N-[1-(4-methoxyphenyl)-prop-2-ynyl]-4-methyl-benzenesulfonamide | 771565-23-2

• 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-[1-(4-methoxyphenyl)-prop-2-ynyl]-4-methyl-benzenesulfonamide
• 英文别名: N-(p-toluenesulfonyl)-1-amino-1-(4-methoxyphenyl)prop-2-yne；N-[1-(4-methoxyphenyl)prop-2-yn-1-yl]-4-methylbenzenesulfonamide；N-[1-(4-methoxyphenyl)prop-2-ynyl]-4-methylbenzenesulfonamide
• CAS: 771565-23-2
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: CFUBURBGQZBOTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[1-(4-methoxyphenyl)-prop-2-ynyl]-4-methyl-benzenesulfonamide 在 (η⁵-cyclopentadienyl) (η⁶-naphthalene)ruthenium hexafluorophosphate 水 作用下， 以 丙酮 为溶剂， 反应 15.0h， 以83%的产率得到N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)propanal
  参考文献：
  名称：

  Redox-Neutral Synthesis of β-Amino Aldehydes from Imines by an Alkynylation/Hydration Sequence

  摘要：

  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.

  DOI：

  10.1021/jo070745o
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 tetrafluoroboric acid 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 18.0h， 生成 N-[1-(4-methoxyphenyl)-prop-2-ynyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  HBF4 催化的丙炔醇的亲核取代

  摘要：

  介绍了 HBF4（水溶液）在炔丙基化反应中作为催化剂的活性。为了在工业丙酮和空气中形成新的 C-O、C-N 和 C-C 键，使用了不同类型的亲核试剂。在简单的反应条件下使用低酸负载量（通常为 1 mol%）可获得良好至极好的产率和良好的化学选择性。

  DOI：

  10.1002/ejoc.201501249

文献信息

• Gold(I)-Catalyzed Tandem Reaction of<i>γ</i>-Amino-Substituted Propargylic Esters to Pyrrolines and its Application in the Formal Synthesis of (±)-Aphanorphine
  作者：Zhengshen Wang、Huaiji Zheng、Juan Yang、Xingang Xie、Xuegong She

  DOI：10.1002/adsc.201401161

  日期：2015.6.15

  effective synthesis of structurally diverse pyrroline derivatives has been accomplished by a gold(I)‐catalyzed tandem 1,3‐acyloxy rearrangement/intramolecular azacylization reaction of γ‐amino‐substituted propargylic esters in good to excellent chemical yields (52–98%). The reaction proceeds under extremely mild conditions and has also demonstrated its potential in a concise formal synthesis of (±)‐aphanorphine

  通过金（I）催化的γ-氨基取代的炔丙基酯的串联1,3-酰氧基重排/分子内氮氧化反应，可以有效地合成结构多样的吡咯啉衍生物，化学收率良好（52-98％） 。该反应在极其温和的条件下进行，并且已经证明了其在简明形式的（±）-甲啡肽的简明合成中的潜力，该催化剂的负载量低至0.5 mol％，可提供关键的中间体5-（4-甲氧基苄基）-1-甲苯磺酰基克级的-2,5-二氢-1 H-吡咯-3-基新戊酸酯。
• Copper-Catalyzed Domino Homologation and Cycloisomerization Reactions for 3-Pyrroline Synthesis
  作者：Ye Ho Shin、Muchchintala Maheswara、Joon Young Hwang、Eun Joo Kang

  DOI：10.1002/ejoc.201301621

  日期：2014.4

  catalyst for a domino reaction sequence leading to 3-pyrrolines. The Cu(I)-catalyzed Crabbe reaction of propargyl sulfonamide and selective cycloisomerization of the allene intermediate were carried out using microwave irradiation conditions affording a wide range of 2-substituted- and 2,5-disubstituted-3-pyrrolines. Mechanistic studies of the reaction intermediates revealed two possible reaction pathways;

  发现溴化铜是产生 3-吡咯啉的多米诺反应序列的有效催化剂。Cu(I) 催化炔丙基磺酰胺的 Crabbe 反应和丙二烯中间体的选择性环异构化是使用微波辐射条件进行的，提供了广泛的 2-取代-和 2,5-二取代-3-吡咯啉。反应中间体的机理研究揭示了两种可能的反应途径；两者都提到了乙烯基铜中间体的重要性。
• The Coupling-Isomerization Approach to Enimines and the First Sequential Three-Component Access to 2-Ethoxy Pyridines
  作者：Oana G. Dediu、Nasser A. M. Yehia、Thomas J. J. Müller

  DOI：10.1515/znb-2004-0413

  日期：2004.4.1

  The coupling-isomerization reaction (CIR) of electron-deficient halides 1 with N-[1-(hetero)arylprop-2-ynyl] tosyl amides 2 leads to the formation of N-tosyl enimines 3, in good to excellent yields. These electron deficient heterodienes are perfectly suited for Diels-Alder reactions with inverse electron demand. In the sense of a one-pot reaction a three-component CIR-cyclocondensation sequence of 1, 2a, and diethyl ketene acetal gives rise to the formation of 2-ethoxy 6-(p-anisyl)pyridines 4 in moderate to good yields.

  摘要：电子亏缺卤代物1与N-[1-(杂)芳基丙炔基]对甲苯磺酰胺2的偶联-异构化反应（CIR）可高产率地形成N-对甲苯磺酰亚胺3。这些电子亏缺的异构二烯非常适合反电子需求的Diels-Alder反应。在一锅反应的意义上，1、2a和乙酸乙酯缩醛的三组分CIR-环缩合序列可形成2-乙氧基6-(对甲氧基苯基)吡啶4，收率中等至良好。
• Coupling-Isomerization−<i>N</i>,<i>S</i>-Ketene Acetal-Addition SequencesA Three-Component Approach to Highly Fluorescent Pyrrolo[2,3-<i>b</i>]pyridines, [1,8]Naphthyridines, and Pyrido[2,3-<i>b</i>]azepines
  作者：Oana G. Schramm、née Dediu、Thomas Oeser、Thomas J. J. Müller

  DOI：10.1021/jo0602726

  日期：2006.4.1

  Annelated 2-amino pyridines such as pyrrolo[2,3-b]pyridines, [1,8]naphthyridines, and pyrido[2,3-b]azepines can be synthesized in moderate to good yields in a consecutive one-pot three-component process by a coupling-isomerization-enamine-addition-cyclocondensation sequence of an electron-poor (hetero)aryl halide, a terminal propargyl N-tosylamine, and an N,S-ketene acetal. After the coupling-isomerization sequence, a Diels-Alder reaction with inverse electron demand of the intermediate enimine and the N,S-ketene acetal and subsequent aromatization furnish annelated 2-amino pyridines 4 that were unambiguously characterized by numerous X-ray structure analyses. These heterocycles are highly fluorescent and partially pH sensitive, and their electronic structure was studied with spectroscopic and computational methods.