N-butylisonicotinamide | 10354-58-2

• 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: N-butylisonicotinamide
• 英文别名: N-(n-butyl)isonicotinamide；N-butylpyridine-4-carboxamide
• CAS: 10354-58-2
• 化学式: C₁₀H₁₄N₂O
• mdl: MFCD00462322
• 分子量: 178.234
• InChiKey: IDNGPRYAMMACEI-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  155-156 °C(Press: 1 Torr)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-butylisonicotinamide 在 platinum(IV) oxide 氢气 、 三乙胺 作用下， 以 溶剂黄146 、 正丁醇 为溶剂， 30.0 ℃ 、344.73 kPa 条件下， 反应 24.0h， 生成 4-amino-6,7-dimethoxy-2-<4-(N-butylcarbamoyl)piperidino>quinazoline
  参考文献：
  名称：

  2,4-Diamino-6,7-dimethoxyquinazolines. 2. 2-(4-Carbamoylpiperidino) derivatives as .alpha.1-adrenoceptor antagonists and antihypertensive agents

  摘要：

  A series of 4-amino-2-(4-carbamoylpiperidino)-6,7-dimethoxyquinazolines (2) were synthesized and evaluated for alpha-adrenoceptor affinity and antihypertensive activity. These compounds displayed high binding affinity (Ki, 10(-9)-10(-10) M) and selectivity for alpha 1-adrenoceptors in vitro, and 12, 14, 21-26, and 29 showed similar potency to prazosin. Compounds 26 and 28 were also shown to be competitive antagonists of the postjunctional, vasoconstrictor action of norepinephrine with no significant activity at prejunctional alpha 2-sites. The high binding affinity for series 2 is rationalized in terms of enhanced basicity of the quinazoline nucleus (pKa's: 12, 7.38; 26, 7.53; prazosin, 6.8) and hydrophobic interactions of the carbamoyl substituents. Molecular mechanics calculations and computer-assisted superimposition suggest that the quinazoline 2-substituents in prazosin and 2 occupy the alpha 1-adrenoceptor site in different manners. Antihypertensive activity was evaluated after oral administration (5 mg/kg) to spontaneously hypertensive rats, and 11, 15, 21, 22, and 26 displayed sustained prazosin-like efficacy at the 6-h time point. The high alpha 1-adrenoceptor affinity demonstrated by series 2 in vitro suggests that these marked, and prolonged, falls in blood pressure result from selective blockade of the alpha 1-mediated vasoconstrictor effects of norepinephrine.

  DOI：

  10.1021/jm00389a007
• 作为产物：
  描述：

  异烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 N-butylisonicotinamide
  参考文献：
  名称：

  多巴胺聚合物的电化学行为。多巴胺释放作为突触的原始类似物

  摘要：

  Liberation et detection de la dopamine, emploi de cette electrodepolymere comme catalyseur de l'oxydation du NADH en solution

  DOI：

  10.1021/ja00354a016

文献信息

• A highly efficient Pd–C catalytic hydrogenation of pyridine nucleus under mild conditions
  作者：Chuanjie Cheng、Jimin Xu、Rui Zhu、Lixin Xing、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tet.2009.08.011

  日期：2009.10

  A synergistic Pd–C catalytic hydrogenation of 4-pyridinecarboxamides straightforward to 4-piperidinecarboxamide hydrochlorides was developed in the presence of ClCH2CHCl2. It provided a novel strategy for highly efficient hydrogenation of pyridine nuclear by using low-cost Pd–C catalyst under mild conditions.

  在存在ClCH 2 CHCl 2的情况下，开发了对4-吡啶羧甲酰胺盐酸盐直接作用的4-吡啶甲酰胺的Pd-C协同催化氢化反应。它通过在温和条件下使用低成本的Pd-C催化剂，为吡啶核的高效加氢提供了一种新的策略。
• CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in water <i>via</i> benzylic sp³ C–H activation
  作者：Marzieh Rousta、Dariush Khalili、Ali Khalafi-Nezhad、Edris Ebrahimi

  DOI：10.1039/d1nj03982b

  日期：——

  activity of the rGO/Fe3O4–CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals using tert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation

  通过简便的化学方法制备了磁铁矿还原的氧化石墨烯负载的 CuO 纳米复合材料 ( rGO /Fe 3 O 4 –CuO)，并通过傅里叶变换红外光谱 (FTIR)、X 射线衍射 (XRD)、UV-vis光谱、扫描电子显微镜 (SEM)、透射电子显微镜 (TEM)、能量色散光谱 (EDS)、Brunauer-Emmett-Teller (BET) 分析、振动样品磁强计 (VSM) 和热重 (TG) 分析。rGO/Fe 3 O 4的催化活性-CuO纳米复合材料在甲基芳烃与游离胺的直接氧化酰胺化反应中被探测到。使用叔丁基过氧化氢 (TBHP) 作为“绿色”氧化剂和在水中的低毒性 TBAI，在室温下从廉价的原料化学品中有效地制备了各种芳香族和脂肪族酰胺。该方法将甲基芳烃的氧化和酰胺键的形成结合到一个操作中。此外，合成的纳米复合材料可以使用外部磁铁从反应混合物中分离出来，并在连续六次运行中重复使用，催化活性没有明显降低。
• Reusable Manganese Catalyst for Site‐Selective Pyridine C−H Arylations and Alkylations
  作者：Isaac Choi、Zhigao Shen、Emanuel Ronge、Volker Karius、Christian Jooss、Lutz Ackermann

  DOI：10.1002/chem.202101894

  日期：2021.9.6

  Herein, we disclose a recyclable, hybrid manganese catalyst for site-selective azine C−H activation by weak amide assistance. The novel, reusable catalyst enabled C3–H arylation and C3–H alkylation with ample scope, and was characterized by detailed transmission electron microscopy analysis.

  在此，我们公开了一种可回收的杂化锰催化剂，用于通过弱酰胺辅助进行位点选择性吖嗪 CH 活化。这种新型、可重复使用的催化剂使 C3-H 芳基化和 C3-H 烷基化具有足够的范围，并通过详细的透射电子显微镜分析进行表征。
• Manganaelectro-Catalyzed Azine C–H Arylations and C–H Alkylations by Assistance of Weakly Coordinating Amides
  作者：Leonardo Massignan、Cuiju Zhu、Xiaoyan Hou、João C. A. Oliveira、Aude Salamé、Lutz Ackermann

  DOI：10.1021/acscatal.1c02516

  日期：2021.9.17

  Oxidative C–H functionalization has faced considerable limitations by the need for stoichiometric amounts of chemical oxidants. In sharp contrast, we herein present the merger of electrosynthesis with non-toxic manganese catalysis for oxidative C–H arylations and C–H alkylations with electricity as the terminal oxidant. Mechanistic experimental studies as well as cyclic voltammetry and scanning electron

  由于需要化学计量的化学氧化剂，氧化 C-H 功能化面临着相当大的限制。与此形成鲜明对比的是，我们在此展示了电合成与无毒锰催化的结合，用于氧化性 C-H 芳基化和以电为终端氧化剂的 C-H 烷基化。机械实验研究以及循环伏安法和扫描电子显微镜分析表明初始快速 C-H 活化。计算研究强调了锰电催化的 C-H 芳基化在使用单齿苯甲酰胺时的独特特征，而铁电催化仍然仅限于强配位的N，N-双齿导向基团。
• Manganese(II/III/I)-Catalyzed C–H Arylations in Continuous Flow
  作者：Cuiju Zhu、João C. A. Oliveira、Zhigao Shen、Huawen Huang、Lutz Ackermann

  DOI：10.1021/acscatal.8b00166

  日期：2018.5.4

  Versatile manganese-catalyzed C–H arylations on synthetically meaningful pyridines were accomplished with sustainable MnCl2 as the catalyst. The oxidative C–H functionalizations proved viable with a user-friendly and safe continuous flow setup by weak amide-assisted C–H cleavage via a facile C–H activation regime.

  以可持续的MnCl 2为催化剂，在锰合成的有意义的吡啶上进行了多功能的锰催化的C–H芳基化反应。通过简便的C–H活化机制，通过弱酰胺辅助的C–H裂解，氧化C–H官能化在用户友好和安全的连续流设置中被证明是可行的。