、 1-己基-3-甲基咪唑硫酸氢盐 、 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 2-((Z)-5-((Z)-3-(4-bromophenyl)-2-cyanoallylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of new epalrestat analogues as aldose reductase inhibitors (ARIs)

  摘要：

  Baylis-Hillman chemistry derived four series of new epalrestat analogues were synthesized. Three structural changes are introduced in these 39 new epalrestat analogues synthesized. All compounds were evaluated for their in vitro aldose reductase inhibitory (ALR) activity. Biological activity data indicates that compounds 6, 16, 19, 28 and 29 are potent and the activity is in the range of reference drug, epalrestat. Molecular modelling studies were performed to understand the binding interactions of these active molecules with the ALR protein. Molecular docking data indicates the key interactions of epalrestat were retained in some of the active compounds whereas some new interactions were noticed for other molecules. The modifications introduced on epalrestat have impact for developing a new-type of ALR inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.043
• 作为产物：
  描述：

  2-[(4-bromo-phenyl)-hydroxy-methyl]-acrylic acid methyl ester 在 三乙烯二胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2-((4-bromophenyl)(hydroxy)methyl)acrylonitrile
  参考文献：
  名称：

  Claudio Jr.; Silva, Fabio P.L.; De Oliveira, Ramon G., Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2220 - 2224

  摘要：

  DOI：

文献信息

• N-Acylazole mediated stereoselective and regioselective synthesis ofN-substituted azole acrylonitriles
  作者：Osman AYDIN、Şule KÖKTEN、Hakan ÜNVER、İlhami ÇELİK

  DOI：10.3906/kim-1903-56

  日期：——

  Regioand stereoselective synthesis of N -substituted azole acrylonitriles has been achieved smoothly in N,N -dimethylformamide (DMF) in the presence of potassium carbonate (K2 CO3) as a base catalyst. N -Substituted azole acrylonitriles were obtained in moderate to good yields (39%–87%) with a one-pot reaction between readily available N -acetylazoles and Baylis-Hillman nitriles. The structural determinations

  在碳酸钾（K2CO3）作为碱催化剂存在下，在N，N-二甲基甲酰胺（DMF）中顺利实现了N-取代的唑丙烯腈的区域和立体选择性合成。在容易获得的N-乙酰基唑与Baylis-Hillman腈之间进行一锅法反应后，以中等至良好的收率（39％–87％）获得了N-取代的唑丙烯腈。结构测定通过NOESY 1 H NMR和X射线晶体学完成。
• An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis–Hillman reaction
  作者：Thatikonda Narendar Reddy、Bikshapathi Raktani、Ramesh Perla、Mettu Ravinder、Jayathirtha Rao Vaidya、N. Jagadeesh Babu

  DOI：10.1039/c7nj01965c

  日期：——

  Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis–Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity

  在本文中，已经开发了一种在无催化剂条件下使用羟胺/甲醇系统从Baylis-Hillman加合物的醛制备烯丙基酰胺的简便有效的方法。研究了溶剂和温度对反应的影响以及苯环上的取代基。该方法的优点如操作简单，中等至极好的收率，较短的反应时间和简单的反应过程等得到了最好的证明。最重要的是，在没有催化剂和外部氧化剂的情况下，反应平稳进行。
• Design, synthesis, and biological evaluation of 4-H pyran derivatives as antimicrobial and anticancer agents
  作者：Thatikonda Narendar Reddy、Mettu Ravinder、Raktani Bikshapathi、Pombala Sujitha、C. Ganesh Kumar、Vaidya Jayathirtha Rao

  DOI：10.1007/s00044-017-1982-y

  日期：2017.11

  A series of pyran derivatives (5–27) were synthesized in good yields by utilizing Baylis–Hillman chemistry and were further investigated for their in vitro anticancer, antibacterial, and antifungal activities. Most of the tested compounds exhibited promising antibacterial activity as compared to the standard towards Gram-positive bacterial strains. The compounds 5–7, 11–13, and 17–19 displayed two-fold

  利用Baylis–Hillman化学方法以高收率合成了一系列吡喃衍生物（5–27），并对其体外抗癌，抗菌和抗真菌活性进行了进一步研究。与针对革兰氏阳性细菌菌株的标准品相比，大多数测试化合物均显示出有希望的抗菌活性。化合物5-7，11-13和17-19显示的两个倍高的活性，而化合物21显示出针对4倍高的抗菌活性的金黄色葡萄球菌相比，新霉素标准96 MTCC。这些化合物中的一些对所有测试的真菌菌株均表现出中等的抗真菌活性。两种化合物图16和23显示了对选定的四种人类癌细胞系如A549，DU145，HeLa和MCF7的有希望的抗癌活性。
• The First One-Pot Synthesis of Morita-Baylis-Hillman Adducts Starting Directly from Alcohols
  作者：Lal Yadav、Vishnu Srivastava、Rajesh Patel

  DOI：10.1055/s-0029-1219577

  日期：2010.4

  The first example of one-pot oxidative carbon-carbon bond formation via the Morita-Baylis-Hillman reaction using alcohols is reported. The protocol involves silica gel-DABCO catalyzed oxidation of alcohols to aldehydes with chloramine-T followed by their Morita-Baylis-Hillman reaction with acrylonitrile or methyl acrylate to give 70-87% overall yields of the corresponding Morita-Baylis-Hillman adducts

  报道了使用醇通过 Morita-Baylis-Hillman 反应形成一锅氧化碳-碳键的第一个例子。该协议涉及硅胶-DABCO 用氯胺-T 催化将醇氧化为醛，然后与丙烯腈或丙烯酸甲酯进行 Morita-Baylis-Hillman 反应，得到 70-87% 的相应 Morita-Baylis-Hillman 加合物的总产率。目前的工作开辟了一条新的、有效的合成路线，以单锅操作直接从醇中合成 Morita-Baylis-Hillman 加合物。
• Triphosgene mediated chlorination of Baylis–Hillman adducts
  作者：NARENDER REDDY THATIKONDA、NAGA SESHA SAI PAVAN KUMAR CHEBOLU、MAHENDAR BUDDE、JAYATHIRTHA RAO VAIDYA

  DOI：10.1007/s12039-012-0243-3

  日期：2012.3

  method for the preparation of allyl chlorides from Baylis–Hillman adducts has been developed using triphosgene/pyridine system. This method is best illustrated by its advantages like operational simplicity, excellent yields, short reaction time, simple procedure and stereoselectivity. The preparation of allyl chlorides from Baylis-Hillman adducts has been described using triphosgene & pyridine system

  使用三光气/吡啶体系开发了一种从Baylis-Hillman加合物制备烯丙基氯的有效方法。该方法的优点是操作简便，产率高，反应时间短，操作步骤简单和立体选择性好，这是最好的例证。 已经描述了使用三光气和吡啶体系从Baylis-Hillman加合物制备烯丙基氯。该方法的效率可以通过一些优点来最好地说明，例如操作简便，产率高，反应时间短，操作简单和立体选择性。