3-methylthien-2-yl(thien-2-yl)methanone | 133374-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-methylthien-2-yl(thien-2-yl)methanone
• 英文别名: 3-methyl-2-thienyl 2-thienyl ketone；Methyl-2-thienyl 2-thienyl ketone；(3-methylthiophen-2-yl)-thiophen-2-ylmethanone
• CAS: 133374-02-4
• 化学式: C₁₀H₈OS₂
• 分子量: 208.305
• InChiKey: NPKPETNURYBOBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methylthien-2-yl(thien-2-yl)methanone 在 氢溴酸 、 potassium carbonate 、 magnesium 、 potassium iodide 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 47.5h， 生成 1-[(E)-4-(3-Methyl-thiophen-2-yl)-4-thiophen-2-yl-but-3-enyl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (Tiagabine) as an anticonvulsant drug candidate

  摘要：

  A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [H-3]-GABA uptake in rat synaptosomes was determined for each compound. It was found that the most potent examples are those having a substituent in an ''ortho'' position in one or both aromatic/heteroaromatic groups. The majority of the compounds described are structurally related to tiagabine, (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride (NNC 05-0328) and some of the reasoning behind the selection of this compound as a drug candidate is summarized.

  DOI：

  10.1021/jm00064a005
• 作为产物：
  描述：

  ethyl E/Z-(R)-1-<4-(3-methylthien-2-yl)-4-(thien-2-yl)-3-butenyl>-3-piperidinecarboxylate hydrochloride 在 盐酸 、 potassium permanganate 、 copper(II) sulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成 3-methylthien-2-yl(thien-2-yl)methanone
  参考文献：
  名称：

  Chorghade, Mukund S.; Ellegaard, Peter; Lee, Elaine C., Heterocycles, 1994, vol. 37, # 2, p. 783 - 792

  摘要：

  DOI：

文献信息

• The tris(2-thienyl)methyl cation problem. NMR spectroscopic study
  作者：Belen Abarca、Gregorio Asensio、Rafael Ballesteros、Teresa Varea

  DOI：10.1021/jo00010a011

  日期：1991.5

  A series of homologues of the trityl cation obtained by total or partial substitution of the phenyl rings for 2- or 3-thienyl groups has been studied by H-1 and C-13 NMR. In general, the spectral parameters found follow the expected trends. However, a most unexpected effect is found in the transformation of tris(2-thienyl)carbinol (1d) into tris(2-thienyl)methyl cation (2d), since the increase of the total chemical shift (DELTA-SIGMA-delta) associated with the ionization is as low as 105 ppm. To account for this observation, several hypotheses are discussed including the possibility of through-space charge delocalization by the three sulfur atoms and the interaction of the thiophene rings in an alternate conformation.
• The synthesis of novel GABA uptake inhibitors. 1. Elucidation of the structure-activity studies leading to the choice of (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid (Tiagabine) as an anticonvulsant drug candidate
  作者：Knud Erik Andersen、Claus Braestrup、Frederik C. Groenwald、Anker S. Joergensen、Erik B. Nielsen、Ursula Sonnewald、Per O. Soerensen、Peter D. Suzdak、Lars J. S. Knutsen

  DOI：10.1021/jm00064a005

  日期：1993.6

  A series of different synthetic approaches to novel GABA uptake inhibitors are described, leading to examples which are derivatives of nipecotic acid and guvacine, substituted at nitrogen by 4,4-diaryl-3-butenyl or 2-(diphenylmethoxy)ethyl moieties. The in vitro value for inhibition of [H-3]-GABA uptake in rat synaptosomes was determined for each compound. It was found that the most potent examples are those having a substituent in an ''ortho'' position in one or both aromatic/heteroaromatic groups. The majority of the compounds described are structurally related to tiagabine, (R)-1-[4,4-bis(3-methyl-2-thienyl)-3-butenyl]-3-piperidinecarboxylic acid hydrochloride (NNC 05-0328) and some of the reasoning behind the selection of this compound as a drug candidate is summarized.
• Chorghade, Mukund S.; Ellegaard, Peter; Lee, Elaine C., Heterocycles, 1994, vol. 37, # 2, p. 783 - 792
  作者：Chorghade, Mukund S.、Ellegaard, Peter、Lee, Elaine C.、Petersen, Hans、Soerensen, Per Olaf

  DOI：——

  日期：——