(E)-4-methyl-N-(3-(naphthalen-2-yl)allyl)benzenesulfonamide | 1334031-86-5

• 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: (E)-4-methyl-N-(3-(naphthalen-2-yl)allyl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(E)-3-naphthalen-2-ylprop-2-enyl]benzenesulfonamide
• CAS: 1334031-86-5
• 化学式: C₂₀H₁₉NO₂S
• 分子量: 337.442
• InChiKey: LZGIBTYVEXOOFL-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (E)-4-methyl-N-(3-(naphthalen-2-yl)allyl)benzenesulfonamide 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以476 mg的产率得到(E)-4-methyl-N-(3-(naphthalen-2-yl)allyl)-N-(prop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  全金属芳族三钯配合物和羧酸催化的1,6-烯炔分子间/分子内级联反应

  摘要：

  三核全金属芳族簇是一类具有环状和平面金属核的原始分子。它们以特殊的金属-金属离域键为特征，代表了过渡金属催化的新前沿。我们报告了一项由三核全金属芳族钯簇催化的多不饱和底物的 C-C 形成反应的研究。在温和的反应条件下合成了两个具有广泛官能团耐受性的新三环化合物家族。该方法具有独特的区域选择性和非对映选择性，表明三核钯配合物与其流行的单核配合物互补。此外，对这些多环化反应机理的初步研究揭示了均相催化体系的独特特征。

  DOI：

  10.1021/acs.joc.1c01962
• 作为产物：
  描述：

  对甲苯磺酰氯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 苯甲腈 为溶剂， 反应 24.0h， 生成 (E)-4-methyl-N-(3-(naphthalen-2-yl)allyl)benzenesulfonamide
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z

文献信息

• Highly Enantioselective Nickel-Catalyzed Intramolecular Hydroalkenylation of N- and O-Tethered 1,6-Dienes To Form Six-Membered Heterocycles
  作者：Ke Li、Mao-Lin Li、Qi Zhang、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/jacs.8b04703

  日期：2018.6.20

  A highly enantioselective nickel-catalyzed intramolecular hydroalkenylation of N- or O-tethered 1,6-dienes was developed by using monodentate chiral spiro phosphoramidite ligands. The reaction provides an efficient and straightforward method for preparing very useful six-membered N- and O-heterocycles with high regioselectivity as well as excellent stereoselectivity from easily accessible starting

  通过使用单齿手性螺亚磷酰胺配体开发了高度对映选择性镍催化的 N 或 O 系链 1,6-二烯的分子内加氢烯基化。该反应提供了一种有效且直接的方法，可以在温和的反应条件下从易于获得的起始材料中制备非常有用的六元 N-和 O-杂环，具有高区域选择性和优异的立体选择性。本研究中开发的手性螺镍催化剂是为数不多的用于非共轭二烯高度对映选择性环化的催化剂之一。
• Correction to “Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of <i>trans</i>-1,2-Disubstituted Alkenes”
  作者：Caiyou Chen、Shicheng Jin、Zhefan Zhang、Biao Wei、Heng Wang、Kai Zhang、Hui Lv、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/jacs.6b13274

  日期：2017.3.22

  mL of toluene, Rh(acac)(CO)2 as the metal precursor, (S,R)-(N-Bn)Yanphos as the ligand, CO:H2 = 10:10 bar, S/C = 20, HSiEt3 (0.3 mmol), and BF3.Et2O (0.3 mmol) The configuration of all of the products was determined to be S, except for 4m; only the desired regioisomer was obtained as determined by NMR analysis. Scheme 4. Synthetic Transformations Addition/Correction

  反应以 0.1 mmol 规模在 0.5 mL 甲苯中进行，Rh(acac)(CO)2 作为金属前体，(S,R)-(N-Bn)Yanphos 作为配体，CO:H2 = 10: 10 bar, S/C = 20, HSiEt3 (0.3 mmol), and BF3.Et2O (0.3 mmol) 通过NMR分析确定仅获得所需的区域异构体。方案 4. 合成变换加法/校正
• Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of <i>trans</i>-1,2-Disubstituted Alkenes
  作者：Caiyou Chen、Shicheng Jin、Zhefan Zhang、Biao Wei、Heng Wang、Kai Zhang、Hui Lv、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1021/jacs.6b03596

  日期：2016.7.27

  The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility

  开发了第一个间断的不对称氢氨甲基化反应。具有挑战性的反式-1,2-二取代烯烃被用作底物，并以高产率、高区域选择性和优异的对映选择性获得了一系列有价值的手性吡咯烷酮和吡咯烷。进行了几次合成转化，证明了我们方法的高合成效用。还开发了合成 vernakalant 和 Enablex 的创造性路线。