1-anilino-2-phenylthiocarbamoylcyclopent-1-ene | 1157-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-anilino-2-phenylthiocarbamoylcyclopent-1-ene
• 英文别名: 1-Anilino-2-phenylthiocarbamoyl-cyclopent-1-en；1-Anilino-cyclopenten-2-thiocarbonsaeureanilid；Thioharnstoff；2-Anilino-N-phenylcyclopent-1-ene-1-carbothioamide；2-anilino-N-phenylcyclopentene-1-carbothioamide
• CAS: 1157-73-9
• 化学式: C₁₈H₁₈N₂S
• 分子量: 294.42
• InChiKey: ZTHQEYOOUFONLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-1-deoxy-1-(1,3-dimethyl-2,4,6-trioxo-1H,3H,5H-pyrimidin-5-ylidene)-l-arabinitol 、 1-anilino-2-phenylthiocarbamoylcyclopent-1-ene 以 二氯甲烷 为溶剂， 反应 72.0h， 以76%的产率得到(1'S,2'R,3'S)-5-(1',2',3',4'-tetra-O-acetylbutane-1',2',3',4'-tetraolyl)-1,3-dimethyl-8a-anilino-5a-(N-phenylthiocarbamoyl)-1,2,3,4,5a,8a-hexahydro-5H-cyclopentano[6,5]pyrano[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Application of dimedone enamines as dienophiles: stereoselective synthesis of amino enols of fused uracils containing a sugar moiety by hetero-Diels–Alder reactions of barbituric acid 5-ylidene alditols with dimedone enamines

  摘要：

  Dimedone enamines were applied for the first time as new dienophiles in hetero-Diels-Alder reactions with inverse electron demand. Cycloadditions of barbituric acid 5-ylidene alditols with dimedone enamines were performed in dichloromethane at room temperature for 3 days and fused uracils-chromeno[2,3-d]pyrimidine-2,4-diones were obtained in good 73-87% yields. Only one enantiomerically pure stereoisomer was obtained in each studied cycloaddition. Analysis of H-1 NMR and 2D NMR spectra allowed for the determination that cycloadducts exist in solution as mixture of the neutral form and dipolar ion. The prepared fused uracils contain both amine and enol functional groups, so share amphiprotic properties and they are zwitterions in solid state. The new class of compounds-amino enols was synthesized, which similarly to amino acids exists as zwitterions. In obtained cycloadducts amino groups and sugar moieties are close each other and they both are in cis configuration and in axial position. It was also shown that different alkenes can be used as dienophiles towards barbituric acid 5-ylidene alditols, for example, styrene or 1-amino-2-thiocarbamoyi-cyclopent-1-ene. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.065
• 作为产物：
  描述：

  2-Hydroxycyclopenten-(1)-thiocarbonsaeure-anilid 、 苯胺 以 苯 为溶剂， 生成 1-anilino-2-phenylthiocarbamoylcyclopent-1-ene
  参考文献：
  名称：

  Walter,W.; Fleck,T., Justus Liebigs Annalen der Chemie, 1976, p. 670 - 704

  摘要：

  DOI：

文献信息

• WALTER W.; FLECK T., J. LIEBIGS ANN. CHEM. <JLAC-BF>, 1976, NO 4, 670-681
  作者：WALTER W.、 FLECK T.

  DOI：——

  日期：——
• Walter,W.; Fleck,T., Justus Liebigs Annalen der Chemie, 1976, p. 670 - 704
  作者：Walter,W.、Fleck,T.

  DOI：——

  日期：——
• Application of dimedone enamines as dienophiles: stereoselective synthesis of amino enols of fused uracils containing a sugar moiety by hetero-Diels–Alder reactions of barbituric acid 5-ylidene alditols with dimedone enamines
  作者：Aleksandra Pałasz、Dariusz Cież、Bogdan Musielak、Justyna Kalinowska-Tłuścik

  DOI：10.1016/j.tet.2015.09.065

  日期：2015.11

  Dimedone enamines were applied for the first time as new dienophiles in hetero-Diels-Alder reactions with inverse electron demand. Cycloadditions of barbituric acid 5-ylidene alditols with dimedone enamines were performed in dichloromethane at room temperature for 3 days and fused uracils-chromeno[2,3-d]pyrimidine-2,4-diones were obtained in good 73-87% yields. Only one enantiomerically pure stereoisomer was obtained in each studied cycloaddition. Analysis of H-1 NMR and 2D NMR spectra allowed for the determination that cycloadducts exist in solution as mixture of the neutral form and dipolar ion. The prepared fused uracils contain both amine and enol functional groups, so share amphiprotic properties and they are zwitterions in solid state. The new class of compounds-amino enols was synthesized, which similarly to amino acids exists as zwitterions. In obtained cycloadducts amino groups and sugar moieties are close each other and they both are in cis configuration and in axial position. It was also shown that different alkenes can be used as dienophiles towards barbituric acid 5-ylidene alditols, for example, styrene or 1-amino-2-thiocarbamoyi-cyclopent-1-ene. (C) 2015 Elsevier Ltd. All rights reserved.