N-(p-toluenesulfonyl)-1-amino-1-(cyclohexyl)prop-2-yne | 181020-94-0

• 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: N-(p-toluenesulfonyl)-1-amino-1-(cyclohexyl)prop-2-yne
• 英文别名: N-(1-cyclohexyl-2-propyn-1-yl)-4-methyl-benzenesulfonamide；N-(1-cyclohexylprop-2-ynyl)-4-methylbenzenesulfonamide
• CAS: 181020-94-0
• 化学式: C₁₆H₂₁NO₂S
• 分子量: 291.414
• InChiKey: HGXNPVWAPQFYEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-(p-toluenesulfonyl)-1-amino-1-(cyclohexyl)prop-2-yne 在 palladium diacetate 、 偶氮二甲酸二异丙酯 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 (+/-)-1-cyclohexyl-2-(4-methylphenylsulfonyl)-2,3-dihydro-1H-benzo[f]isoindole
  参考文献：
  名称：

  通过芳族CH键官能化，钯催化溴代炔的串联环化。

  摘要：

  DOI：

  10.1002/anie.200500159
• 作为产物：
  描述：

  tert-butyl N-(1-cyclohexylprop-2-ynyl)-N-(4-methylphenyl)sulfonylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以89%的产率得到N-(p-toluenesulfonyl)-1-amino-1-(cyclohexyl)prop-2-yne
  参考文献：
  名称：

  Inter- and Intramolecular Addition/Cyclizations of Sulfonamide Anions with Alkynyliodonium Triflates. Synthesis of Dihydropyrrole, Pyrrole, Indole, and Tosylenamide Heterocycles

  摘要：

  The synthesis of dihydropyrroles, pyrroles, and indoles through [3-atom $ 2-atom] combination of ethyl or aryl tosylamide anions with phenyl(propynyl)iodonium triflate, and the base-mediated intramolecular bicyclization of alkynyliodonium-bearing tosylamide or tosylimide substrates to furnish bicyclic and tricyclic tosylenamide (-enimide) products, is described. A detailed discussion of the scope, limitations, byproduct formation, and the basis for observed diastereoselectivity is presented.

  DOI：

  10.1021/jo9605814

文献信息

• Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis–Cyclization Reaction
  作者：Helene Chachignon、Nicolò Scalacci、Elena Petricci、Daniele Castagnolo

  DOI：10.1021/acs.joc.5b00222

  日期：2015.5.15

  Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted

  炔丙基胺与乙基乙烯基醚的烯炔交叉易位能够一锅合成取代的吡咯。在微波辐射下，以高收率合成了一系列带有烷基，芳基和杂芳基取代基的取代吡咯。该反应是快速的并且程序上简单的，并且也代表了容易合成的具有挑战性的1,2,3-取代的吡咯的入口。通过将吡咯转化为3-甲基吡咯啉以及由复分解反应引起的3-甲基取代基的衍生化，进一步证实了该方法学的价值。
• Redox-Neutral Synthesis of β-Amino Aldehydes from Imines by an Alkynylation/Hydration Sequence
  作者：Aurélie Labonne、Lorenzo Zani、Lukas Hintermann、Carsten Bolm

  DOI：10.1021/jo070745o

  日期：2007.7.1

  N-Protected beta-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of the latter reaction are enhanced by the use of microwave irradiation. The possibility to carry out a one-pot Ru-catalyzed hydration/oxidation process from a terminal alkyne to a carboxylic acid was demonstrated, which provided direct access to a N-protected beta-amino acid from the corresponding terminal alkyne.