7-chloro-3-formyl-2-mercaptoquinoline

• 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: 7-chloro-3-formyl-2-mercaptoquinoline
• 英文别名: 7-chloro-2-mercapto-quinoline-3-carbaldehyde；7-chloro-2-sulfanylidene-1H-quinoline-3-carbaldehyde
• 化学式: C₁₀H₆ClNOS
• 分子量: 223.683
• InChiKey: YXWQDRJSJJWLRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-3-formyl-2-mercaptoquinoline 在 一水合肼 作用下， 生成 7-chloro-3-(hydrazineylidenemethyl)quinoline-2-thiol
  参考文献：
  名称：

  Synthesis of Quinoline-Based Thieno-Seleno-Phenylquinazolinones

  摘要：

  The synthesis of quinoline-substituted phenylquinazolinones containing sulfur and selenium is described. These molecules were isolated from a series of reactions of 2-phenyl-4H-3,1-benzoxazin-4-one with 2-chloro, 2-thieno, and 2-selenoquinoline-3-carbaldehyde hydrazones. The structure of the isolated compounds has been elucidated on the basis of IR, 1H NMR, mass spectral, and elemental analysis data.

  DOI：

  10.1080/10426500802176945
• 作为产物：
  描述：

  2,7-二氯喹啉-3-羧醛 在 sodium sulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-chloro-3-formyl-2-mercaptoquinoline
  参考文献：
  名称：

  通过多米诺·迈克尔加成/环化反应快速，清洁，高效地一锅合成噻喃并[2,3- b ]喹啉

  摘要：

  从3-甲酰基-喹啉-2-硫酮与丙烯腈在室温下使用经济的有机碱Et 3 N反应，可以快速高效地一锅合成噻吩并[2,3- b ]喹啉。该反应通过多米诺骨牌迈克尔加成/环化反应顺利进行，不需要干燥溶剂，惰性气氛和柱色谱法纯化。

  DOI：

  10.1016/j.tetlet.2012.04.032

文献信息

• Enantioselective Organocatalytic Domino Michael/Aldol Reactions: An Efficient Procedure for the Stereocontrolled Construction of 2<i>H</i>-Thiopyrano[2,3-b]quinoline Scaffolds
  作者：Lulu Wu、Youming Wang、Haibin Song、Liangfu Tang、Zhenghong Zhou、Chuchi Tang

  DOI：10.1002/asia.201300450

  日期：2013.9

  An efficient procedure for the stereocontrolled construction of 2H‐thiopyrano[2,3‐b]quinoline scaffolds has been developed, starting from simple compounds. The domino Michael/aldol reactions between 2‐mercaptobenzaldehydes and enals, promoted by chiral diphenylprolinol TMS ether, proceed with excellent chemo‐ and enantioselectivity to give the corresponding synthetically useful and pharmaceutically

  从简单的化合物开始，已经开发出了一种有效的立体控制2 H -thiopyrano [2,3-b]喹啉骨架的方法。手性二苯基脯氨醇TMS醚促进的2-巯基苯甲醛与烯醛之间的多米诺米歇尔/羟醛反应，具有出色的化学和对映选择性，可提供相应的合成上有用的和药学上有价值的2 H-硫代吡喃并[2,3-b]喹啉ee的产率为90–99％。
• Synthesis of Optically Active 2<i>H</i>-Thiopyrano[2,3-<i>b</i>]quinolines with Three Contiguous Stereocenters<i>via</i>an Organocatalytic Asymmetric Tandem Michael-Henry Reaction
  作者：Lulu Wu、Youming Wang、Haibin Song、Liangfu Tang、Zhenghong Zhou、Chuchi Tang

  DOI：10.1002/adsc.201300086

  日期：2013.4.15

  Optically active 2H‐thiopyrano[2,3‐b]quinolines with three contiguous stereocenters have been synthesized via a chiral bifunctional squaramide‐catalyzed tandem Michael–Henry reaction between 2‐mercaptoquinoline‐3‐carbaldehydes and nitroolefins. The reactions proceed with excellent diastereo‐ and enantioselectivity to give the title compounds in high yields with high levels of diastereo‐ and enantioselectivity

  光学活性的2 H-硫代吡喃并[2,3- b ]喹啉具有三个连续的立体中心，是通过2-巯基喹啉-3-甲醛与硝基烯烃之间的手性双官能方酰胺催化的迈克尔-亨利串联反应合成的。反应以极好的非对映和对映选择性进行，以高收率得到标题化合物，同时具有高水平的非对映和对映选择性（分别高达> 99/1 dr和> 99％ee）。
• Organocatalyzed Highly Diastereo- and Enantioselective Tandem Sulfa-Michael-Mannich Reaction of 2-Mercaptoquinoline-3-carbaldimines with Maleimides
  作者：Lulu Wu、Youming Wang、Haibin Song、Liangfu Tang、Zhenghong Zhou、Chuchi Tang

  DOI：10.1002/cctc.201300993

  日期：2014.2

  A highly diastereo‐ and enantioselective organocatalyzed domino sulfa‐Michael–Mannich reaction of 2‐mercaptoquinoline‐3‐carbaldimines with maleimides has been developed. This approach provides a convenient and efficient access to multifuntionalized tetracyclic quinoline derivatives with three contiguous stereocenters in high yield with excellent stereoselectivity (up to >99:1 dr and >99 % ee).

  已经开发了2-巯基喹啉-3-咔二胺与马来酰亚胺的高度非对映和对映选择性的有机催化多米诺磺胺-迈克尔-曼尼希反应。这种方法可方便高效地获得具有三个连续立体中心的多官能化四环喹啉衍生物，且具有出色的立体选择性（高达> 99：1 dr和> 99％ee）。
• A glycerol mediated domino reaction: an efficient, green synthesis of polyheterocycles incorporating a new thiochromeno[2,3-b]quinoline unit
  作者：Narsidas J. Parmar、Hitesh A. Barad、Balvantsingh M. Labana、Rajni Kant、Vivek K. Gupta

  DOI：10.1039/c3ra43205j

  日期：——

  One-pot synthesis of some polyheterocycles, all of which incorporate a new thiochromeno[2,3-b]quinoline unit, has been demonstrated via a domino/Knoevenagel–hetero-Diels–Alder (DKHDA) reaction, which combines a typical aldehyde substrate, 2-methyl-2-(4-methylpent-3-en-1-yl)-2H-thiopyrano[2,3-b]quinoline-3-carbaldehyde derived from 2-mercapto-quinoline-3-carbaldehyde and citral, with 5-pyrazolone, in glycerol. As evidenced by TLC (thin layer chromatography), all the new quinoline-based aldehyde substrates can be assembled with pyrazolone in a new environmentally benign glycerol as the reaction medium without a catalyst at 120 °C. The cis-fusion between the pyran and central carbocyclic (of thiochromeno) rings in all the new polyheterocycles was confirmed from both 2D NMR experiments – COSY and NOESY – and single crystal X-ray diffraction data.

  通过多米诺/Knoevenagel-杂环-Diels-Alder（DKHDA）反应，展示了一锅合成一些多杂环化合物的方法，这些化合物均包含一个新的噻吩克酮[2,3-b]喹啉单元。该反应结合了一种典型的醛基底物，即来源于2-巯基喹啉-3-醛和香叶醇的2-甲基-2-(4-甲基戊-3-烯-1-基)-2H-噻吩吡喃[2,3-b]喹啉-3-醛，与5-吡唑酮在甘油中反应。薄层色谱（TLC）证实，所有的新型基于喹啉的醛基底物均可在新的环保溶剂甘油中，在无催化剂的条件下与吡唑酮反应，反应温度为120°C。所有新多杂环化合物中，吡喃环和中央碳环（噻吩克酮）的顺式结合通过二维核磁共振实验（COSY和NOESY）以及单晶X射线衍射数据得到了证实。
• A chitosan <i>N</i>‐ium acetate catalyzed <scp>Michael‐aldol‐dehydration‐imino‐Diels‐Alder</scp> reaction: One‐pot synthesis of new angular acridine‐fused heterocycles
  作者：Hiralben D. Atara、Gaurangkumar C. Brahmbhatt、Vishalkumar M. Parmar、Avinashkumar A. Barot、Tushar R. Sutariya、Narsidas J. Parmar

  DOI：10.1002/jhet.4696

  日期：2023.9

  A highly efficient domino protocol, Michael-aldol-dehydration-imino-Diels-Alder (MAD-IDA) reaction, that allows the intermediate MAD to combine effectively with the arylamine released from the slow reduction of nitroarene via IDA reaction has been described and several new V-shaped acridine-heterocycles have been synthesized after stirring 2-mercapto-quinoline-carbaldehydes/2-mercapto-pyridine car

  一种高效的多米诺骨牌方案，即迈克尔-醛醇-脱水-亚氨基-狄尔斯-阿尔德 (MAD-IDA) 反应，该反应允许中间体 MAD 与通过 IDA 反应缓慢还原硝基芳烃所释放的芳胺有效结合，并且已经描述了几种将2-巯基喹啉甲醛/2-巯基吡啶甲醛/2-羟基萘醛、柠檬醛/巴豆醛和NaSH在壳聚糖醋酸鎓水溶液中搅拌后合成了新的V型吖啶杂环在室温下。通过二维核磁共振实验和密度泛函理论水平计算证实了反应的立体和区域选择性。