3-(2,4-dichlorophenyl)-3-oxo-N-phenyl-propanethioanilide | 1010728-53-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,4-dichlorophenyl)-3-oxo-N-phenyl-propanethioanilide
• 英文别名: β-(2,4-dichlorobenzoyl)thioacetanilide；3-(2,4-dichlorophenyl)-3-oxo-N-phenylpropanethioamide
• CAS: 1010728-53-6
• 化学式: C₁₅H₁₁Cl₂NOS
• 分子量: 324.23
• InChiKey: DLCDYVZDWNLYDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-(2,4-dichlorophenyl)-3-oxo-N-phenyl-propanethioanilide 、 (Z)-4-(2-fluorobenzylidene)-2-phenyloxazol-5(4H)-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到N-[8-chloro-4-(2-fluorophenyl)-2,5-dioxo-1-phenyl-2,3,4,5-tetrahydro-1H-thiochromeno[2,3-b]pyridin-3-yl]benzamide
  参考文献：
  名称：

  β-（2-氯代芳酰基）硫代乙酰苯胺在合成中的应用：硫铬色素[2,3- b ]吡啶衍生物的不寻常且高效的获得

  摘要：

  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。

  DOI：

  10.1021/jo7024702

文献信息

• Application of ortho-chloro-β-aroylthioamides in synthesis(II): an efficient one-pot, three-component synthesis of tricyclic thiochromeno[2,3-b]pyridine derivatives
  作者：Li-Rong Wen、Chen Ji、Ming Li、Huai-Yuan Xie

  DOI：10.1016/j.tet.2008.12.057

  日期：2009.2

  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.
• Reactivity of Functionalized <i>N</i>,<i>S</i>-Ketene Acetal: Regioselective Construction of Tetrahydrobenzo[<i>b</i>]pyran and Chromeno[2,3-<i>b</i>]quinoline Derivatives
  作者：Ming Li、Yan-Li Hou、Li-Rong Wen、Fu-Meng Gong

  DOI：10.1021/jo101902z

  日期：2010.12.17

  Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multi-component reactions (MCRs) and tandem [3 + 3] annulations of beta-benzoylthioacetanilides or beta-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethy1-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular SNAr in the presence of K2CO3 led to an unprecedented novel chromeno-[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.
• 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.
• 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。