3-Thienyl-3'-pyridyl ketone | 21314-78-3

• 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-Thienyl-3'-pyridyl ketone
• 英文别名: pyridin-3-yl(thiophen-3-yl)methanone
• CAS: 21314-78-3
• 化学式: C₁₀H₇NOS
• 分子量: 189.238
• InChiKey: WZUDTTKTEIYYKN-UHFFFAOYSA-N

物化性质

• 熔点：
  72-74 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  330.1±17.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Thienyl-3'-pyridyl ketone 在 palladium on activated charcoal 盐酸 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 乙酸乙酯 为溶剂， -20.0~20.0 ℃ 、206.84 kPa 条件下， 反应 4.0h， 生成 3-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-(thiophen-3-yl)ethyl]pyridine
  参考文献：
  名称：

  Imidazolines as efficacious glucose-dependent stimulators of insulin secretion

  摘要：

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00041-2
• 作为产物：
  描述：

  Pyridin-3-yl(thiophen-3-yl)methanol 生成 3-Thienyl-3'-pyridyl ketone
  参考文献：
  名称：

  SHINJI, TERAO;KOBEI, NISHIKAWA

  摘要：

  DOI：

文献信息

• 2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
  作者：Seung-Hoi Kim、Reuben D. Rieke

  DOI：10.1016/j.tet.2010.02.061

  日期：2010.4

  A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.

  已证明使用Rieke锌分别与2-溴吡啶和3-溴吡啶直接合成2-吡啶基和3-吡啶基锌溴化物的简便合成方法。各种不同的亲电试剂已与所得的有机锌试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。
• A Facile Synthetic Approach to the Preparation of 3-Pyridyl Derivatives: Preparations and Coupling Reactions of 3-Pyridylzinc and Its Analogues
  作者：Reuben Rieke、Seung-Hoi Kim、Tim Slocum

  DOI：10.1055/s-0029-1217000

  日期：2009.11

  A facile synthetic approach to the direct preparation of 3-pyridylzinc bromide has been demonstrated using Rieke zinc with 3-bromopyridine in the presence of a catalytic amount of lithium chloride. A variety of different electrophiles have been coupled to give the corresponding cross-coupling products in moderate to good yields. Also, this methodology has been expanded to the preparation of the corresponding

  已经证明在催化量的氯化锂的存在下，使用里克锌和3-溴吡啶，可以直接合成3-吡啶基溴化锌的简便合成方法。已经将多种不同的亲电试剂偶联，以中等至良好的产率得到相应的交叉偶联产物。同样，该方法已扩展到制备3-溴吡啶类似物的相应有机锌试剂。 3-吡啶基溴化锌-偶联反应-杂环衍生物
• A General Synthesis of Diarylketones by Means of a Three-Component Cross-Coupling of Aryl and Heteroaryl Bromides, Carbon Monoxide, and Boronic acids
  作者：Helfried Neumann、Anne Brennführer、Matthias Beller

  DOI：10.1002/chem.200800001

  日期：2008.4.18

  Pd(OAc)2/di-1-adamantyl-n-butylphosphine (cataCXium A) is highly active in the three-component Suzuki carbonylation and represents the most general catalyst system reported up to now. A broad range of aryl/heteroaryl bromides and aryl boronic acids can be coupled to the corresponding diarylketones at low catalyst loadings.

  Pd（OAc）2 /二-1-金刚烷基-正丁基膦（cataCXium A）在三组分铃木羰基化反应中具有很高的活性，是迄今为止报道的最通用的催化剂体系。各种各样的芳基/杂芳基溴化物和芳基硼​​酸可以在低催化剂负载下与相应的二芳基酮偶联。
• Ligand-Free Pd-Catalyzed Carbonylative Cross-Coupling Reactions under Atmospheric Pressure of Carbon Monoxide: Synthesis of Aryl Ketones and Heteroaromatic Ketones
  作者：Hongling Li、Min Yang、Yanxing Qi、Jijun Xue

  DOI：10.1002/ejoc.201001685

  日期：2011.5

  The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd 2 (dba) 3 as a ligand-free catalyst under atmospheric pressure of carbon monoxide has been firstly developed. Under mild reaction conditions, a broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent

  Pd 2 (dba) 3 作为无配体催化剂，在一氧化碳常压下，硼酸与芳基碘化物的羰基化铃木交叉偶联反应已被首次开发。在温和的反应条件下，广泛的芳基/杂芳基碘化物和芳基/杂芳基硼酸被选择性偶联以在低催化剂负载量（0.05至2mol%）下以良好至优异的产率提供相应的二芳基酮。此外，催化剂还可以循环使用。
• Oral hypoglycaemic agents
  申请人：——

  公开号：US20020132812A1

  公开（公告）日：2002-09-19

  Compounds of formula (I) which are optionally substituted 2-(&ohgr;,&ohgr;-diarylalkyl)-4,5-dihydro-1H-imidazoles and 2-(&ohgr;,&ohgr;-diarylalkyl)-1,4,5,6-tetrahydropyrimidines and salts thereof with inorganic and organic acids have interesting pharmacological properties. Thus, the compounds are useful in the treatment of type 2 diabetes.

  式(I)的化合物，它们是可选择取代的2-(&ohgr;，&ohgr;-二芳基烷基)-4,5-二氢-1H-咪唑和2-(&ohgr;，&ohgr;-二芳基烷基)-1,4,5,6-四氢嘧啶及其与无机和有机酸的盐具有有趣的药理特性。因此，这些化合物在治疗2型糖尿病方面是有用的。