N-(4-methoxybenzyl)buta-2,3-dien-1-amine | 1301169-45-8

• 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-methoxybenzyl)buta-2,3-dien-1-amine
• CAS: 1301169-45-8
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: MCQDIVMSLDLSNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)buta-2,3-dien-1-amine 在 palladium diacetate 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 42.0h， 生成 (4S,8aS)-4-(1-(3-chloro-4-methylphenyl)vinyl)-2-(4-methoxybenzyl)hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one
  参考文献：
  名称：

  通过金属催化的丙二烯环合成脯氨酸衍生的双环衍生物：长酰胺B，苯乙烯基丁烯D及其衍生物的合成

  摘要：

  过渡金属促进的丙二烯取代的脯氨酸衍生物环化提供了对溴吡咯生物碱的获取。已经研究了Pd和Ag催化的两个环化过程，它们互补地用于控制双环产物的取代模式。该方法已应用于合成长酰胺B苯甲酰D及其衍生物

  DOI：

  10.1002/ejoc.201901554
• 作为产物：
  描述：

  (4-甲氧基苄基)2-丙炔基-1-基胺 1盐酸盐 在 盐酸 、 二异丙胺 、 copper(I) bromide 作用下， 以 乙醚 、 水 、 甲苯 为溶剂， 反应 25.0h， 生成 N-(4-methoxybenzyl)buta-2,3-dien-1-amine
  参考文献：
  名称：

  Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts

  摘要：

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.

  DOI：

  10.1021/acs.orglett.5b00809

文献信息

• Highly regioselective three-component palladium-catalyzed synthesis of 5-vinyloxazolidin-2-ones from 2,3-allenyl amines, organic iodides, and carbon dioxide
  作者：Suhua Li、Juntao Ye、Weiming Yuan、Shengming Ma

  DOI：10.1016/j.tet.2013.09.087

  日期：2013.12

  A highly regioselective Pd(0)-catalyzed synthesis of 5-vinyloxazolidin-2-ones from 2,3-allenic amines, organic iodides, and CO2 under mild conditions has been developed.

  甲高度选择性的Pd（0） -催化的5- vinyloxazolidin -2-酮由2,3-丙二烯胺类，有机碘化物，和CO的合成2温和的条件下得到了发展。
• Palladium-Catalyzed Three-Component Reaction of 2,3-Allenyl Amines, Isocyanates, and Organic Halides: A Diversified Assembly of Imidazolidinones
  作者：Wei Shu、Qiong Yu、Guochen Jia、Shengming Ma

  DOI：10.1002/chem.201003611

  日期：2011.4.18

  A three‐component reaction of 2,3‐allenyl amines with isocyanates and organic halides has been developed. Two carbon–nitrogen bonds as well as a carbon–carbon bond were sequentially formed to construct imidazolidinone derivatives in good to excellent yields (see scheme).

  已经开发了2,3-烯丙基胺与异氰酸酯和有机卤化物的三组分反应。依次形成两个碳-氮键以及一个碳-碳键，以高到极好的收率构建咪唑啉酮衍生物（参见方案）。
• Palladium-Catalyzed Cyclization Reactions of 2,3-Allenyl Amines with Propargylic Carbonates
  作者：Juntao Ye、Suhua Li、Shengming Ma

  DOI：10.1021/ol3007293

  日期：2012.5.4

  A highly efficient and atom-economic route to synthesize 5-(1,3,4-alkatrien-2-yl)oxazolidin-2-ones via palladium-catalyzed cyclization reactions of 2,3-allenyl amines with propargylic carbonates was reported. The CO2 generated in situ from propargylic carbonates is incorporated into the oxazolidin-2-one unit with high efficiency, affording the products in 70–92% yields.

  据报道，通过钯催化的2,3-烯基胺与碳酸炔丙基酯的环化反应，可以合成5-（1,3,4-烷基三烯-2-基）恶唑烷-2-酮的高效且经济的路线。由炔丙基碳酸酯原位产生的CO 2被高效地引入到恶唑烷-2-一单元中，从而使产物的收率达到70-92％。
• Modular Synthesis of Cyclopropane‐Fused <i>N</i> ‐Heterocycles Enabled by Underexplored Diazo Reagents
  作者：Matthieu J. R. Richter、Frédéric J. Zécri、Karin Briner、Stuart L. Schreiber

  DOI：10.1002/anie.202203221

  日期：2022.9.19

  Modular synthesis of cyclopropane-fused N-heterocycles from readily available amines was achieved. Key to the disclosed strategy was the development and implementation of reactive α-diazo acylating agents, providing access to structurally and functionally diverse products. Application of the method is showcased in the concise syntheses of therapeutic agents milnaciprane and amitifadine.

  从容易获得的胺中实现了环丙烷稠合的N-杂环的模块化合成。所公开策略的关键是反应性α-重氮酰化剂的开发和实施，提供结构和功能多样化的产品。该方法在治疗药物米那普兰和阿米替发定的简明合成中得到应用。
• Highly Selective Carboxylative Cyclization of Allenylmethylamines with Carbon Dioxide Using N-Heterocyclic Carbene-Silver(I) Catalysts
  作者：Kyohei Yamashita、Shun Hase、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1021/acs.orglett.5b00809

  日期：2015.5.15

  Silver(I) carboxylate complexes promote the carboxylative cyclization of allenylmethylamines to afford 5-alkenyl-1,3-oxazolidin-2-ones in 2-propanol. The use of an N-heterocyclic carbene ligand (IPr) under pressurized CO2 is effective in suppressing the intramolecular hydroamination that leads to 2,5-dihydropyrroles. The mechanism involving a nucleophilic attack of the carbamate of the allene moiety and a subsequent protonation was realized on the basis of experimental and theoretical results involving a model intermediate, the alkenylgold(I) complex, which was synthesized from Au(OH)(IPr) and 1-methylamino-2,3-butadiene.