N-(4-bromo-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide | 1439384-18-5

• 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-bromo-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: N-(4-bromo-2-formylphenyl)-4-methyl-N-prop-2-ynylbenzenesulfonamide
• CAS: 1439384-18-5
• 化学式: C₁₇H₁₄BrNO₃S
• 分子量: 392.273
• InChiKey: CDBBURNLEDVPRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-bromo-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 在 双(乙腈)氯化钯(II) 、 copper(l) iodide 、 copper(II) choride dihydrate 、 palladium diacetate 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 乙腈 为溶剂， 反应 3.17h， 生成 (±) 2-(E-6-bromo-3-(chloro(p-tolyl)methylene)-1-tosyl-1,2,3,4-tetrahydroquinolin-4-yl)-2-chloro-1-(naphthalen-2-yl)ethan-1-one
  参考文献：
  名称：

  钯催化的区域选择性顺-氯丙二醛-烯烃插入-氧化氯化级联反应：二氯化四氢喹啉的合成

  摘要：

  涉及钯催化级联过程顺-chloropalladation，分子内的烯烃插入，和氧化C-Cl键形成反应证实为二氯化四氢喹啉的以高收率合成（高达93％）。具有拴系的α，β-不饱和羰基部分的N-炔丙基芳基胺经历区域选择性的顺-氯钯化，然后进行Heck型反应以递送四氢喹啉骨架。第二个氯原子的稀有插入被合理化，包括Pd II / IV催化循环和C-Pd II键的氧化裂解。

  DOI：

  10.1021/acs.orglett.9b01295
• 作为产物：
  描述：

  2-氨基-5-溴苯甲醇 在 吡啶 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 10.5h， 生成 N-(4-bromo-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  钯催化的区域选择性顺-氯丙二醛-烯烃插入-氧化氯化级联反应：二氯化四氢喹啉的合成

  摘要：

  涉及钯催化级联过程顺-chloropalladation，分子内的烯烃插入，和氧化C-Cl键形成反应证实为二氯化四氢喹啉的以高收率合成（高达93％）。具有拴系的α，β-不饱和羰基部分的N-炔丙基芳基胺经历区域选择性的顺-氯钯化，然后进行Heck型反应以递送四氢喹啉骨架。第二个氯原子的稀有插入被合理化，包括Pd II / IV催化循环和C-Pd II键的氧化裂解。

  DOI：

  10.1021/acs.orglett.9b01295

文献信息

• Direct Access to 9-Chloro-1<i>H</i>-benzo[<i>b</i>]furo[3,4-<i>e</i>]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular <i>syn</i>-Oxypalladation/Olefin Insertion/sp²-C–H Bond Activation Cascade
  作者：Muthu Karuppasamy、B. S. Vachan、Perumal Vinoth、Isravel Muthukrishnan、Subbiah Nagarajan、Laura Ielo、Vittorio Pace、Subrata Banik、C. Uma Maheswari、Vellaisamy Sridharan

  DOI：10.1021/acs.orglett.9b01482

  日期：2019.8.2

  4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C–Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.

  建立了一种有效的Pd（II）催化级联方法，用于从具有侧链α的N-炔丙基芳基胺开始合成9-氯-1 H-苯并[ b ]呋喃[3,4- e ]氮杂-1-酮，β-不饱和酯支架。该顺序过程的机制涉及分子内的顺氧基palpalation，随后的烯烃插入和邻位sp 2 -C-Cl键形成反应。这种高原子和步长经济的级联序列在一次合成操作中产生了两个杂环和三个新键。
• Heterogeneous Amberlyst-15-catalyzed synthesis of complex hybrid heterocycles containing [1,6]-naphthyridine under metal-free green conditions
  作者：Isravel Muthukrishnan、B. S. Vachan、Muthu Karuppasamy、A. Eniyaval、C. Uma Maheswari、Subbiah Nagarajan、J. Carlos Menéndez、Vellaisamy Sridharan

  DOI：10.1039/c9ob01256g

  日期：——

  An efficient green protocol for the synthesis of complex hybrid heterocycles containing [1,6]-naphthyridine and coumarin/pyrazole moieties was established, involving an intramolecular [4 + 2] hetero Diels-Alder reaction as the key step. The biologically significant 12,13-dihydro-6H-benzo[h]chromeno[3,4-b][1,6]naphthyridin-6-ones and 6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b][1,6]naphthyridines were synthesized

  建立了一种有效的绿色方案，用于合成含有[1,6]-萘啶和香豆素/吡唑部分的复杂杂合杂环，其中涉及分子内[4 + 2]杂Diels-Alder反应为关键步骤。具有生物学意义的12,13-二氢-6H-苯并[h] chromeno [3,4-b] [1,6]萘啶-6-和6,10-二氢-5H-苯并[h]吡唑并[3，在Amberlyst-存在下，由2-（N-炔丙基氨基）-芳醛和3-氨基香豆素或3-甲基-1-芳基-1H-吡唑-5-胺开始合成4-b] [1,6]萘啶。 PEG-200中的15种催化剂，收率高。一次操作即可轻松获得各种复杂的分子，这些原料包括现成的起始原料，市售的无过渡金属且可回收的催化剂，绿色溶剂的使用，
• Synthesis of (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones by two-step, one-pot gold-catalyzed tandem heterocyclization/Petasis–Ferrier rearrangement of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes
  作者：Ella Min Ling Sze、Ming Joo Koh、Yen Min Tjia、Weidong Rao、Philip Wai Hong Chan

  DOI：10.1016/j.tet.2013.04.069

  日期：2013.7

  A two-step, one-pot synthetic method that relies on gold(I)-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement and Bronsted acid-assisted debenzoxylation of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes to prepare (2)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones efficiently is reported. The reactions proceed rapidly under mild and operationally straightforward conditions for a wide variety of aldehyde substrates containing electron-withdrawing, electron-donating, and sterically demanding functional groups and afforded the corresponding benzo-fused azaheterocyclic products in moderate to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of 5,6-Dihydrodibenzo[<i>b</i>,<i>h</i>][1,6]naphthyridines via Copper Bromide Catalyzed Intramolecular [4 + 2] Hetero-Diels–Alder Reactions
  作者：Isravel Muthukrishnan、Perumal Vinoth、Thavaraj Vivekanand、Subbiah Nagarajan、C. Uma Maheswari、J. Carlos Menéndez、Vellaisamy Sridharan

  DOI：10.1021/acs.joc.5b02669

  日期：2016.2.5

  A highly efficient synthesis of 5,6-dihydrodibenzo[b,h] [1,6]naphthyridines was achieved by reaction between 2-(N-propargylamino)benzaldehydes and arylamines in the presence of CuBr2. The in situ generated electron-deficient heterodienes bearing a tethered alkyne partner underwent an intramolecular inverse electron-demand hetero-Diels Alder reaction followed by air oxidation to furnish the products in high yields. This reaction tolerated a large number of substituents to afford diverse products under mild conditions. This strategy was also successfully extended to the synthesis of 12,13-dihydro-6-Hbenzo[h]chromeno[3,4-b][1,6]naphthyridin-6-ones starting from 3-amino-2H-chromen-2-one, again in high yields.
• Palladium-Catalyzed Regioselective <i>Syn</i>-Chloropalladation–Olefin Insertion–Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
  作者：Perumal Vinoth、Muthu Karuppasamy、B. S. Vachan、Isravel Muthukrishnan、C. Uma Maheswari、Subbiah Nagarajan、Vittorio Pace、Alexander Roller、Nattamai Bhuvanesh、Vellaisamy Sridharan

  DOI：10.1021/acs.orglett.9b01295

  日期：2019.5.3

  involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C–Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline

  涉及钯催化级联过程顺-chloropalladation，分子内的烯烃插入，和氧化C-Cl键形成反应证实为二氯化四氢喹啉的以高收率合成（高达93％）。具有拴系的α，β-不饱和羰基部分的N-炔丙基芳基胺经历区域选择性的顺-氯钯化，然后进行Heck型反应以递送四氢喹啉骨架。第二个氯原子的稀有插入被合理化，包括Pd II / IV催化循环和C-Pd II键的氧化裂解。