isonicotinic acid octyl ester

• 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: isonicotinic acid octyl ester
• 英文别名: octyl 4-pyridinecarboxylate；n-octyl isonicotinate；octyl isonicotinate；Isonicotinic acid, octyl ester；octyl pyridine-4-carboxylate
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: GGLVNUJXRYCZHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛醇 、 氯化异氰盐酸盐 在 吡啶 作用下， 反应 16.0h， 以92%的产率得到isonicotinic acid octyl ester
  参考文献：
  名称：

  Synthesis and evaluation of antibacterial activity of (R)-2-methylheptyl isonicotinate, a putative naturally occurring bioactive agent

  摘要：

  A putative antibacterial and antifungal compound, (R)-2-methylheptyl isonicotinate, was synthesized via reductive lactone alkylation of (R)-4-methyldihydrofuran-2(3H)-one. Structural characterisation data as well as bioassay results (with Bacillus subtilis or Escherichia coli) contradict those previously reported. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.10.045

文献信息

• CeO2-catalysed one-pot selective synthesis of esters from nitriles and alcohols
  作者：Masazumi Tamura、Takuya Tonomura、Ken-ichi Shimizu、Atsushi Satsuma

  DOI：10.1039/c2gc16424h

  日期：——

  were tested for one-pot selective synthesis of esters from nitriles and alcohols. Ceria (CeO2) showed more than two orders of magnitude higher activity than the other oxides. CeO2 acted as a reusable and effective catalyst for the ester synthesis from various nitriles and alcohols under neutral and solvent-free conditions at 160 °C. This method provides a rare example for the synthesis of heteroaromatic

  十三种金属 氧化物 被测试用于一锅的选择性合成 酯类 从 腈 和 酒类。二氧化铈（CeO 2）的活性比另一个高出两个数量级氧化物。CeO 2起到可重复使用和有效的作用催化剂 为了 酯 综合各种 腈 和 酒类 在中立和 溶剂160°C的无温度条件。该方法为杂芳族化合物的合成提供了一个罕见的例子酯类通过传统的催化酯化方法难以合成。有价值的酯类诸如吡啶甲酸烷基酯和烟酸苄基酯之类的化合物被合成，证明了本方法的实用方面。动力学研究提出以下反应机理：（1）高氧2和ROH在CeO 2上解离，（2）羟基（OH δ−）对吸附的亲核攻击。腈在CeO 2上，导致形成伯酰胺，（3）醇盐物种（OR δ−）亲核攻击酰胺 作为限速步骤。
• Barry, Jean; Bram, Georges; Petit, Alain, Heterocycles, 1985, vol. 23, # 4, p. 875 - 880
  作者：Barry, Jean、Bram, Georges、Petit, Alain

  DOI：——

  日期：——
• Mucor miehei lipase catalyzed transesterifications on aromatic and heteroaromatic substrates. A general survey
  作者：María Gema Martín-Muñoz、Marta Fierros、María Isabel Rodriguez-Franco、Santiago Conde

  DOI：10.1016/s0040-4020(01)81352-1

  日期：——

  An investigation on Mucor miehei lipase-catalyzed transesterifications of 16 aromatic and heteroaromatic esters in organic solvents is described. The points studied were the activity and regioselectivity of the enzyme-catalyzed reaction of either one or two ester groups situated in different positions on several heterocyclic systems with an aliphatic alcohol. The reactions took place in moderate to good yields and, in some cases, regioselectively.
• BARRY, J.;BRAM, G.;PETIT, A., HETEROCYCLES, 1985, 23, N 4, 875-880
  作者：BARRY, J.、BRAM, G.、PETIT, A.

  DOI：——

  日期：——
• Synthesis and evaluation of antibacterial activity of (R)-2-methylheptyl isonicotinate, a putative naturally occurring bioactive agent
  作者：Jia Cao、Ben Adler、Patrick Perlmutter

  DOI：10.1016/j.bmcl.2015.10.045

  日期：2015.11

  A putative antibacterial and antifungal compound, (R)-2-methylheptyl isonicotinate, was synthesized via reductive lactone alkylation of (R)-4-methyldihydrofuran-2(3H)-one. Structural characterisation data as well as bioassay results (with Bacillus subtilis or Escherichia coli) contradict those previously reported. (C) 2015 Elsevier Ltd. All rights reserved.