3-N-t-butoxycarbonylamino-2-(4-methoxyphenyl)-1-propene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-N-t-butoxycarbonylamino-2-(4-methoxyphenyl)-1-propene
• 英文别名: tert-butyl N-[2-(4-methoxyphenyl)prop-2-enyl]carbamate
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: GJZXCHLNUIQBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基三氟甲烷磺酸苯酯 、 叔丁氧基 N-氨基甲酸丙烯 在 palladium diacetate 1,1'-双(二苯基膦)二茂铁 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以41%的产率得到3-N-t-butoxycarbonylamino-2-(4-methoxyphenyl)-1-propene
  参考文献：
  名称：

  通过高效的Pd-N配位，区域选择性钯催化的β-芳基化伯烯丙胺当量的合成。

  摘要：

  利用芳基三氟甲磺酸酯和钯/ dppf催化体系，可以在Boc和邻苯二甲酰亚胺基保护的烯丙胺的内部β-碳上进行高度区域选择性的Heck芳基化反应，生成芳基化的伯烯丙胺当量。建议用Boc保护的烯丙基仲胺获得很高的区域选择性，这是由于阴离子氮和钯之间的有效配位引起的。利用单模微波辐射可以缩短反应时间，并且在Boc保护的烯丙基酰胺的情况下，可以提高两种贫电子芳基三氟甲磺酸酯的收率。

  DOI：

  10.1021/jo001416y

文献信息

• Regio- and Stereochemical Aspects of the Palladium-Catalyzed Desilylation−Arylation of Substituted Vinylsilanes
  作者：Davide Alvisi、Errol Blart、Bianca Flavia Bonini、Germana Mazzanti、Alfredo Ricci、Paolo Zani

  DOI：10.1021/jo960301k

  日期：1996.1.1

  The palladium-catalyzed desilylation-arylation of substituted vinylsilanes by p-iodoanisole in the presence of bidentate phosphine ligands is described. Apart from enhancing the rate of the reaction considerably, heteroatom-based functional groups in the vinylsilane moiety have a profound influence on the regiochemistry. A catalytic cycle for the chelation-controlled desilylation-arylation reaction

  描述了在二齿膦配体的存在下，通过对碘苯甲醚的钯催化的取代的乙烯基硅烷的甲硅烷基化-芳基化。除了显着提高反应速率外，乙烯基硅烷部分中基于杂原子的官能团对区域化学有深远的影响。提出了涉及五元和六元螯合环的螯合可控制的硅烷化-芳基化反应的催化循环。
• Combining Copper-Catalyzed Hydroboration with Palladium-Catalyzed Suzuki Coupling for the One-pot Synthesis of Arylallylamines under Micellar Conditions
  作者：Pedro A. Horn、Roger K. Braun、Victória G. Isoppo、Jessie S. da Costa、Diogo S. Lüdtke、Angélica V. Moro

  DOI：10.1002/adsc.201700094

  日期：2017.7.3

  we report the one‐pot dual‐metal catalytic synthesis of arylallylamines, by combination of a Cu‐catalyzed hydroboration with a Pd‐catalyzed Suzuki arylation, using a broad range of aryl halides. Importantly, the reaction sequence was entirely performed in water, in the presence of small amounts of SPGS‐550M, without the need of solvent switch or addition of organic co‐solvents, rendering it operationally

  本文中，我们报告了通过广泛使用的芳基卤化物，通过铜催化的硼氢化与钯催化的Suzuki芳基化相结合的单锅双金属催化合成芳基烯丙胺的方法。重要的是，反应顺序完全在水中，有少量SPGS-550M的情况下进行，而无需溶剂转换或添加有机助溶剂，使其操作简单且对环境无害。这种方法学的有用性在药学上重要的化合物萘替芬的简短合成中得到了强调。
• Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines
  作者：Patrícia Prediger、Laís Ferreira Barbosa、Yves Génisson、Carlos Roque Duarte Correia

  DOI：10.1021/jo201105z

  日期：2011.10.7

  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.
• Regioselective Palladium-Catalyzed Synthesis of <i>β</i>-Arylated Primary Allylamine Equivalents by an Efficient Pd−N Coordination
  作者：Kristofer Olofsson、Helena Sahlin、Mats Larhed、Anders Hallberg

  DOI：10.1021/jo001416y

  日期：2001.1.1

  system, can be performed at the internal, beta-carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary allylamine equivalents. The very high regioselectivity obtained with secondary Boc-protected allylamides is suggested to be caused by an efficient coordination between an anionic nitrogen and palladium. Single-mode microwave irradiation has been utilized to shorten the reaction

  利用芳基三氟甲磺酸酯和钯/ dppf催化体系，可以在Boc和邻苯二甲酰亚胺基保护的烯丙胺的内部β-碳上进行高度区域选择性的Heck芳基化反应，生成芳基化的伯烯丙胺当量。建议用Boc保护的烯丙基仲胺获得很高的区域选择性，这是由于阴离子氮和钯之间的有效配位引起的。利用单模微波辐射可以缩短反应时间，并且在Boc保护的烯丙基酰胺的情况下，可以提高两种贫电子芳基三氟甲磺酸酯的收率。