3-(2,5-dichlorophenyl)-3-oxo-N-phenylpropanethioamide | 1010728-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2,5-dichlorophenyl)-3-oxo-N-phenylpropanethioamide
• CAS: 1010728-54-7
• 化学式: C₁₅H₁₁Cl₂NOS
• 分子量: 324.23
• InChiKey: PBUKXFPKBNBXHR-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-(2,5-dichlorophenyl)-3-oxo-N-phenylpropanethioamide 、 (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80%的产率得到N-[7-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.
• 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。