| 1394867-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1394867-19-6
• 化学式: C₁₄H₁₄N₂O₈
• 分子量: 338.274
• InChiKey: HIUBEPOWCHRBKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  138.88
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-氨基苯并咪唑 、 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以51%的产率得到
  参考文献：
  名称：

  来自森田–贝利斯–希尔曼乙酸盐的功能化二氢偶氮嘧啶衍生物：乙酰胆碱酯酶作为抑制剂的合成和研究†

  摘要：

  通过硝基苯乙烯衍生的MBH乙酸酯和氨基唑衍生物与γ-α的一锅反应，在室温下以中等至良好的产率合成了各种各样的二氢[1,5]偶氮[1,2 - a ]嘧啶2-酯环化。该反应涉及级联的S N 2反应，随后是分子内迈克尔加成环化反应，并生成两个新的碳氮键。通过单X射线晶体分析进一步证实了该结构。二氢苯并咪唑并嘧啶衍生物对乙酰胆碱酯酶（AChE）的对接和体外研究已经完成，化合物3d和3e表现出有效的抑制活性，并具有IC 50 分别为46.8 nM和42.5 nM。

  DOI：

  10.1039/c6ra12507g

文献信息

• Regiospecific synthesis of arenofurans via cascade reactions of arenols with Morita–Baylis–Hillman acetates of nitroalkenes and total synthesis of isoparvifuran
  作者：Tarun Kumar、Shaikh M. Mobin、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2013.04.023

  日期：2013.6

  A cascade process involving an SN2′ reaction and an intramolecular oxa-Michael addition has been developed by treating Morita–Baylis–Hillman acetates of nitroalkenes with arenols, such as β-naphthols, α-naphthols, and substituted phenols under basic conditions. The products, arenofurans, are formed as single regioisomers in good to excellent yield in most cases. The methodology has been successfully

  通过在碱性条件下用戊烯（如β-萘酚，α-萘酚和取代酚）处理硝基烯烃的Morita-Baylis-Hillman乙酸酯，已开发出一种涉及S N 2'反应和分子内氧杂-Michael加成的级联过程。在大多数情况下，苯并呋喃类产品以单一的区域异构体形式形成，收率好至极佳。该方法已成功地用于抗真菌剂异戊呋喃的全合成。
• Synthesis of Imidazopyridines from the Morita–Baylis–Hillman Acetates of Nitroalkenes and Convenient Access to Alpidem and Zolpidem
  作者：Divya K. Nair、Shaikh M. Mobin、Irishi N. N. Namboothiri

  DOI：10.1021/ol3020418

  日期：2012.9.7

  have been synthesized through a one-pot, room temperature, and reagent-free reaction between MBH acetates of nitroalkenes and 2-aminopyridines. The reaction involves a cascade inter-intramolecular double aza-Michael addition of 2-aminopyridines to MBH acetates. Our methodology is marked by excellent yield, regioselectivity and, above all, adaptability to synthesize imidazopyridine-based drug molecules

  通过一锅，室温，硝基烯烃的MBH乙酸酯与2-氨基吡啶之间的无试剂反应，已经合成了多种官能化的咪唑并[1,2-a]吡啶。该反应涉及2-氨基吡啶向MBH乙酸酯的级联的分子间双氮杂-Michael加成。我们的方法具有出色的收率，区域选择性以及最重要的是对合成咪唑并吡啶基药物分子（如Alpidem和Zolpidem）的适应性。
• One-pot regioselective synthesis of functionalized and fused furans from Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes
  作者：Vaijinath Mane、Tarun Kumar、Sourav Pradhan、Savita Katiyar、Irishi N. N. Namboothiri

  DOI：10.1039/c5ra11471c

  日期：——

  Highly functionalized and fused furans have been synthesized via cascade reactions of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes with active methylene compounds. The reactions involving SN2′-intramolecular Michael addition or Michael addition-intra-molecular nucleophilic substitution take place in a regioselective manner to afford synthetically and biologically useful furans in

  通过Morita–Baylis–Hillman和Rauhut–Currier硝基烯烃与活性亚甲基化合物的加成反应，可以合成高度官能化和熔融的呋喃。涉及S N 2'-分子内迈克尔加成或迈克尔加成-分子内亲核取代的反应以区域选择性方式发生，以中等至良好的产率提供合成和生物学上有用的呋喃。
• Metal-Free and Regioselective Synthesis of Functionalized α-Carbolines via [3 + 3] Annulation of Morita–Baylis–Hillman Acetates of Nitroalkenes with Iminoindolines
  作者：Sudheesh T. Sivanandan、Irishi N. N. Namboothiri

  DOI：10.1021/acs.joc.1c00422

  日期：2021.6.18

  α-carbolines from secondary Morita–Baylis–Hillman (MBH) acetates of nitroalkenes is presented. The cascade reaction of MBH acetates with tosyliminoindolines occurs regioselectively to form various α-carbolines with a wide substrate scope. The reaction involves mild conditions, and the products are formed in high yields within a short reaction time. The amenability of the reaction to scale up and synthetic

  提出了一种从硝基烯烃的二级 Morita-Baylis-Hillman (MBH) 乙酸酯合成取代 α-咔啉的简便、无金属方法。MBH 乙酸酯与甲苯磺酰基二氢吲哚的级联反应发生区域选择性，以形成具有广泛底物范围的各种 α-咔啉。该反应条件温和，反应时间短，产物收率高。已经证明了该反应对产品的放大和合成应用的适应性。
• (3 + 3) Annulation of Nitroallylic Acetates with Stabilized Sulfur Ylides for the Synthesis of 2-Aryl Terephthalates
  作者：Lakshminarayana Satham、Irishi N. N. Namboothiri

  DOI：10.1021/acs.joc.8b00917

  日期：2018.8.17

  A novel (3 + 3) annulation approach has been developed for the synthesis of 2-aryl terephthalates from nitroallylic acetates and stabilized sulfur ylides. The 2-aryl terephthalates, which are also biaryls bearing a terephthalate moiety, are formed through a cascade of reactions such as a γ-selective SN2′ reaction, γ-selective intramolecular Michael addition, and two eliminations in the presence of

  已经开发了一种新颖的（3 + 3）环空方法，用于从硝基烯丙基乙酸酯和稳定的硫酰化物合成对苯二甲酸2-芳基酯。的2-芳基对苯二甲酸酯，其也是联芳基带有对苯二甲酸乙二醇酯部分，通过反应器的级联形成诸如γ-选择性小号Ñ 2'反应，γ-选择性分子内迈克尔加成和两个抵销在Cs的存在2室温下CH 3 CN中的CO 3。该产品是法尼基转移酶抑制剂的正式前体，也是聚合物化学中的潜在单体。