(E)-2-(benzo[d]thiazol-2-yl)-3-(4-methoxyphenyl)acrylonitrile | 85460-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (E)-2-(benzo[d]thiazol-2-yl)-3-(4-methoxyphenyl)acrylonitrile
• 英文别名: (E)-2-(1,3-benzothiazol-2-yl)-3-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 85460-28-2
• 化学式: C₁₇H₁₂N₂OS
• 分子量: 292.361
• InChiKey: APOSHAYDQCAPKA-JLHYYAGUSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  487.6±55.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(benzo[d]thiazol-2-yl)-3-(4-methoxyphenyl)acrylonitrile 、 茴香烯 反应 36.0h， 以42%的产率得到(1R*,2R*,3S*)-1,3-bis(4-methoxyphenyl)-2-methyl-2,3-dihydro-1H-pyrido<2,1-b>benzothiazole-4-carbonitrile
  参考文献：
  名称：

  Benzylidenecyanomethyl-1,3-benzazoles as 1-Aza-1,3-butadienes.

  摘要：

  报道了苄叉氰甲基-1,3-苯并噻唑和-1,3-苯并噆唑2a-f作为1-氮-1,3-丁二烯的Diels-Alder反应。这些二烯2通过构成杂芳香环而稳定了的亚胺基团，与缺电子和富电子的二烯亲和体3a-c反应，选择性地生成相应的环加成产物4-6。内消旋体系的环加成反应8a-d通过外向过渡态顺利进行，立体选择性地得到多环化合物9a-d，收率良好至优秀。

  DOI：

  10.1248/cpb.42.1367
• 作为产物：
  描述：

  3-benzothiazol-2-yl-2-hydroxyimino-propionic acid 在 哌啶 、 乙醇 、 乙酸酐 作用下， 生成 (E)-2-(benzo[d]thiazol-2-yl)-3-(4-methoxyphenyl)acrylonitrile
  参考文献：
  名称：

  Borsche; Doeller, Justus Liebigs Annalen der Chemie, 1939, vol. 537, p. 53,65

  摘要：

  DOI：

文献信息

• Magnetic nanoparticle supported amine: An efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation
  作者：Anguo Ying、Limin Wang、Fangli Qiu、Huanan Hu、Jianguo Yang

  DOI：10.1016/j.crci.2014.05.012

  日期：2015.2

  Résumé Amine functionalized silica coated Fe3O4 nanoparticles (SiO2@MNP-A) were successfully prepared as a novel heterogeneous amine. The catalyst was characterized by XRD, FT-IR, TEM, magnetic measurement, elemental analysis and was found to be a magnetically separable and highly active catalyst for ambient Knoevenagel condensation of aromatic aldehydes and α-aromatic (heteroaromatic or polyaromatic)-substituted methylene compounds in water under ultrasonic irradiation to afford the corresponding products in good to excellent yields. Very interestingly, SiO2@MNP-A successfully catalyze the reaction of the non-cyano substituted compound with benzaldehyde to achieve a key intermediate for the preparation of Atorvastatin calcium in green and atom-economic manner. In addition, the catalyst SiO2@MNP-A can be reused for 8 times without any obvious loss of its activity. The role of ultrasonication in the Knoevenagel condensation was also discussed with the assistance of UV–vis spectrometry.

  摘要 成功制备了氨基功能化的二氧化硅包覆的Fe3O4纳米颗粒（SiO2@MNP-A），作为一种新型的异相胺催化剂。通过XRD、FT-IR、TEM、磁性测量和元素分析对催化剂进行了表征，结果表明其为一种可磁性分离的高活性催化剂，用于在超声辐射下在水中进行芳香醛和α-芳香（含异构体或多芳香）取代亚甲基化合物的室温Knoevenagel缩合反应，能在良好到优异的产率下获得相应产物。非常有趣的是，SiO2@MNP-A成功催化了非氰取代化合物与苯甲醛的反应，从而实现了以绿色和原子经济的方式制备阿托伐他汀钙的关键中间体。此外，催化剂SiO2@MNP-A可重复使用8次，而其活性几乎没有明显损失。还通过紫外-可见光谱法讨论了超声对Knoevenagel缩合反应的影响。
• Knoevenagel Condensation Reaction Using Ionic Liquid [ADPQ][CF3SO3] as Green and Reusable Catalyst
  作者：Xiaochong Gao、Can Gao、Ruichang Gao

  DOI：10.14233/ajchem.2015.17821

  日期：——

  Knoevenagel condensation reaction of aromatic aldehydes with some active methylene compounds proceeded efficiently without solvent using ionic liquids as catalyst. The experimental results show that these ionic liquids have good catalytic activities to the Knoevenagel condensation with a wide range of reactant. The reactions are carried out in a few minutes with high yields. The ionic liquids can be recycled and reused for 4 times without noticeably decreasing the catalytic activity.

  芳香醛与一些活性亚甲基化合物的Knoevenagel缩合反应在无溶剂条件下利用离子液体作为催化剂高效进行。实验结果表明，这些离子液体对Knoevenagel缩合反应具有良好的催化活性，适用范围广。反应在几分钟内完成，产率较高。离子液体可以回收再利用4次，催化活性没有明显降低。
• Facile synthesis of new functionalized 3,4-dihydro-2H-pyrroles using 2-isocyanoacetates
  作者：Huijie Zhang、Kaikai Lv、Lanping Ma、Yongliang Zhang、Ting Yu、Lin Chen、Xin Wang、Jingkang Shen、Tao Meng

  DOI：10.1016/j.tetlet.2020.151944

  日期：2020.6

  A one-step synthesis of novel functionalized 3,4-dihydro-2H-pyrroles from 2-isocyanoacetates and readily synthesized acrylonitriles is reported. The reaction proceeds smoothly under mild conditions with high efficiency. The structures of two representative structures, 3a and 3m, were confirmed by X-ray crystallographic analysis.

  据报道，由2-异氰基乙酸酯和容易合成的丙烯腈一步合成新型的官能化的3，4-二氢-2 H-吡咯。反应在温和的条件下高效高效地进行。通过X射线晶体学分析确认了两个代表性结构3a和3m的结构。
• Heterocyclic Fused Rings with Bridgehead Nitrogen Atoms: Single-Step Synthesis of Azolo[1″,2″:1′,2′]pyrido[5′,6′:5,4]pyrimido[1,6-a]benzimidazole; Pyrido[1,2-a]benzimidazole; Pyrido[4″,5″:2′,3′]pyrido[6′,5′:4,5]pyrimido-[1,6-a]benzimidazole and Polysubsti
  作者：M. A. Raslan

  DOI：10.1002/jccs.200000133

  日期：2000.8

  A one-step synthesis of the title compounds by the reaction of arylidene-lH-benzimidazol-2-ylacetonitriles 1a-d with 2-cyanomethylbenzimidazole derivatives 2a,b is reported.

  报道了通过亚芳基-1H-苯并咪唑-2-基乙腈1a-d与2-氰基甲基苯并咪唑衍生物2a、b的反应一步合成标题化合物。
• Regioselective synthesis of polysubstituted 3,3′-bi-1H-pyrazole derivatives via 1,3-dipolar cycloaddition reactions
  作者：Ahmad M. Farag、Nabila A. Kheder、Milos Budesinsky

  DOI：10.1016/s0040-4020(97)00583-8

  日期：1997.7

  add regioselectively to α-(benzothiazol-2-yl)cinnamonitriles 3 and α-(1-methylbenzimidazol-2-yl)cinnamonitriles 7 to yield exclusively the cycloadducts 5,5′-dicyano-4,4′,5,5′-tetrahydro[3,3′-bi-1H-pyrazoles] 4 and 8, respectively. Compounds 4 and 8 undergo aromatization via thermal elimination of hydrogen cyanide under basic conditions to afford the corresponding 3,3′-bi-1H-pyrazole derivatives 6 and

  N，N'-二芳基双腈酰亚胺2选择性地向α-（苯并噻唑-2-基）肉桂腈3和α-（1-甲基苯并咪唑-2-基）肉桂腈7添加区域选择性地生成环加合物5,5'-dicyano-4， 4′，5，5′-四氢[3，3′-bi-1H-吡唑] 4和8。化合物4和8通过在碱性条件下热消除氰化氢进行芳构化，分别得到相应的3,3'-bi-1H-吡唑衍生物6和10。讨论了环加合物的区域化学。