(E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine | 1286169-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine
• 英文别名: (E)-di-tert-butyl 3-(4-methoxyphenyl)allyliminodicarbonate；tert-butyl N-[(E)-3-(4-methoxyphenyl)prop-2-enyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 1286169-82-1
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: TYWFASCCOJTVIS-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  叔丁氧基 N-氨基甲酸丙烯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 sodium acetate 作用下， 以 四氢呋喃 、 苯甲腈 为溶剂， 反应 1.25h， 生成 (E)-N,N-bis(tert-butoxycarbonyl)-3-(4-methoxyphenyl)prop-2-en-1-amine
  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

• Palladium-catalyzed highly regioselective and stereoselective arylation of electron-rich allylamines with aryl bromides
  作者：Zhen Jiang、Lingjuan Zhang、Chaonan Dong、Baode Ma、Weijun Tang、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1016/j.tet.2012.02.081

  日期：2012.6

  excellent yields. It was found that the choice of solvent, olefin, additive and temperature has an important influence on the reaction. Worthy of note is that good results were observed only when using N,N-diprotected allylamines containing carbamate moiety, and the steric properties of allylamines also have important impacts on the regiocontrol. The use of TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) or HQ

  在无配体的条件下，已开发出钯催化的，富电子的N，N-二保护烯丙基胺衍生物与各种芳基溴化物的高效Heck芳基化反应。在Pd（OAc）2和合适的添加剂存在下，反应以极好的区域选择性和立体选择性进行，从而仅以良好的产率至优异的产率产生了γ-芳基化的（E）-烯丙胺产物。发现溶剂，烯烃，添加剂和温度的选择对反应有重要影响。值得注意的是，仅当使用N，N时，才能观察到良好的结果。-含有氨基甲酸酯部分的双保护的烯丙胺，以及烯丙胺的空间性质也对区域控制具有重要影响。使用TEMPO（2,2,6,6-四甲基-1-哌啶基氧基）或HQ（对苯二酚）作为添加剂对于确保更快的反应速度也至关重要。该方法提供了一种直接合成各种γ-芳基化，线性（E）-烯丙胺的直接方法。
• Palladium-Catalyzed, Highly Efficient, Regiocontrolled Arylation of Electron-Rich Allylamines with Aryl Halides
  作者：Yuheng Deng、Zhen Jiang、Min Yao、Dan Xu、Lingjuan Zhang、Huanrong Li、Weijun Tang、Lijin Xu

  DOI：10.1002/adsc.201100835

  日期：2012.3.16

  and regioselective palladium‐catalyzed Heck coupling of aryl bromides with electron‐rich allylamine derivatives is described. It was found that the choice of solvent, olefin, ligand and additive had a fundamental influence on the regioselectivity and reactivity of the reaction. The combination of palladium acetate [Pd(OAc)2] and 1,3‐bis(diphenylphosphino)propane (dppp) in ethylene glycol (EG) constitutes

  描述了芳基溴化物与富电子烯丙基胺衍生物的高效和区域选择性钯催化的Heck偶联。发现溶剂，烯烃，配体和添加剂的选择对反应的区域选择性和反应性具有根本影响。乙二醇（EG）中乙酸钯[Pd（OAc）2 ]和1,3-双（二苯基膦基）丙烷（dppp）的组合构成了N -Boc-烯丙胺（叔丁基）内部芳基化的高效催化剂体系芳基二碳酸二甲酯）与芳基溴化物具有良好的区域选择性，而催化剂体系由Pd（OAc）2组成铵，四丁基溴化铵（TBAB）和2,2,6,6-四甲基-1-哌啶氧（TEMPO）添加剂允许多种芳基溴化物的与有效地反应Ñ，ñ - （BOC）2 -allylamine（二-叔-水中的烯丙基二碳酸二丁酯）以高产率专门提供线性（E）-烯丙胺产品。
• 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.