2-(5-Fluoro-1-benzothiophen-2-yl)acetonitrile | 139313-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(5-Fluoro-1-benzothiophen-2-yl)acetonitrile
• CAS: 139313-98-7
• 化学式: C₁₀H₆FNS
• 分子量: 191.229
• InChiKey: UFHDNJBWOAPPFS-UHFFFAOYSA-N

物化性质

• 沸点：
  343.6±27.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-Fluoro-1-benzothiophen-2-yl)acetonitrile 在 吡啶 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 3H-1,2,3,5-噁噻二唑,4-[(5-氟苯并[b]噻吩并-2-基)甲基]-,2-氧化
  参考文献：
  名称：

  Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002
• 作为产物：
  描述：

  苯并[b]噻吩,5-氟-2-甲基- 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基硫酸氢铵 作用下， 以 四氯化碳 、 氯仿 、 水 为溶剂， 反应 25.5h， 生成 2-(5-Fluoro-1-benzothiophen-2-yl)acetonitrile
  参考文献：
  名称：

  Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002

文献信息

• Studies on the structure–activity relationship of bicifadine analogs as monoamine transporter inhibitors
  作者：Mingzhu Zhang、Florence Jovic、Troy Vickers、Brian Dyck、Junko Tamiya、Jonathan Grey、Joe A. Tran、Beth A. Fleck、Rebecca Pick、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmcl.2008.05.077

  日期：2008.7

  Compounds with various activities and selectivities were discovered through structure -activity relationship studies of bicifadine analogs as monoamine transporter inhibitors. The norepinephrine-selective 2-thienyl compound S-6j was efficacious in a rodent pain model. (C) 2008 Elsevier Ltd. All rights reserved.
• Studies on a series of milnacipran analogs containing a heteroaromatic group as potent norepinephrine and serotonin transporter inhibitors
  作者：Troy Vickers、Brian Dyck、Junko Tamiya、Mingzhu Zhang、Florence Jovic、Jonathan Grey、Beth A. Fleck、Anna Aparicio、Michael Johns、Liping Jin、Hui Tang、Alan C. Foster、Chen Chen

  DOI：10.1016/j.bmcl.2008.04.045

  日期：2008.6

  A series of milnacipran analogs containing a heteroaromatic group were synthesized and studied as monoamine transporter inhibitors. Many compounds exhibited higher potency than milnacipran at NET and NET/SERT with no significant change in lipophilicity. For example, compound R-26f was about 10-fold more potent than milnacipran with IC(50) values of 8.7 and 26 nM at NET and SERT, respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides
  作者：John W. Ellingboe、Thomas R. Alessi、Terence M. Dolak、Thomas T. Nguyen、John D. Tomer、Frieda Guzzo、Jehan F. Bagli、Michael L. McCaleb

  DOI：10.1021/jm00085a002

  日期：1992.4

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).