3-(2,4-difluorophenyl)-3-oxo-N-phenylpropanethioamide | 1010728-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,4-difluorophenyl)-3-oxo-N-phenylpropanethioamide
• CAS: 1010728-83-2
• 化学式: C₁₅H₁₁F₂NOS
• 分子量: 291.321
• InChiKey: IVPLWAXNSIRFMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙二酸环(亚)异丙酯 、 3-(2,4-difluorophenyl)-3-oxo-N-phenylpropanethioamide 、 2,5-二氯苯甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以70%的产率得到4-(2,5-dichlorophenyl)-8-fluoro-1-phenyl-3,4-dihydro-1H-thiochromeno[2,3-b]pyridine-2,5-dione
  参考文献：
  名称：

  Application of ortho-chloro-β-aroylthioamides in synthesis(II): an efficient one-pot, three-component synthesis of tricyclic thiochromeno[2,3-b]pyridine derivatives

  摘要：

  Tricyclic thiochromeno[2,3-b]pyridine derivatives have been successfully synthesized in an unusual one-pot multicomponent cascade reaction from ortho-halo-beta-aroylthioamides, Meldrum's acid, and aromatic aldehydes. The reaction presumably proceeds via Knoevenagel condensation-Michael addition-cyclo-condensation-decarboxylation-rearrangement-intramolecular SNAr reaction sequence. High bond forming efficiency of this reaction makes it attractive for the synthesis of thiochromeno[2,3-b]pyridine derivatives in a single step operation. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.12.057

文献信息

• Application of β-(2-Chloroaroyl) Thioacetanilides in Synthesis:  An Unusual and Highly Efficient Access to Thiochromeno[2,3-<i>b</i>]pyridine Derivatives
  作者：Li-Rong Wen、Ji-Hui Sun、Ming Li、En-Tao Sun、Shu-Sheng Zhang

  DOI：10.1021/jo7024702

  日期：2008.3.1

  A series of unusual fused tricyclic thiochromeno[2,3-b]pyridines were successfully synthesized by tandem [3 + 3] annulation and SNAr of β-(2-chloroaroyl) thioacetanilides with activated 4-arylidene-2-phenyloxazol-5(4H)-ones or aromatic aldehydes and ethyl 2-cyanoacetate under microwave irradiation, respectively. Because of the existence of the o-chloro atom of β-(2-chloroaroyl) thioacetanilides, these

  稠合三环一系列的异常thiochromeno [2,3- b ]吡啶化合物成功地被串联合成[3 + 3]环和S Ñ β-（2- chloroaroyl）与活化的4-芳亚甲基-2-苯基恶唑5 thioacetanilides的氩在微波辐射下分别为（4 H）-一或芳族醛和2-氰基乙酸乙酯。因为o的存在β-（2-氯代芳酰基）硫代乙酰胺基的-氯原子，这些反应非常温和，方便且邻位选择性，可形成新的稠合三环靶分子。在多米诺骨牌过程中，至少涉及七个反应性不同的化学位点，并且最多生成三个新的共价键和一个仅具有顺式构型的三环。提出了有关这些转换的综合研究和机制建议。
• Three-Component Cascade Annulation of β-Ketothioamides Promoted by CF₃CH₂OH: A Regioselective Synthesis of Tetrasubstituted Thiophenes
  作者：Li-Rong Wen、Tao He、Ming-Chao Lan、Ming Li

  DOI：10.1021/jo401397d

  日期：2013.11.1

  A rapid and highly efficient method for the regioselective synthesis of thiophene derivatives has been developed by annulation of β-ketothioamides with arylglyoxals and 5,5-dimethyl-1,3-cyclohexanedione in CF3CH2OH within 15 min. The present synthesis has several desirable features, such as high regioselectivity, a concise one-pot protocol, short reaction time, and easy purification. This methodology

  通过在15分钟内在CF 3 CH 2 OH中将β-酮硫酰胺与芳基乙二醛和5,5-二甲基-1,3-环己二酮环化，已开发出一种快速高效的噻吩衍生物的区域选择性合成方法。本合成具有几个理想的特征，例如高区域选择性，简洁的一锅操作方案，短的反应时间和易于纯化。该方法学提供了另一种方法，可通过一锅级联反应轻松获得四取代的噻吩，而无需其他添加剂。
• Modulating the Reactivity of Functionalized <i>N</i>,<i>S</i>-Ketene Acetal in MCR: Selective Synthesis of Tetrahydropyridines and Thiochromeno[2,3-<i>b</i>]pyridines via DABCO-Catalyzed Tandem Annulation
  作者：Li-Rong Wen、Yong-Jie Shi、Guang-Yuan Liu、Ming Li

  DOI：10.1021/jo202665q

  日期：2012.5.4

  An efficient and straightforward three-component synthetic protocol was developed to synthesize 1,2,3,4-tetrahydropyridine derivatives or thiochromeno[2,3-b]pyridine derivatives from beta-aroylthioacetanilides or beta-(2-haloaroyl)thioacetanilides, aldehydes, and aroyl acetonitriles via DABCO-catalyzed tandem [3 + 2 + 1] annulation and SNAr reaction. This synthetic approach has the prominent features of high chemo-, stereo- (or enantio-), and unusual regioselectivity. In the domino processes, at least seven reactive sites were involved, and up to three covalent bonds and one functionalized pyridine ring were generated. This facile and efficient reaction is a quite general for the preparation of tetrahydropyridine derivatives or thiochromeno[2,3-b]pyridine derivatives.