(E)-3-(cyclohex-1-en-1-yl)acrylamide | 22031-65-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-3-(cyclohex-1-en-1-yl)acrylamide
• 英文别名: trans-3--acrylsaeureamid；(E)-3-(cyclohexen-1-yl)prop-2-enamide
• CAS: 22031-65-8
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: IRVHZHRANWHIFR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(cyclohex-1-en-1-yl)acrylamide 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 (E)-2-Hydroxyimino-3-[(E)-2-nitrocyclohexylidene]propanamide
  参考文献：
  名称：

  New reagents for controlled release of nitric oxide. Structure-stability relationships

  摘要：

  The synthesis and structure-stability relationships of a series of novel FK409 derivatives (1, 2, and 3) are described. The rates of decomposition in aqueous solution (pH 8.0, 30 degrees C) were parallel with those of spontaneous NO release measured by ESR spectroscopy using carboxy-PTIO. The compounds can cover a wide range of NO releasing rates by appropriate modification of the molecule.

  DOI：

  10.1016/0960-894x(95)00547-7
• 作为产物：
  描述：

  (2-氨基-2-氧代乙基)磷酸二乙酯 、 1-cyclohexene-1-carboxaldehyde 在 potassium tert-butylate 作用下， 生成 (E)-3-(cyclohex-1-en-1-yl)acrylamide
  参考文献：
  名称：

  New reagents for controlled release of nitric oxide. Structure-stability relationships

  摘要：

  The synthesis and structure-stability relationships of a series of novel FK409 derivatives (1, 2, and 3) are described. The rates of decomposition in aqueous solution (pH 8.0, 30 degrees C) were parallel with those of spontaneous NO release measured by ESR spectroscopy using carboxy-PTIO. The compounds can cover a wide range of NO releasing rates by appropriate modification of the molecule.

  DOI：

  10.1016/0960-894x(95)00547-7

文献信息

• Iron-catalyzed hydroaminocarbonylation of alkynes: Selective and efficient synthesis of primary α,β-unsaturated amides
  作者：Zijun Huang、Jia Tang、Xiongwei Jiang、Tianle Xie、Minmin Zhang、Donghui Lan、Shaofeng Pi、Zhengde Tan、Bing Yi、Yuehui Li

  DOI：10.1016/j.cclet.2022.01.080

  日期：2022.11

  α,β-Unsaturated primary amides are important intermediates and building blocks in organic synthesis. Herein, we report a ligand-free iron-catalyzed hydroaminocarbonylation of alkynes using NH4HCO3 as the ammonia source, enabling the highly efficient and regioselective synthesis of linear α,β-unsaturated primary amides. Various aromatic and aliphatic alkynes are transformed into the desired linear α

  α,β-不饱和伯酰胺是有机合成中重要的中间体和结构单元。在此，我们报道了一种使用 NH 4 HCO 3作为氨源的无配体铁催化炔烃的氢化氨基羰基化反应，从而能够高效和区域选择性地合成线性α,β-不饱和伯酰胺。各种芳香族和脂肪族炔烃以良好至极好的收率转化为所需的线性α,β-不饱和伯酰胺。进一步的研究表明，使用 NH 4 HCO 3作为氨源是获得良好收率和选择性的关键。该路线的实用性通过线性α，β的合成得到证明-不饱和酰胺，包括类香草素受体 1 拮抗剂 TRPV-1。