2-氯-8-甲氧基喹啉-3-甲醛 | 73568-28-2

• 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
• 中文名称: 2-氯-8-甲氧基喹啉-3-甲醛
• 英文名称: 2-chloro-8-methoxyquinoline-3-carbaldehyde
• CAS: 73568-28-2
• 化学式: C₁₁H₈ClNO₂
• 分子量: 221.643
• InChiKey: TWGAHTGLODITOW-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C
• 沸点：
  373.9±37.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-氯-8-甲氧基喹啉-3-甲醛 在 盐酸 、 sodium sulfide 作用下， 以 乙醇 为溶剂， 以85%的产率得到8-methoxy-3-formyl-2-mercaptoquinoline
  参考文献：
  名称：

  A Fast and Large-Scale Synthesis of 3-Formyl-2-mercaptoquinolines

  摘要：

  A convenient, efficient, and inexpensive procedure for the synthesis of 3-formyl-2-mercaptoquinolines 2a-l has been developed by a simple one-pot reaction of 3-formyl-2-chloroquinolines 1a-l with sodium sulfide and hydrochloric acid in ethanol. The structures of all the synthesized compounds were elucidated on the basis of elemental analyses and IR, H-1 NMR, and mass spectral data.

  DOI：

  10.1080/10426500600574796
• 作为产物：
  描述：

  2-甲氧基-6-甲基苯胺 在 溶剂黄146 、 三氯氧磷 作用下， 反应 16.5h， 生成 2-氯-8-甲氧基喹啉-3-甲醛
  参考文献：
  名称：

  Synthesis of indenoquinolinone through aryne-mediated Pd(II)-catalysed remote C–H activation

  摘要：

  Indenoquinolinones是通过Pd介导的同时C–H（醛）和C–X键活化，从2-卤代喹啉-3-羧醛合成的。进行了DFT研究以探讨机制路径，原位UV-Vis研究表明存在Pd(II)中间体物种。与Aryne结合的Pd复合物是这些反应中的实际中间体。反应性Aryne与Pd的结合降低了副反应的可能性。

  DOI：

  10.1007/s11164-020-04387-2

文献信息

• Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines
  作者：Aleksandr N. Shestakov、Alena S. Pankova、Mikhail A. Kuznetsov

  DOI：10.1007/s10593-017-2179-5

  日期：2017.10

  Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]-acridines. Substituent at the triple bond governs a choice between transition metal or Brønsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the o-aryl(phenylethynyl) fragment. PtCl2 efficiently

  3-炔基-2-芳基吡啶和喹啉的环异构化为苯并[ h ]喹啉和苯并[ c ] -ac啶提供了一种直接的方法。在三键处的取代基决定过渡金属催化或布朗斯台德酸催化之间的选择。三氟甲磺酸的直接亲电子活化引起邻-芳基（苯基乙炔基）片段的几乎定量环化。PtCl 2有效催化2-芳基-3-乙炔基戊烯的环化。
• Synthesis of novel nitrogen containing naphtho[2,1-b]furan derivatives and investigation of their anti microbial activities
  作者：Gundibasappa K. Nagaraja、Gowdara K. Prakash、Marlingaplara N. Kumaraswamy、Vijayavittala P. Vaidya、Kittappa M. Mahadevan

  DOI：10.3998/ark.5550190.0007.f19

  日期：——

  Ethyl naphtho(2,1-b)furan-2-carboxylate has been prepared from 2-hydroxy-1- naphthaldehyde 1 and ethyl chloroacetate, which on further treatment with hydrazine hydrate gave naphtha(2,1- b)furan-2-carbohydrazide 3. The resulting compound 3 was treated with substituted aldehydes of 2-chloro-3-formylquinolines to give the Schiff base, which on treatment with chloro acetyl chloride gave the title compounds

  萘并（2,1-b）呋喃-2-羧酸乙酯已由 2-羟基-1-萘醛 1 和氯乙酸乙酯制备，再用水合肼进一步处理得到石脑油（2,1-b）呋喃-2-碳酰肼3。所得化合物3用2-氯-3-甲酰基喹啉的取代醛处理得到席夫碱，其用氯乙酰氯处理得到标题化合物。化合物的结构已通过元素分析和光谱研究得到证实。筛选合成的化合物的抗菌和抗真菌活性。
• Enantioselective Synthesis of Substituted 3-Quinolyl Alkanols and Their Application to Asymmetric Autocatalysis
  作者：Kenso Soai、Itaru Sato、Tomohiko Nakao、Rie Sugie、Tsuneomi Kawasaki

  DOI：10.1055/s-2004-822402

  日期：——

  Enantioenriched 3-quinolyl alkanols act as asymmetric autocatalysts in the addition of diisopropylzinc to the corresponding substituted quinoline-3-carbaldehydes, to afford themselves with an amplified enantiomeric excess(ee) of up to 97%.

  对映体富集的 3-喹啉链烷醇在将二异丙基锌添加到相应的取代的 quinoline-3-carbaldehydes 时充当不对称自催化剂，使其自身具有高达 97% 的放大对映体过量 (ee)。
• CAN Mediated Mechanochemical Synthesis of Substituted Pyridine Derivatives
  作者：Radhika Khanna、Aarti Dalal、Kulbir Kadyan、Ramesh Kumar、Parvin Kumar、Ramesh C. Kamboj

  DOI：10.2174/1570178615666180102153707

  日期：2018.7.2

  A simple, green and cost-effective protocol has been devised for the synthesis of 4-substituted-2,6-dimethyl-3,5-pyridinecarboxylates from Hantzsch-type 1,4-dihydropyridines via rapid oxidation in excellent yields using 1.5 equivalent of ceric ammonium nitrate within 15 minutes in solvent-free conditions. The method was able to furnish the products in excellent yields. The products obtained were characterized by their NMR and melting points data.

  一种简便、绿色且经济的合成方法已被设计出来，用于从汉奇型1,4-二氢吡啶通过快速氧化合成4-取代-2,6-二甲基-3,5-吡啶羧酸盐，使用1.5当量的硝酸铈铵在无溶剂条件下15分钟内实现优异的产率。该方法能够以优异的产率提供产物。所得产物通过其核磁共振和熔点数据进行表征。
• Na₂S-mediated synthesis of terminal alkynes from <i>gem</i>-dibromoalkenes
  作者：Radhey M. Singh、Durgesh Nandini、Kishor Chandra Bharadwaj、Tanu Gupta、Raj Pal Singh

  DOI：10.1039/c7ob02431b

  日期：——

  The Na2S-mediated facile synthesis of terminal alkynes from gem-dibromoalkenes, at 20/40 °C under open flask conditions has been developed. Various precursors derived from heteroaromatic/aromatic/aliphatic aldehydes were found compatible. The reaction is proposed to proceed through the Fritsch–Buttenberg–Wiechell (FBW) rearrangement involving the corresponding vinyl carbene. Using mild reaction conditions

  已经开发了Na 2 S介导的在开放烧瓶条件下，由宝石-二溴代烯烃容易地合成末端炔烃的方法。发现衍生自杂芳族/芳族/脂族醛的各种前体是相容的。建议通过涉及相应乙烯基卡宾的Fritsch-Buttenberg-Wiechell（FBW）重排进行反应。与较早的路线相比，在空气气氛下使用温和的反应条件和廉价的Na 2 S·9H 2 O会具有明显的优势。