N-octylcyclohexanecarboxamide | 543692-85-9

• 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: N-octylcyclohexanecarboxamide
• CAS: 543692-85-9
• 化学式: C₁₅H₂₉NO
• 分子量: 239.401
• InChiKey: NIWNFEABZJZVCA-UHFFFAOYSA-N

物化性质

• 沸点：
  388.8±9.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-octylcyclohexanecarboxamide 在 sodium 2-methyl-2-adamantoxide 、 dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II) 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 20.0~160.0 ℃ 、8.0 MPa 条件下， 反应 48.0h， 生成 N-octylpivalamide
  参考文献：
  名称：

  Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor

  摘要：

  A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.047
• 作为产物：
  描述：

  N-octylnonanamide 在 sodium 2-methyl-2-adamantoxide 、 dichlorobis(dicyclohexylphosphinomethylpyridine)-ruthenium (II) 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 20.0~160.0 ℃ 、8.0 MPa 条件下， 反应 48.0h， 生成 N-octylcyclohexanecarboxamide
  参考文献：
  名称：

  Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor

  摘要：

  A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.047

文献信息

• Ligand, metal complex containing ligand, and reaction using metal complex containing ligand
  申请人：National University Corporation Nagoya University

  公开号：US09463451B2

  公开（公告）日：2016-10-11

  A hydrogen transfer reaction may be more efficiently promoted by using a metal complex represented by Formula (2): (wherein, R1 to R8 are the same or different, and each represents a hydrogen atom, a substituted or unsubstituted alkyl group or the like; or wherein; R1 and R2, R2 and R3, R3 and R4, R4 and R5, and R5 and R6 are respectively bonded to each other to form a bivalent hydrocarbon group; R9 are the same or different, and each represents an alkyl group or cycloalkyl group; M is ruthenium (Ru) or the like; X is a ligand; and n is 0, 1 or 2). More specifically, the metal complex enables a hydrogenation reaction of various substrates having a stable carbonyl group or the like to be advanced with a high yield under mild conditions.

  一个氢转移反应可能通过使用由式（2）表示的金属配合物更有效地促进： （其中，R1至R8相同或不同，每个代表氢原子，取代或未取代的烷基基团或类似物；或其中；R1和R2，R2和R3，R3和R4，R4和R5，以及R5和R6分别相互连接以形成二价碳氢基团； R9相同或不同，每个代表烷基基团或环烷基基团； M为钌（Ru）或类似物； X为配体；以及 n为0、1或2）。 更具体地说，该金属配合物使具有稳定羰基团或类似物的各种底物的氢化反应在温和条件下高产率地进行。
• An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines
  作者：Andreas P. Häring、Phillip Biallas、Stefan F. Kirsch

  DOI：10.1002/ejoc.201601625

  日期：2017.3.17

  discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous

  我们发现 2,2-二叠氮基乙酰乙酸酯是一类具有基本未知反应性的化合物，可以通过一种不涉及任何试剂的新策略与胺偶联。2,2-二叠氮乙酸酯是碳-碳键断裂下的非常规离去基团。该反应导致酰胺键的构建，耐受各种官能度，并且在实验简单的条件下在多种溶剂中同样表现良好。我们还证明可以避免 2,2-二叠氮基酰基乙酸酯化合物的分离：在室温下在胺存在下用 (Bu4N)N3 和碘处理酰基乙酸酯时很容易碎裂。通过使用这种方法，具有各种结构基序的多种酰基乙酸酯被直接转化为酰胺。
• Copper-Catalyzed Carbonylative Synthesis of Aliphatic Amides from Alkanes and Primary Amines via C_(sp3)–H Bond Activation
  作者：Yahui Li、Fengxiang Zhu、Zechao Wang、Xiao-Feng Wu

  DOI：10.1021/acscatal.6b01413

  日期：2016.8.5

  Amides are important intermediates and building blocks in organic synthesis. Among the known preparation procedures, aminocarbonylation is an interesting and powerful tool. However, most of the studies were focused on noble metal-catalyzed synthesis of aromatic amides. Herein, we describe an attractive copper-catalyzed synthesis of aliphatic amides from alkanes and amines. A variety of amides were

  酰胺是有机合成中的重要中间体和基石。在已知的制备方法中，氨基羰基化是一种有趣且功能强大的工具。然而，大多数研究集中在贵金属催化的芳族酰胺的合成上。在本文中，我们描述了从烷烃和胺中有吸引力的铜催化的脂肪族酰胺的合成。通过用不同的胺对烷烃的C （sp3） -H键进行羰基化，可以制备出高收率的各种酰胺。可以观察到良好的官能团耐受性。
• LIGAND, METAL COMPLEX CONTAINING LIGAND, AND REACTION USING METAL COMPLEX CONTAINING LIGAND
  申请人：NATIONAL UNIVERSITY CORPORATION NAGOYA UNIVERSITY

  公开号：US20160107151A1

  公开（公告）日：2016-04-21

  A hydrogen transfer reaction may be more efficiently promoted by using a metal complex represented by Formula (2): (wherein, R 1 to R 8 are the same or different, and each represents a hydrogen atom, a substituted or unsubstituted alkyl group or the like; or wherein; R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 are respectively bonded to each other to form a bivalent hydrocarbon group; R 9 are the same or different, and each represents an alkyl group or cycloalkyl group; M is ruthenium (Ru) or the like; X is a ligand; and n is 0, 1 or 2). More specifically, the metal complex enables a hydrogenation reaction of various substrates having a stable carbonyl group or the like to be advanced with a high yield under mild conditions.

  一种氢转移反应可以更有效地促进，通过使用由公式（2）表示的金属配合物：（其中，R1至R8相同或不同，每个代表氢原子，取代或未取代的烷基或类似物; 或其中; R1和R2，R2和R3，R3和R4，R4和R5以及R5和R6分别与彼此结合形成双价碳氢基; R9相同或不同，每个代表烷基或环烷基; M是钌（Ru）或类似物; X是配体; n为0，1或2）。更具体地说，该金属配合物使得具有稳定的羰基基团或类似物的各种底物的氢化反应可以在温和的条件下高产率地进行。
• US9463451B2
  申请人：——

  公开号：US9463451B2

  公开（公告）日：2016-10-11