5-(三正丁基锡)嘧啶 | 155191-68-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-(三正丁基锡)嘧啶
• 中文别名: 2-氯-5-(三丁基锡基)嘧啶；5 - (三正丁基锡)嘧啶
• 英文名称: 2-chloro-5-tributylstannanylpyrimidine
• 英文别名: 2-Chloro-5-(tributylstannyl)pyrimidine；tributyl-(2-chloropyrimidin-5-yl)stannane
• CAS: 155191-68-7
• 化学式: C₁₆H₂₉ClN₂Sn
• 分子量: 403.583
• InChiKey: JEHJKYNDOIGAEA-UHFFFAOYSA-N

物化性质

• 沸点：
  425.7±37.0 °C(Predicted)
• 密度：
  1.222 g/mL at 25 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  5-溴-2-碘嘧啶 、 5-(三正丁基锡)嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以17%的产率得到5-bromo-2'-chloro-[2,5']bipyrimidinyl
  参考文献：
  名称：

  Inversion of the Rectifying Effect in Diblock Molecular Diodes by Protonation

  摘要：

  A new molecular diode based on biphenyl-co-bispyrimidine was synthesized and showed a pronounced rectifying effect. Further studies indicate that protonation on the nitrogen atoms of the diode molecule by strong acids can reversibly alter the rectifying direction. This phenomenon can be envisioned as a starting point for single molecule detection devices.

  DOI：

  10.1021/ja051332c

文献信息

• 3D QSAR Analyses-Guided Rational Design of Novel Ligands for the (α4)₂(β2)₃ Nicotinic Acetylcholine Receptor
  作者：Holger Gohlke、Simone Schwarz、Daniela Gündisch、Maria Cristina Tilotta、Alexander Weber、Thomas Wegge、Gunther Seitz

  DOI：10.1021/jm020859m

  日期：2003.5.1

  Three-dimensional quantitative structure-activity relationship methods, the comparative molecular field analysis (CoMFA) and the comparative molecular similarity indices analysis (CoMSIA), were applied using a training set of 45 ligands of the (alpha4)(2)(beta2)(3) nicotinic acetylcholine receptor (nAChR). All compounds are related to (-)-epibatidine, (-)-cytisine, (+)-anatoxin-a, and (-)-ferruginine, and additionally, novel diazabicyclo[4.2.1]nonane- and quinuclidin-2-ene-based structures were included. Their biological data have been determined by utilizing the same experimental protocol. Statistically reliable models of good predictive power (CoMFA r(2) = 0.928, q(2) = 0.692, no. of components = 3; CoMSIA r(2) = 0.899, q(2) = 0.701, no. of components = 3) were achieved. The results obtained were graphically interpreted in terms of field contribution maps. Hence, physicochemical. determinants of binding, such as steric and electrostatic and, for the first time, hydrophobic, hydrogen bond donor, and hydrogen bond acceptor properties, were mapped back onto the molecular structures of a set of nAChR modulators. In particular, changes in the binding affinity of the modulators as a result of modifications in the aromatic ring systems could be rationalized by the steric, electrostatic, hydrophobic, and hydrogen bond acceptor properties. These results were used to guide the rational design of new nAChR ligands such as 48-52 and 54, which were subsequently synthesized for the first time and tested. Key steps of our synthetic approaches were successfully applied Stille and Suzuki cross-coupling reactions. Predictive r(2) values of 0.614 and 0.660 for CoMFA and CoMSIA, respectively, obtained for 22 in part previously unknown ligands for the (alpha4)(2)(beta2)(3) subtype, demonstrate the high quality of the 3D QSAR models.
• Inversion of the Rectifying Effect in Diblock Molecular Diodes by Protonation
  作者：Gustavo M. Morales、Ping Jiang、Shenwen Yuan、Youngu Lee、Arturo Sanchez、Wei You、Luping Yu

  DOI：10.1021/ja051332c

  日期：2005.8.1

  A new molecular diode based on biphenyl-co-bispyrimidine was synthesized and showed a pronounced rectifying effect. Further studies indicate that protonation on the nitrogen atoms of the diode molecule by strong acids can reversibly alter the rectifying direction. This phenomenon can be envisioned as a starting point for single molecule detection devices.