(E)-2-(bromomethyl)-3-(4-chlorophenyl)acrylonitrile | 139413-83-5

• 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)-2-(bromomethyl)-3-(4-chlorophenyl)acrylonitrile
• 英文别名: (E)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enenitrile
• CAS: 139413-83-5
• 化学式: C₁₀H₇BrClN
• 分子量: 256.529
• InChiKey: CIBZJWWVXRGMBH-UITAMQMPSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  342.4±37.0 °C(Predicted)
• 密度：
  1.552±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-(bromomethyl)-3-(4-chlorophenyl)acrylonitrile 在 盐酸羟胺 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 (E)-3-(4-chlorophenyl)-2-({2-[(E)-(hydroxyimino)methyl]phenoxy}methyl)acrylonitrile
  参考文献：
  名称：

  使用Baylis-Hillman衍生物的分子内1,3-偶极氮氧化物环加成反应：立体选择性合成三环铬异恶唑啉

  摘要：

  首次描述了通过使用Baylis-Hillman衍生物的分子内1,3-偶极腈氧化环加成（INOC）反应构建三环苯并异恶唑啉骨架的新方案。INOC反应导致一类新的有角度取代的稠合三环铬异异唑啉，以独特的方式产生了两个环和两个相邻的立体中心，其中一个是全碳四元中心。以高度立体选择性的方式以良好的收率获得三环色异恶唑啉。 1,3-偶极一氧化氮环加成-铬异恶唑啉-立体选择性合成-三环骨架

  DOI：

  10.1055/s-0031-1289707
• 作为产物：
  描述：

  2-[(4-chlorophenyl)hydroxymethyl]acrylonitrile 在 硫酸 、 氢溴酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (E)-2-(bromomethyl)-3-(4-chlorophenyl)acrylonitrile
  参考文献：
  名称：

  从 Baylis-Hillman 溴化物高效合成 N-烯丙基化 2-硝基亚氨基咪唑烷类似物

  摘要：

  摘要 使用碳酸钾作为碱，可以有效地制备各种 Baylis-Hillman 衍生的新型 N-烯丙基化 2-硝基亚氨基咪唑烷类似物。简单的后处理程序、优异的收率和温和的反应条件是该方法的显着特点。筛选所有合成的化合物对四龄蚊子幼虫库蚊的杀幼虫活性。图形概要

  DOI：

  10.1080/00397911.2016.1255333

文献信息

• Mild and practical stereoselective synthesis of (Z)- and (E)-allyl bromides from Baylis–Hillman adducts using Appel agents (PPh3/CBr4): a facile synthesis of semiplenamides C and E
  作者：Biswanath Das、Kongara Damodar、Nisith Bhunia、Boddu Shashikanth

  DOI：10.1016/j.tetlet.2009.02.132

  日期：2009.5

  Appel agents (PPh3/CBr4) have been utilized for high-yielding stereoselective synthesis of (Z)- and (E)-allyl bromides from Baylis–Hillman adducts at room temperature. The method has been applied for the synthesis of naturally occurring bioactive fatty acid amides, semiplenamides C and E.

  在室温下，Appel试剂（PPh 3 / CBr 4）已用于从Baylis-Hillman加合物中高产率地立体选择性合成（Z）-和（E）-烯丙基溴。该方法已用于合成天然存在的生物活性脂肪酸酰胺，半乳糖C和E。
• A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction
  作者：Manickam Bakthadoss、Varathan Vinayagam

  DOI：10.1039/c5ob01060h

  日期：——

  An efficient method towards the synthesis of quinoline fused tricyclic compounds involving an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction utilizing Baylis–Hillman derivatives in good yields has been described for the first time. A highly functionalized tricyclic framework was created by forming two rings and two adjacent stereocentres through the formation of two N–C bonds, one

  首次描述了一种有效的方法，该方法利用Baylis-Hillman衍生物以高收率合成涉及分子内1,3-偶极腈氧化环加成反应的喹啉稠合三环化合物。通过以高度区域和非对映选择性的方式形成两个N–C键，一个C–C键和一个O–C键，形成两个环和两个相邻的立体中心，从而创建了高度功能化的三环骨架。
• A FACILE SYNTHESIS OF [E]-α-CYANOCINNAMIC ALDEHYDES FROM BAYLIS-HILLMAN ADDUCTS
  作者：Subramanian Ravichandran

  DOI：10.1081/scc-100104470

  日期：2001.1.1

  A facile synthesis of stereochemically pure [E]-α-cyanocinnamic aldehydes from Baylis-Hillman adducts is described.

  描述了从 Baylis-Hillman 加合物中轻松合成立体化学纯 [E]-α-氰基肉桂醛。
• Metal-free, regio- and stereoselective S-methylation/phenylation of allyl halides using sulfoxides as sulfenylating agent
  作者：Rakhee Choudhary、Rekha Bai、Pratibha Singh、Mahesh C. Sharma、Satpal Singh Badsara

  DOI：10.1016/j.tet.2017.05.088

  日期：2017.7

  A DCP promoted metal-free, regio and stereoselective S-methylation/phenylation of allyl halides using sulfoxides as sulfenylating agent is described. A variety of multifunctional allyl halides underwent S-methylation and S-phenylation by using dimethyl sulfoxide (DMSO) and diphenyl sulfoxide (DPSO) under the reaction conditions employed to provide the resulting thioethers in good to excellent yields

  描述了使用亚砜作为亚磺酰化剂的DCP促进的烯丙基卤化物的无金属的，区域性和立体选择性的S-甲基化/苯基化。通过使用二甲基亚砜（DMSO）和二苯基亚砜（DPSO），在用于以良好或优异的收率良好地提供所得硫醚的反应条件下，对各种多功能的卤代烯进行S-甲基化和S-苯基化。
• 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.