4,5-dimethyl-2-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine | 125486-82-0

• 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: 4,5-dimethyl-2-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine
• 英文别名: 4,5-dimethyl-1-(4-methylphenyl)sulfonyl-2-phenyl-3,6-dihydro-2H-pyridine
• CAS: 125486-82-0
• 化学式: C₂₀H₂₃NO₂S
• 分子量: 341.474
• InChiKey: WSODIGURDXKJGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-亚硫酰基-p-甲苯磺胺 在 三氟化硼乙醚 、 magnesium sulfate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.08h， 生成 4,5-dimethyl-2-phenyl-1-tosyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  A convenient in situ procedure for effecting inter- and intramolecular Diels-Alder reactions of N-sulfonyl imines

  摘要：

  DOI：

  10.1016/s0040-4039(00)99396-1

文献信息

• Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines
  作者：Yasuo Hatanaka、Shuuto Nantaku、Yuhki Nishimura、Tomoyuki Otsuka、Tohru Sekikaw

  DOI：10.1039/c7cc03010j

  日期：——

  A catalytic enantioselective aza-Diels–Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5–10 mol% loadings of a new Brønsted acid catalyst, the aza-Diels–Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels–Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee)

  描述了未活化的无环二烯与芳基，烯基和烷基取代的亚胺的催化对映选择性氮杂-Diels-Alder反应。在新布朗斯台德酸催化剂的负载量为5-10 mol％的情况下，未活化的无环二烯的aza-Diels-Alder反应以高收率（高达98％）得到相应的aza-Diels-Alder加合物，具有出色的对映选择性（高达到98％ee）。初步的DFT计算表明该反应通过手性离子对中间体进行。
• Carbocations as Lewis Acid Catalysts: Reactivity and Scope
  作者：Juho Bah、Veluru Ramesh Naidu、Johannes Teske、Johan Franzén

  DOI：10.1002/adsc.201400609

  日期：2015.1.12

  of potential Lewis acids that has received negligible attention as a catalyst is the carbocation. Here we show the potential of triarylmethylium ions as highly powerful Lewis acid catalysts for organic reactions. The Lewis acidity of the triarylmethylium ion can be easily tuned by variation of the electronic properties of the aromatic rings and the catalytic activity of the carbocation is shown to correlate

  碳阳离子是一类潜在的路易斯酸，已被忽略不计，它是一种催化剂。在这里，我们展示了三芳基甲基离子作为有机反应的强力路易斯酸催化剂的潜力。三芳基甲基离子的路易斯酸度可以通过改变芳环的电子性质而容易地调节，并且碳正离子的催化活性显示出与阳离子碳上的空p C轨道的稳定水平直接相关。三芳基甲基离子作为有机反应的有效路易斯酸催化剂的多功能性已在Diels–Alder，Aza–Diels–Alder，共轭加成，卤化，环氧重排和分子内异戊烯反应中得到证明。
• FeCl₃ as an Ion-Pairing Lewis Acid Catalyst. Formation of Highly Lewis Acidic FeCl₂⁺ and Thermodynamically Stable FeCl₄^– To Catalyze the Aza-Diels–Alder Reaction with High Turnover Frequency
  作者：Rei Tomifuji、Kazuki Maeda、Toshifumi Takahashi、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/acs.orglett.8b03249

  日期：2018.12.7

  provided fundamental insights into the disproportionation and structure of the resulting ion-paired iron complex. A theoretical study was performed to analyze the catalytic reaction and better understand the “ion-pairing effect” which transforms simple FeCl3 into a high turnover frequency Lewis acid catalyst in the aza-Diels–Alder reaction of nonactivated dienes and imines.

  非活化二烯和亚胺的aza-Diels-Alder反应是通过FeCl 3原位歧化产生的离子对路易斯酸催化剂[FeCl 2 ] + [FeCl 4 ] -的作用实现的。[FeCl 2 ] + [FeCl 4 ] -的独特高反应性归因于高路易斯酸性FeCl 2 +和热力学稳定的FeCl 4 –充当离子对催化剂。基于同步加速器的X射线吸收精细结构测量提供了对所得离子配对铁配合物的歧化和结构的基本认识。进行了理论研究以分析催化反应并更好地理解“离子对效应”，该效应将简单的FeCl 3转化为非活化二烯和亚胺的aza-Diels-Alder反应中的高周转率路易斯酸催化剂。
• Cobalt(III) Porphyrin Catalyzed Aza-Diels–Alder Reaction
  作者：Ryota Wakabayashi、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ol3020946

  日期：2012.9.21

  An efficient protocol for the aza-Diels-Alder reaction of electron-deficient 1,3-dienes with unactivated imines in the presence of a cationic cobalt(III) porphyrin complex was developed. The transformation proceeded smoothly to afford the desired piperidine scaffold within 2 h at ambient temperature. Highly chemoselective cycloaddition of imines with dienes in the presence of a variety of carbonyl compounds was also demonstrated.
• One-pot Diels-Alder reaction of N-p-tosylaldimines generated by BF3Et2O catalyzed transformation of naphtho[1,8-de]dithiin-1-N-p-tosylsulfilimines
  作者：Takayoshi Fujii、Takeshi Kimura、Naomichi Furukawa

  DOI：10.1016/0040-4039(95)00901-n

  日期：1995.7