4-methyl-N-(oct-2-yn-1-yl)benzenesulfonamide | 1333226-40-6

• 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: 4-methyl-N-(oct-2-yn-1-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-oct-2-ynylbenzenesulfonamide
• CAS: 1333226-40-6
• 化学式: C₁₅H₂₁NO₂S
• 分子量: 279.403
• InChiKey: PKFPTAVJUIXGLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(oct-2-yn-1-yl)benzenesulfonamide 在 二甲基苯基硅烷 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以81%的产率得到(Z)-4-methyl-N-(oct-2-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Nanoporous Gold Catalyst for Highly Selective Semihydrogenation of Alkynes: Remarkable Effect of Amine Additives

  摘要：

  We report for the first time the highly selective semihydrogenation of alkynes using the unsupported nanoporous gold (AuNPore) as a catalyst and organosilanes with water as a hydrogen source. Under the optimized reaction conditions, the present semihydrogenation of various terminal- and internal-alkynes affords the corresponding alkenes in high chemical yields and excellent Z-selectivity without any, over-reduced alkanes. The use of DMF as solvent, which generates amines in situ, or pyridine as an additive is crucial to suppress the association of hydrogen atoms on AuNPore to form H-2 gas, which is unable to reduce alkynes on the unsupported gold catalysts. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity. In addition, the SEM and TEM characterization of nanoporosity show that the AuNPore catalyst has a bicontinuous 3D structure and a high density of atomic steps and kinks on ligament surfaces, which should be one of the important origins of catalytic activity.

  DOI：

  10.1021/ja3087592
• 作为产物：
  描述：

  2-辛炔-1-醇 在 四溴化碳 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.34h， 生成 4-methyl-N-(oct-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Nanoporous Gold Catalyst for Highly Selective Semihydrogenation of Alkynes: Remarkable Effect of Amine Additives

  摘要：

  We report for the first time the highly selective semihydrogenation of alkynes using the unsupported nanoporous gold (AuNPore) as a catalyst and organosilanes with water as a hydrogen source. Under the optimized reaction conditions, the present semihydrogenation of various terminal- and internal-alkynes affords the corresponding alkenes in high chemical yields and excellent Z-selectivity without any, over-reduced alkanes. The use of DMF as solvent, which generates amines in situ, or pyridine as an additive is crucial to suppress the association of hydrogen atoms on AuNPore to form H-2 gas, which is unable to reduce alkynes on the unsupported gold catalysts. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity. In addition, the SEM and TEM characterization of nanoporosity show that the AuNPore catalyst has a bicontinuous 3D structure and a high density of atomic steps and kinks on ligament surfaces, which should be one of the important origins of catalytic activity.

  DOI：

  10.1021/ja3087592

文献信息

• Copper(I)-Catalyzed Regio- and Stereoselective Intramolecular Alkylboration of Propargyl Ethers and Amines
  作者：Hiroaki Iwamoto、Yu Ozawa、Koji Kubota、Hajime Ito

  DOI：10.1021/acs.joc.7b02071

  日期：2017.10.6

  transformed into multisubstituted alkenes through stereospecific transformations. Mechanistic studies showed that the chemo- and stereoselectivity of copper(I)-catalyzed borylation depends on the type of leaving group. Density functional theory calculations suggested that the regioselectivity of the borylcupration of the alkyne is controlled by the electronic effect of the oxygen atom of the propargyl ether

  已经开发了铜（I）催化带有烷基亲电部分的炔丙基醚和胺的区域和立体选择性分子内烷基化。该反应显示出高的官能团耐受性并得到带有杂环的高度官能化的烯基硼酸酯，其在有机化学中是通用的合成中间体。硼酸酯化产物可以通过立体有择的转化而转化为多取代的烯烃。机理研究表明，铜（I）催化的硼酸酯化反应的化学和立体选择性取决于离去基团的类型。
• Cross-Coupling of Grignard Reagents with Sulfonyl-Activated sp3 Carbon-Nitrogen Bonds
  作者：Man-Bo Li、Xiang-Ling Tang、Shi-Kai Tian

  DOI：10.1002/adsc.201100285

  日期：2011.8

  Sulfonyl-activated sp3 carbon-nitrogen bonds have been found to be cleaved by Grignard reagents in the presence of 5 mol% of copper(I) iodide (CuI). Significantly, a broad range of sulfonyl-activated benzylic, allylic, and propargylic amines smoothly undergo the cross-coupling reaction with Grignard reagents to afford structurally diverse coupling products in good to excellent yields and with high

  已经发现，在5mol％的碘化亚铜（I）存在下，格氏试剂可将磺酰基活化的sp 3碳-氮键裂解。重要的是，广泛的磺酰基活化的苄基，烯丙基和炔丙基胺与格利雅试剂进行平滑的交叉偶联反应，从而提供结构多样的偶联产物，收率高至优异，并具有较高的化学，区域和立体选择性。此外，已经证明S N 2机理参与交叉偶联反应，该交叉偶联反应允许由旋光的α-支化胺衍生物不对称地合成手性烃。
• Gold(I)‐Catalyzed and PTSA‐Promoted Cycloisomerization of Ynamides to Access Pyrrole Substituted α,β‐Unsaturated Ketones**
  作者：Shivani Choudhary、Gayyur、Nayan Ghosh

  DOI：10.1002/ejoc.202201223

  日期：2023.1.24

  In this work, a new ynamide scaffold has been designed, synthesized and later applied in a gold-catalyzed cycloisomerization reaction to access pyrrole containing α,β-unsaturated ketones in low-to-moderate yields. Interestingly, the trans product has been obtained as a major isomer.

  在这项工作中，设计、合成了一种新的 ynamide 支架，随后将其应用于金催化的环化异构化反应，以低至中等收率获得含有 α,β-不饱和酮的吡咯。有趣的是，反式产物已作为主要异构体获得。