N-[4-(4-chlorophenyl)-4-hydroxybut-2-ynyl]-4-methyl-N-(3-methylbut-2-enyl)benzenesulfonamide | 1174503-08-2

• 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-[4-(4-chlorophenyl)-4-hydroxybut-2-ynyl]-4-methyl-N-(3-methylbut-2-enyl)benzenesulfonamide
• CAS: 1174503-08-2
• 化学式: C₂₂H₂₄ClNO₃S
• 分子量: 417.956
• InChiKey: OFWDXULUSCXECW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[4-(4-chlorophenyl)-4-hydroxybut-2-ynyl]-4-methyl-N-(3-methylbut-2-enyl)benzenesulfonamide 在 吡啶 、 叔丁基过氧化氢 、 三(2-呋喃基)膦 、 三乙胺 、 palladium(II) iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Palladium-Catalyzed Divergent Reactions of 1,6-Enyne Carbonates: Synthesis of Vinylidenepyridines and Vinylidenepyrrolidines

  摘要：

  A method for preparing five- or six-membered heterocyclic compounds from enyne carbonates via palladium catalysis was developed. Enyne carbonates were transformed into 3-vinylidene-1-tosylpyridines 2 in the presence of PdI2 as the catalyst. Using Pd(dba)(2) as the catalyst, 3-vinylidene-1-tosylpyrrolidines 3 were obtained. Further functionalizations of compounds 3 were carried out in a one-pot manner.

  DOI：

  10.1021/jo202590w
• 作为产物：
  描述：

  4-氯苯甲醛 、 N-prenyl-N-propargyltosylamide 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以100%的产率得到N-[4-(4-chlorophenyl)-4-hydroxybut-2-ynyl]-4-methyl-N-(3-methylbut-2-enyl)benzenesulfonamide
  参考文献：
  名称：

  钯催化的1,6-烯炔乙酸酯的环异构化反应形成五元氮化杂环共轭三烯

  摘要：

  已经开发了钯催化的1，6-烯炔乙酸酯的环异构化反应。该环化反应显示出优异的区域选择性和良好的官能团耐受性，以中等至优异的产率获得了五元氮化杂环共轭三烯。所得的共轭三烯可通过狄尔斯-阿尔德反应容易地转化为高度取代的苯。

  DOI：

  10.1016/j.tetlet.2017.11.018

文献信息

• Brønsted Acid Catalyzed Cyclization of Hydroxylated Enynes: A Concise Synthesis of Five-Membered Heterocycles
  作者：Ke-Gong Ji、Jin Chen、Hai-Tao Zhu、Fang Yang、Ali Shaukat、Yong-Min Liang

  DOI：10.1002/chem.201002222

  日期：2011.1.3

  heterocyclic compounds from hydroxylated enynes has been developed. In this reaction, hydroxylated enynes were selectively transformed into five‐membered heterocyclic compounds 2, with an allene moiety at the 3‐position, in the presence of F3CSO3H (0.1 mol %). When R1, R2=Ph, diphenylvinyl‐2,3‐dihydro‐1H‐pyrrole (2 y) was obtained. With HSbF6 (5 mol %) as the catalyst, polycyclic skeletons 3 and 4 with adjacent

  已经开发了从羟基化的炔烃形成五元杂环化合物的温和而直接的途径。在该反应中，在F 3 CSO 3 H（0.1 mol％）存在的情况下，将羟基化的炔烃选择性地转化为五元杂环化合物2，其烯丙基位于3位。当R 1，R 2 = Ph时，得到二苯基乙烯基-2,3-二氢-1 H-吡咯（2 y）。用HSbF 6（5mol％）作为催化剂，获得具有相邻立构中心的多环骨架3和4。当R 1 = H和R 2时=形成了苯乙烯，1,3-二烯基-2,5-二氢-1 H-吡咯（6 as）。布朗斯台德酸催化的多米诺骨牌工艺涉及形成烯丙基碳阳离子中间体，该中间体很容易被烯烃捕获，从而得到各种新颖的五元杂环骨架。
• Novel Carbon−Carbon Bond Formation from Propargylic Alcohols and Olefin toward Five-Membered Heterocyclic Rings Catalyzed by AgSbF₆
  作者：Ke-Gong Ji、Xing-Zhong Shu、Shu-Chun Zhao、Hai-Tao Zhu、Yan-Ning Niu、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/ol901270b

  日期：2009.8.6

  A mild and direct process for C−C bond formation from propargylic alcohols and olefin has been developed in the presence of a silver catalyst. In this reaction, trace amounts of water were necessary and allene alcohols 2 and 1,3-dienes 3 were obtained selectively.

  在银催化剂的存在下，已经开发了由炔丙醇和烯烃形成C-C键的温和而直接的方法。在该反应中，需要痕量的水，并且选择性地获得烯丙醇2和1，3-二烯3。
• Palladium-catalyzed cycloisomerisation reaction of 1,6-enyne acetic esters to form five-membered nitrogenated heterocyclic conjugated trienes
  作者：Ting He、Pin Gao、Shan Fang、Yaling Chi、Yuantao Chen

  DOI：10.1016/j.tetlet.2017.11.018

  日期：2017.12

  cycloisomerisation reaction of 1,6-enyne acetic esters have been developed. This cyclization reaction shows excellent regioselectivity and good functional group tolerance to obtain five-membered nitrogenated heterocyclic conjugated trienes in moderate to excellent yields. The resulting conjugated trienes could be facilely converted to highly substituted benzenes through Diels-Alder reactions.

  已经开发了钯催化的1，6-烯炔乙酸酯的环异构化反应。该环化反应显示出优异的区域选择性和良好的官能团耐受性，以中等至优异的产率获得了五元氮化杂环共轭三烯。所得的共轭三烯可通过狄尔斯-阿尔德反应容易地转化为高度取代的苯。
• Palladium-Catalyzed Divergent Reactions of 1,6-Enyne Carbonates: Synthesis of Vinylidenepyridines and Vinylidenepyrrolidines
  作者：Shu-Chun Zhao、Ke-Gong Ji、Lei Lu、Ting He、An-Xi Zhou、Ru-Long Yan、Shaukat Ali、Xue-Yuan, Liu、Yong-Min Liang

  DOI：10.1021/jo202590w

  日期：2012.3.16

  A method for preparing five- or six-membered heterocyclic compounds from enyne carbonates via palladium catalysis was developed. Enyne carbonates were transformed into 3-vinylidene-1-tosylpyridines 2 in the presence of PdI2 as the catalyst. Using Pd(dba)(2) as the catalyst, 3-vinylidene-1-tosylpyrrolidines 3 were obtained. Further functionalizations of compounds 3 were carried out in a one-pot manner.