1,4-bis(trimethylsilyl)-1,4-dihydropyridine | 29173-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,4-bis(trimethylsilyl)-1,4-dihydropyridine
• 英文别名: trimethyl-(1-trimethylsilyl-4H-pyridin-4-yl)silane
• CAS: 29173-25-9
• 化学式: C₁₁H₂₃NSi₂
• 分子量: 225.481
• InChiKey: MJLQTXJEKQTNRI-UHFFFAOYSA-N

物化性质

• 沸点：
  45-50 °C(Press: 33 Torr)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-bis(trimethylsilyl)-1,4-dihydropyridine 在 air 作用下， 生成 4-(三甲基甲硅烷基)吡啶
  参考文献：
  名称：

  1,4-双(三甲基甲硅烷基)-1,4-二氢吡啶与羰基化合物的反应：一种区域选择性合成3-烷基吡啶的新方法

  摘要：

  描述了在吡啶的 3-位引入烷基的新方法：吡啶的还原二甲硅烷基化，其 2-甲基、3-甲基和 4-甲基衍生物提供相应的 1,4-二甲硅烷基-1,4-二氢吡啶类。在催化量的四丁基氟化铵存在下，这些二氢吡啶与各种醛和酮顺利反应生成 3-烷基吡啶。

  DOI：

  10.1246/bcsj.60.1497
• 作为产物：
  描述：

  吡啶 、 三甲基氯硅烷 生成 1,4-bis(trimethylsilyl)-1,4-dihydropyridine
  参考文献：
  名称：

  TSUGE, OTOHIKO;KANEMASA, SHUJI;NARITOMI, TOSHIO;TANAKA, JUNJI, CHEM. LETT., 1984, N 7, 1255-1258

  摘要：

  DOI：

文献信息

• Characterization of covalent Ene adduct intermediates in “hydride equivalent” transfers in a dihydropyridine model for NADH reduction reactions
  作者：R. Daniel Libby、Ryan A. Mehl

  DOI：10.1016/j.bioorg.2011.10.002

  日期：2012.2

  compounds has produced the first direct evidence for an obligatory covalent adduct between a dihydropyridine and substrate in a reduction reaction. The reactions were monitored by NMR spectroscopy. In all reactions studied, the covalent adduct was the first new species detected and its decomposition to form products could be observed. Concentrations of adducts were sufficiently high at steady-state

  对NADH模型1,4-二（三甲基甲硅烷基）-1,4-二氢吡啶7与一系列α，β-不饱和氰基和羰基化合物的反应的研究为强制性共价提供了第一个直接证据在还原反应中二氢吡啶与底物之间的加合物。通过NMR光谱监测反应。在所有研究的反应中，共价加合物是第一个检测到的新物种，并且可以观察到其分解生成产物。加合物的浓度在稳态下足够高，可以直接从反应混合物的NMR光谱中确定其结构。加合物结构是由7与底物之间的Ene反应所预期的那些。该第一反应步骤导致C 4的转移氢原子与底物7形成氢原子，并在二氢吡啶环的C 2与底物α原子之间形成共价键。这些烯加合物中间体的发现完善了在NADH模型反应中观察到的机制范围，从而涵盖了具有自由基中间体，没有可检测的中间体和现在的共价中间体的那些机理。将形成Ene加合物的过渡态的几何形状与理论过渡态模型的几何形状和酶-底物/抑制剂复合物的晶体结构进行比较，以表明二氢吡啶环和底物处于
• Substituted 1,2-dihydropyridines and process for preparing same
  申请人：Monsanto Company

  公开号：US04013661A1

  公开（公告）日：1977-03-22

  Substituted 1,2-dihydropyridines of the formula ##SPC1## In which R and R.sup.2 are selected from the group consisting of hydrogen, --NH.sub.2, silyl, silyl linked via oxygen, silyl linked via nitrogen, sulfamyl, organosulfonamido, nitro, organic radical, organic radical linked via oxygen, organic radical linked via sulfur, organic radical linked via nitrogen, organic radical linked via --SO-- and organic radical linked via --SO.sub.2 --; with the proviso that the R.sup.2 groupings when joined together form an ortho condensed cyclic or polycyclic hydrocarbon; R.sup.1 is a member selected from the group consisting of hydrogen, --NH.sub.2, silyl, silyl linked via oxygen, silyl linked via nitrogen, sulfamyl, organosulfonamido, nitro, organic radical, organic radical linked via oxygen, organic radical linked via sulfur, organic radical linked via nitrogen, organic radical linked via --SO-- organic radical linked via --SO.sub.2 --, mercapto, sulfino and sulfo; R.sup.3 is a member selected from the group consisting of hydrogen, halogen, and methyl; and Z is a member selected from the group consisting of halogen and an electron-withdrawing group containing an electronegative atom doubly or triply bonded to a more positive atom which atom is singly bonded to the carbon atom attached to the pyridine ring. Exemplary of such compositions is 1,4-bis(trimethylsilyl)-2-(1-cyanoethyl)-1,2-dihydropyridine. The compounds of the invention are useful as antioxidants for polyphenyl ethers, as stabilizers for halogenated polyhydrocarbons, as curing agents for silicones and epoxide resins, as dyeing improvers for polyesters and as fuel additives for imparting hypergolic properties.

  将公式中的1,2-二氢吡啶置换为##SPC1##，其中R和R.sup.2选自氢、--NH.sub.2、硅烷基、通过氧原子连接的硅烷基、通过氮原子连接的硅烷基、磺酰胺基、有机磺酰胺基、硝基、有机基、通过氧原子连接的有机基、通过硫原子连接的有机基、通过氮原子连接的有机基、通过--SO--连接的有机基和通过--SO.sub.2--连接的有机基等组成的群；R.sup.1选自氢、--NH.sub.2、硅烷基、通过氧原子连接的硅烷基、通过氮原子连接的硅烷基、磺酰胺基、有机磺酰胺基、硝基、有机基、通过氧原子连接的有机基、通过硫原子连接的有机基、通过氮原子连接的有机基、通过--SO--连接的有机基、通过--SO.sub.2--连接的有机基、巯基、磺基和亚磺基；R.sup.3选自氢、卤素和甲基；Z选自卤素和含有与更正电原子双键或三键连接的带有电子亲和原子的取代基，该原子与连接到吡啶环上的碳原子形成单键。这种化合物的示例是1,4-双(三甲基硅基)-2-(1-氰乙基)-1,2-二氢吡啶。该发明的化合物可用作多酚醚的抗氧化剂，卤代聚烃的稳定剂，硅烷和环氧树脂的固化剂，改善涤纶的染料助剂以及用于赋予超燃特性的燃料添加剂。
• RECIOSELECTIVE ALKYL GROUP INTRODUCTION AT THE 3-POSITION OF PYRIDINE VIA 1,4-BIS(TRIMETHYLSILYL)-1,4-DIHYDROPYRIDINE
  作者：Otohiko Tsuge、Shuji Kanemasa、Toshio Naritomi、Junji Tanaka

  DOI：10.1246/cl.1984.1255

  日期：1984.7.5

  The reaction of 1,4-bis(trimethylsilyl)-1,4-dihydropyridine with aldehydes and ketones in the presence of tetrabutylammonium fluoride offers a convenient method for the preparation of 3-alkylpyridines.

  在四丁基氟化铵存在下，1,4-双（三甲基甲硅烷基）-1,4-二氢吡啶与醛和酮的反应为制备 3-烷基吡啶提供了一种方便的方法。
• [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors
  作者：Gregory R. Martinez、Donald R. Hirschfeld、Patrick J. Maloney、Diana S. Yang、Roberto P. Rosenkranz、K. A. M. Walker

  DOI：10.1021/jm00124a027

  日期：1989.4

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.
• TSUGE OTOHIKO; KANEMASA SHUJI; NARITOMI TOSHIO; TANAKA JUNJI, BULL. CHEM. SOC. JAP., 60,(1987) N 4, 1497-1504
  作者：TSUGE OTOHIKO、 KANEMASA SHUJI、 NARITOMI TOSHIO、 TANAKA JUNJI

  DOI：——

  日期：——