N-allyl-N-(4-methoxybenzyl)acrylamide | 1429218-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-allyl-N-(4-methoxybenzyl)acrylamide
• 英文别名: N-[(4-methoxyphenyl)methyl]-N-prop-2-enylprop-2-enamide
• CAS: 1429218-11-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: MMLCKRDGMVIKLG-UHFFFAOYSA-N

物化性质

• 沸点：
  397.6±35.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(4-methoxybenzyl)acrylamide 在 titanium(IV) isopropylate 、 Stewart-Grubbs catalyst 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 14.67h， 生成 (E)-3-(5-(5-(benzyloxy)-1H-indol-3-yl)-1-(4-methoxybenzyl)-2-oxo-1H-pyrrol-3(2H)-ylidene)indolin-2-one
  参考文献：
  名称：

  Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

  摘要：

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

  DOI：

  10.1021/ol400654r
• 作为产物：
  描述：

  丙烯酰氯 、 N-allyl-4-methoxybenzylamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以54%的产率得到N-allyl-N-(4-methoxybenzyl)acrylamide
  参考文献：
  名称：

  Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein

  摘要：

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.

  DOI：

  10.1021/ol400654r

文献信息

• Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one by Novel Palladium(II)-Catalyzed Cyclization and Ring-Closing Metathesis
  作者：Subhash Chavan、Ashok Pathak、Kailash Pawar

  DOI：10.1055/s-0034-1379985

  日期：——

  Abstract Synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one is described starting from commercially available allylamine and 4-methoxybenzylamine employing palladium-catalyzed cyclization or ring-closing metathesis as the key steps. Synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one is described starting from commercially available allylamine and 4-methoxybenzylamine employing palladium-catalyzed

  摘要 描述了从商业上可获得的烯丙基胺和4-甲氧基苄基胺开始的3-乙基-4-甲基-1，5-二氢-2 H-吡咯-2-酮的合成，其中钯催化的环化或闭环复分解为关键步骤。 描述了从商业上可获得的烯丙基胺和4-甲氧基苄基胺开始的3-乙基-4-甲基-1，5-二氢-2 H-吡咯-2-酮的合成，其中钯催化的环化或闭环复分解为关键步骤。
• Tandem Ring-Closing Metathesis/Isomerization Reactions for the Total Synthesis of Violacein
  作者：Mette T. Petersen、Thomas E. Nielsen

  DOI：10.1021/ol400654r

  日期：2013.4.19

  A series of 5-substituted 2-pyrrolidinones was synthesized through a one-pot ruthenium alkylidene-catalyzed tandem RCM/isomerization/nucleophilic addition sequence. The intermediates resulting from RCM/isomerization showed reactivity toward electrophiles in aldol condensation reactions which provided a new entry for the total synthesis of the antileukemic natural product violacein.