2-[(2-chloroquinolin-3-yl)hydroxymethyl]acrylonitrile | 1248570-24-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(2-chloroquinolin-3-yl)hydroxymethyl]acrylonitrile
• 英文别名: (+/-)-2-[(2-chloroquinolin-3-yl)(hydroxy)methyl]prop-2-enenitrile；2-[(2-Chloroquinolin-3-yl)-hydroxymethyl]prop-2-enenitrile
• CAS: 1248570-24-2
• 化学式: C₁₃H₉ClN₂O
• 分子量: 244.68
• InChiKey: CXSQRPZDNCNBOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2-chloroquinolin-3-yl)hydroxymethyl]acrylonitrile 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 1-methyl-1,2-dihydro-benzo[b][1,8]naphthyridine-3-carbonitrile
  参考文献：
  名称：

  2-氯喹啉基-3-甲醛的BH乙酸的无碱胺化：合成N-取代-1,2-二氢苯并[ b ] [1,8]萘啶的简便方法

  摘要：

  从2-氯-3-甲酰基喹啉的BH乙酸酯和活化的烯烃，然后用不同的胺进行乙酰化，可以有效地无锅一锅法合成1,2-二氢苯并[ b ] [1,8]萘啶。这些反应可在很短的时间内完成，并以良好的收率提供了良好的产品。我们进一步探索了具有碳亲核试剂的BH乙酸酯的范围，为在温和条件下以优异的收率合成a啶衍生物提供了一条新途径。

  DOI：

  10.1016/j.tet.2011.01.076
• 作为产物：
  描述：

  苯胺 在 三乙烯二胺 、 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 3.58h， 生成 2-[(2-chloroquinolin-3-yl)hydroxymethyl]acrylonitrile
  参考文献：
  名称：

  Synthesis and antimalarial activity of Baylis-Hillman adducts from substituted 2-chloroquinoline-3-carboxaldehydes

  摘要：

  Various quinoline carboxaldehydes were prepared from corresponding anilides using classical Vilsmeier-Haack reaction conditions and transformed into their Baylis-Hillman adducts. The synthesized Baylis-Hillman adducts were screened for their in vitro antimalarial activity against Plasmodium falciparum. Most of the compounds out of 21 compounds synthesized and screened exhibited substantial antimalarial activity.

  DOI：

  10.1515/hc.2011.024

文献信息

• A Novel Procedure for the Synthesis of Benzo[b][1,8]naphthyridine-3-carboxylate Derivatives from Morita-Baylis-Hillman Adduct Acetates
  作者：Weike Su、Weihui Zhong、Fuliang Lin、Ren’er Chen

  DOI：10.1055/s-0029-1216853

  日期：2009.7

  8]naphthyridine-3-carboxylate derivatives from the reaction of Morita-Baylis-Hillman adduct acetates with primary amines, ammonium acetate or benzenesulfonamides. The approach, which involves readily available starting materials and mild reaction conditions, gives excellent yields after a convenient workup procedure. benzo[b][1,8]naphthyridine-3-carboxylate - Morita-Baylis-Hillman adduct acetates - primary amines

  从Morita-Baylis-Hillman加成乙酸酯与伯胺，乙酸铵或苯磺酰胺的反应中，设计了一种新颖的方法来制备苯并[ b ] [1,8]萘啶-3-羧酸酯衍生物。该方法涉及容易获得的起始原料和温和的反应条件，在方便的后处理步骤后可获得优异的产率。 苯并[ b ] [1,8]萘啶-3-羧酸盐-Morita-Baylis-Hillman加合物乙酸盐-伯胺-乙酸铵-苯磺酰胺
• Synthesis of New Cyano-Quinoline Derivatives by the Baylis–Hillman Reaction
  作者：Fatiha Guenfoud、Amani Direm、Mohammed Laabassi、Nourredine Benali-Cherif

  DOI：10.1007/s10870-012-0325-6

  日期：2012.10

  Quinoline derivatives represent the major class of heterocycles, and a number of preparations have been known since the late 1800s. The quinoline ring system occurs in various natural products, especially in alkaloids. The quinoline skeleton is often used for the design of many synthetic compounds with diverse pharmacological properties. A new quinoline derivative was crystallized from the reaction

  喹啉衍生物代表了杂环的主要类别，自 1800 年代后期以来，已知有多种制备方法。喹啉环系统存在于各种天然产物中，尤其是生物碱中。喹啉骨架通常用于设计许多具有不同药理特性的合成化合物。一种新的喹啉衍生物是从丙烯腈和 2-氯-3-甲酰基喹啉衍生物之间的反应中结晶出来的，而 2-氯-3-甲酰基喹啉衍生物本身是由 Meth Cohn 方法制备的。该反应由 DABCO 催化，产生五种新的 2-[2-氯-喹啉-3-基)-羟基-甲基]-丙烯腈衍生物。7-甲氧基取代的晶体结构在单斜空间群 C2/c 中结晶，a = 17.1090 (7) Å, b = 8.3119 (5) Å, c = 19.7949 (6) Å, β = 101.922 (2) °，
• Facile Metal-Free Synthesis of Phenanthridines by S_N 2′ Reaction/C-H Functionalization/Aromatization through the Reaction of Morita-Baylis-Hillman Acetates with Nitroalkanes
  作者：Tanu Gupta、Jay Bahadur Singh、Kalpana Mishra、Biswajit Maiti、Radhey M. Singh

  DOI：10.1002/ejoc.201701574

  日期：2018.3.7

  The regioselective synthesis of functionalized phenanthridines by the reaction of MBH acetates of 2‐chloroquinoline‐3‐carbaldehydes with nitroalkanes is described. The reaction takes place at room temperature under aerobic conditions.

  描述了2-氯喹啉-3-甲醛的MBH乙酸盐与硝基烷烃的区域选择性合成功能化的菲啶。该反应在有氧条件下在室温下进行。
• Simple and highly diastereoselective access to 3,4-substituted tetrahydro-1,8-naphthyridines from Morita–Baylis–Hillman adducts
  作者：Manoel T. Rodrigues、Juliana C. Gomes、Joel Smith、Fernando Coelho

  DOI：10.1016/j.tetlet.2010.07.069

  日期：2010.9

  herein a facile and straightforward method to access 3,4-substituted tetrahydro-1,8-naphthyridines from Morita–Baylis–Hillman. The strategy is based on a tandem sequence involving a Michael addition reaction followed by an intramolecular SNAr reaction on a silylated-Morita–Baylis–Hillman adduct. In a single step, a new cycle is formed and the relative stereochemistry of two new centers is controlled

  我们在此公开了一种从Morita-Baylis-Hillman访问3,4-取代的四氢-1,8-萘啶的简便直接方法。该策略基于串联序列，该序列涉及迈克尔加成反应，然后在甲硅烷基化的Morita-Baylis-Hillman加合物上进行分子内S N Ar反应。在一个步骤中，形成一个新的循环，并以良好至优异的非对映选择性控制了两个新中心的相对立体化学。
• Design and synthesis of novel cytotoxic agents based on combined framework of quinoline and nimesulide
  作者：Lingam Venkata Reddy、Mohan Kethavath、Mamatha Nakka、Syed Sultan Beevi、Lakshmi Narasu Mangamoori、Khagga Mukkanti、Sarbani Pal

  DOI：10.1002/jhet.801

  日期：2012.1

  diverse MBH adducts was prepared via the reaction of derivatives of 2‐chloroquinoline‐3‐carbaldehyde and various activated alkenes in good yields. Many of these compounds were found to be potent when tested against human prostate cancer (Pc‐3) cell line in vitro. Among all the compounds tested N‐(2‐chloro‐3‐(2‐cyano‐1‐hydroxyallyl)‐7‐phenoxyquinolin‐6‐yl)formamide (IC50 = 1.2 μg mL−1) was identified as

  源自尼美舒利骨架的喹啉醛功能化是使用Morita–Baylis–Hillman（MBH）化学方法进行的。通过2-氯喹啉-3-甲醛的衍生物与各种活化烯烃的高收率反应，制备了许多基于喹啉的新型MBH加合物。当在体外针对人前列腺癌（Pc-3）细胞系进行测试时，发现其中许多化合物都有效。在所有测试的化合物中，N-（2-氯-3-（2-氰基-1-羟基烯丙基）-7-苯氧基喹啉-6-基）甲酰胺（IC 50 = 1.2μgmL -1）被认为是最有效的化合物在这个系列中。J.杂环化​​学。（2012）。