N-butyl-4-methyl-N-(oct-1-ynyl)benzenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-butyl-4-methyl-N-(oct-1-ynyl)benzenesulfonamide
• 英文别名: N-butyl-4-methyl-N-oct-1-ynylbenzenesulfonamide
• 化学式: C₁₉H₂₉NO₂S
• 分子量: 335.511
• InChiKey: JVKZULRKTWHCQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-butyl-4-methyl-N-(oct-1-ynyl)benzenesulfonamide 在 [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) (2:1) toluene adduct 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到N,N'-(2-hexyl-4-pentylcyclopenta-1,4-diene-1,3-diyl)bis(N-butyl-4-methylbenzenesulfonamide)
  参考文献：
  名称：

  在金催化中利用亚酰胺的双价反应性：炔烃二聚反应的罕见案例

  摘要：

  结果的金矿：在金（I）络合物的存在下，一系列的酰胺被二聚了。这种前所未有的转变涉及关键的酮亚胺中间体的形成，该中间体起反应以形成各种环状和非环状产物。乙酰胺的取代模式决定了形成哪种产物（参见方案； EWG =吸电子基团，Ts =对甲苯磺酰基）。

  DOI：

  10.1002/anie.201100327

文献信息

• Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and <i>Z</i>-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides
  作者：Xuejun Zhang、Yanshi Zhang、Jian Huang、Richard P. Hsung、Kimberly C. M. Kurtz、Jossian Oppenheimer、Matthew E. Petersen、Irina K. Sagamanova、Lichun Shen、Michael R. Tracey

  DOI：10.1021/jo060230h

  日期：2006.5.1

  method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry

  在此描述了用于将各种酰胺与炔基溴化物偶联的通用且有效的方法。这种新颖的酰胺化反应涉及使用五水合硫酸铜（II）和1,10-菲咯啉来指导sp-C-N键形成的催化方案，从而通过分子内酰胺化形成结构上多样的酰胺，包括大环酰胺。鉴于对酰胺化学的浓厚兴趣，这种原子经济的酰胺合成方法应引起有机合成界的进一步关注。
• Synthesis of vinylpyrroles, vinylfurans and vinylindoles via a Brønsted acid catalyzed highly regio- and stereoselective cis-hydroarylation of ynamides
  作者：Yanshi Zhang

  DOI：10.1016/j.tet.2005.11.079

  日期：2006.4

  A highly regio- and stereoselective Brønsted acid-catalyzed coupling of ynamides and aromatic heterocycles, such as pyrroles, furans, and indoles is described. This process is the equivalent of hydroarylation of ynamides, and leads to the efficient syntheses of an array of vinylheterocycles. Diels–Alder reaction between the vinylindoles and DMAD afforded carbazole derivatives in good yields.

  描述了高度区域选择性和立体选择性的布朗斯台德酸催化的酰胺和芳族杂环，例如吡咯，呋喃和吲哚的偶合。该过程等同于乙酰胺的氢化芳基化，并导致一系列乙烯基杂环的有效合成。乙烯基吲哚和DMAD之间的Diels-Alder反应可得到高产率的咔唑衍生物。
• Syntheses of vinylindoles via a Brønsted acid catalyzed highly regio- and stereoselective cis-hydroarylation of ynamides
  作者：Yanshi Zhang

  DOI：10.1016/j.tetlet.2005.07.098

  日期：2005.9

  A highly regio- and stereoselective Bronsted acid-catalyzed coupling of ynamides and indoles is described. This process is the equivalent of hydroarylation of ynamides and leads to the efficient syntheses of vinylindoles. Diels-Alder reaction between the vinylindoles and DMAD afforded carbazole derivatives in good yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Taking Advantage of the Ambivalent Reactivity of Ynamides in Gold Catalysis: A Rare Case of Alkyne Dimerization
  作者：Søren Kramer、Yann Odabachian、Jacob Overgaard、Mario Rottländer、Fabien Gagosz、Troels Skrydstrup

  DOI：10.1002/anie.201100327

  日期：2011.5.23

  A gold mine of results: A series of ynamides have been dimerized in the presence of a gold(I) complex. This unprecedented transformation involves the formation of a key keteniminium intermediate that reacts to form a variety of cyclic and acyclic products. The substitution pattern of the ynamide determines which product is formed (see scheme; EWG=electron‐withdrawing group, Ts=p‐toluenesulfonyl).

  结果的金矿：在金（I）络合物的存在下，一系列的酰胺被二聚了。这种前所未有的转变涉及关键的酮亚胺中间体的形成，该中间体起反应以形成各种环状和非环状产物。乙酰胺的取代模式决定了形成哪种产物（参见方案； EWG =吸电子基团，Ts =对甲苯磺酰基）。