N-(3-allyl-4-(allyloxy)phenyl)acetamide | 861295-49-0

• 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-(3-allyl-4-(allyloxy)phenyl)acetamide
• 英文别名: 5-Acetamino-2-allyloxy-1-allyl-benzol；4-Acetamino-2-allyl-phenol-allylaether；N-(3-Allyl-4-allyloxy-phenyl)-acetamid；N-(4-prop-2-enoxy-3-prop-2-enylphenyl)acetamide
• CAS: 861295-49-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: YKEGFYHFNRGLSX-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C
• 沸点：
  397.7±42.0 °C(predicted)
• 密度：
  1.055±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-allyl-4-(allyloxy)phenyl)acetamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 盐酸 、 [RuHCl(CO)(PPh₃)₃] 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 1-苯并呋喃-5-胺
  参考文献：
  名称：

  芳族重氮盐的Matsuda-Heck偶联合成苯丙烷

  摘要：

  Pd催化的富电子芳烃重氮盐与缺电子烯烃的Heck型偶联（Matsuda–Heck反应）已被用于合成苯丙天然产物。本文所述的实例是天然存在的苯并呋喃五氟呋喃酸甲酯，五氢呋喃醇，五氟呋喃醛，它们的7-甲氧基衍生物以及O-炔丙基化的天然产物硼松酚A和C。

  DOI：

  10.1021/acs.joc.7b00447
• 作为产物：
  描述：

  3-(2-hydroxy-5-aminophenyl)-1-propene 在 potassium carbonate 、 丙酮 作用下， 生成 N-(3-allyl-4-(allyloxy)phenyl)acetamide
  参考文献：
  名称：

  Claisen, Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102

  摘要：

  DOI：

文献信息

• Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors
  作者：Atena Jabbari、Mahdieh Davoodnejad、Maliheh Alimardani、Amir Assadieskandar、Ali Sadeghian、Hadi Safdari、Jebraeel Movaffagh、Hamid Sadeghian

  DOI：10.1016/j.bmc.2012.07.025

  日期：2012.9

  15-Lipoxygenases are one of the nonheme iron-containing proteins with ability of unsaturated lipid peroxidation in animals and plants. The critical role of the enzymes in formation of inflammations, sensitivities and some of cancers has been demonstrated in mammalians. Importance of the 15-lipoxygenases leads to development of mechanistic studies, products analysis and synthesis of their inhibitors. In this work new series of the 3-allyl-4-allyoxyaniline amides and 3-allyl-4-prenyloxyaniline amides were designed, synthesized and their inhibitory potency against soybean 15-lipoxygenase were determined. Among the synthetic amides, 3-allyl-4-(farnesyloxy)-adamantanilide showed the most potent inhibitory activity by IC50 value of 0.69 mu M. SAR studies showed that in spite of prenyl length increases, the effects of the amide size and its electronic properties on the inhibitory potency became predominant. The SAR studies was also showed that the orientation of allyl and prenyloxy moieties toward Fe core of the SLO active site pocket is the most suitable location for enzyme inhibition. (C) 2012 Elsevier Ltd. All rights reserved.
• Claisen, Justus Liebigs Annalen der Chemie, 1919, vol. 418, p. 102
  作者：Claisen

  DOI：——

  日期：——
• Synthesis of Phenylpropanoids via Matsuda–Heck Coupling of Arene Diazonium Salts
  作者：Bernd Schmidt、Felix Wolf

  DOI：10.1021/acs.joc.7b00447

  日期：2017.4.21

  The Pd-catalyzed Heck-type coupling (Matsuda–Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A

  Pd催化的富电子芳烃重氮盐与缺电子烯烃的Heck型偶联（Matsuda–Heck反应）已被用于合成苯丙天然产物。本文所述的实例是天然存在的苯并呋喃五氟呋喃酸甲酯，五氢呋喃醇，五氟呋喃醛，它们的7-甲氧基衍生物以及O-炔丙基化的天然产物硼松酚A和C。