N-烯丙基异烟酰胺 | 244284-09-1

• 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
• 中文名称: N-烯丙基异烟酰胺
• 英文名称: N-allylisonicotinamide
• 英文别名: isonicotinic acid allylamide；Isonicotinsaeure-allylamid；N-prop-2-enylpyridine-4-carboxamide
• CAS: 244284-09-1
• 化学式: C₉H₁₀N₂O
• mdl: MFCD00462320
• 分子量: 162.191
• InChiKey: IMCCMRAPZAYTMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 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-烯丙基异烟酰胺 在 碘代三甲硅烷 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到5-(iodomethyl)-2-(pyridin-4-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  Modular Preparation of 5-Halomethyl-2-oxazolines via PhI(OAc)₂-Promoted Intramolecular Halooxygenation of N-Allylcarboxamides

  摘要：

  A new method for the construction of oxazoline moiety was detailed. Using (diacetoxyiodo)benzene (PIDA) as the reaction promoter and halotrimethylsilane as the halogen source, intramolecular halooxygenation and halothionation of N-allylcarboxamides/N-allylcarbothioamides proceeded readily, leading : to the corresponding 5-halomethyloxazolines/5-halomethylthiazolines in good to excellent isolated yields. The 5-halomethyl products could be converted to different derivatives via conventional nucleophilic substitution methods. The reactions were carried out using easily available starting materials, and did not need harsh reaction conditions. All these features made this reaction a viable method for the construction of different oxazoline and thiazoline structures.

  DOI：

  10.1021/acs.joc.5b01832
• 作为产物：
  描述：

  异烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 N-烯丙基异烟酰胺
  参考文献：
  名称：

  Structure and antiinflammatory activity of isonicotinic and nicotinic amides

  摘要：

  DOI：

  10.1007/bf02464277

文献信息

• Synthesis of Quinolines via Rh(III)-Catalyzed Oxidative Annulation of Pyridines
  作者：Guoyong Song、Xue Gong、Xingwei Li

  DOI：10.1021/jo201266u

  日期：2011.9.16

  Selective synthesis of quinolines has been achieved via oxidative annulation of functionalized pyridines with two alkyne molecules under Rh(III)-catalyzed cascade C–H activation of pyridines using Cu(OAc)2 as an oxidant. The selectivity of this reaction is oxidant-dependent, particularly on the anion of the oxidant.

  喹啉的选择性合成是通过在Rh（III）催化的吡啶级联C–H吡啶活化反应中，使用Cu（OAc）2作为氧化剂，通过官能化的吡啶与两个炔烃分子的氧化环化而实现的。该反应的选择性取决于氧化剂，特别是取决于氧化剂的阴离子。
• Rhodium(iii)-catalyzed oxidative mono- and di-olefination of isonicotinamides
  作者：Xiaohong Wei、Feng Wang、Guoyong Song、Zhengyin Du、Xingwei Li

  DOI：10.1039/c2ob25773d

  日期：——

  [RhCp*Cl2]2 can catalyze the oxidative coupling of secondary isonicotinamides with activated olefins using Cu(OAc)2 as an oxidant. The selectivity can be controlled by the solvent. In MeCN, the mono-olefination and two-fold oxidation reaction is the major pathway, while in THF this reaction gave mostly diolefination products. In both cases, the coupled products contain an exocyclic CC bond.

  [RhCp*Cl2]2能催化次异烟酰胺与活泼烯烃的氧化偶联反应，以Cu(OAc)2作为氧化剂。通过溶剂可以选择性地控制反应。在乙腈中，单烯化与双氧化反应是主要途径，而在四氢呋喃中该反应主要得到二烯化产物。两种情况下，偶联产物都含有一个环外碳碳键。
• Electrochemical oxidative cyclization of olefinic carbonyls with diselenides
  作者：Zhipeng Guan、Yunkun Wang、Huamin Wang、Yange Huang、Siyuan Wang、Hongding Tang、Heng Zhang、Aiwen Lei

  DOI：10.1039/c9gc02665g

  日期：——

  The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C–Se and C–O bonds simultaneously. A series of seleno dihydrofurans and seleno oxazolines, bearing fragile heterocycles, subtle C–I bonds and supernumerary vinyl groups, were

  已经成功地开发了通过电化学氧化促进具有容易获得的二硒化物的烯烃羰基的串联环化反应，这为同时构建C-Se和C-O键提供了一种环境友好的方法。使用这种优雅的螯合策略，可以伪造一系列带有易碎杂环，微妙的C–I键和大量乙烯基的硒代二氢呋喃和硒代恶唑啉。既不需要金属催化剂也不需要外部化学氧化剂来促进这种转变。
• Copper‐Catalyzed Oxidative C−H Bond Functionalization of N‐Allylbenzamide for Regioselective C−N and C−O Bond Formation
  作者：Jala Ranjith、Palakodety Radha Krishna

  DOI：10.1002/asia.201900192

  日期：2019.5.2

  Copper‐catalyzed oxidative couplings of N‐allylbenzamides for C−N and C−O bond formations have been developed through C−H bond functionalization. To demonstrate the utility of this approach, it was applied to the synthesis of β‐aminoimides and imides. To the best of our knowledge, these are the first examples in which different classes of N‐containing compounds have been directly prepared from the

  N-烯丙基苯甲酰胺通过铜催化的C-N和C-O键形成的氧化偶联作用是通过C-H键功能化而开发的。为了证明该方法的实用性，将其应用于β-氨基酰亚胺和酰亚胺的合成。就我们所知，这是第一个实例，其中使用廉价的催化剂/氧化剂/碱（CuSO 4 / TBHP / Cs 2 CO 3） 系统。
• Mercurial Diuretics. I. Addition of Mercuric Chloride and Secondary Amines to Allylamides¹
  作者：Gerhard Wendt、B. Vithal Shetty、William F. Bruce

  DOI：10.1021/ja01525a029

  日期：1959.8