N-[4-(benzyloxy)phenethyl]-N-(3,4-dimethoxybenzyl)trifluoroacetamide | 180200-24-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: N-[4-(benzyloxy)phenethyl]-N-(3,4-dimethoxybenzyl)trifluoroacetamide
• 英文别名: N-[(3,4-dimethoxyphenyl)methyl]-2,2,2-trifluoro-N-[2-(4-phenylmethoxyphenyl)ethyl]acetamide
• CAS: 180200-24-2
• 化学式: C₂₆H₂₆F₃NO₄
• 分子量: 473.492
• InChiKey: XWWZICSFEKNQOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[4-(benzyloxy)phenethyl]-N-(3,4-dimethoxybenzyl)trifluoroacetamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 24.0h， 以48%的产率得到11-(benzyloxy)-6-(trifluoroacetyl)-2,3-dimethoxy-5,6,7,8-tetrahydrodibenz[c,e]azocine
  参考文献：
  名称：

  An Oxidative Intramolecular Phenolic Coupling Reaction for the Synthesis of Amaryllidaceae Alkaloids Using a Hypervalent Iodine(III) Reagent

  摘要：

  The oxidative intramolecular phenolic coupling reaction of norbelladine derivatives (1) was investigated with the aim of preparing amaryllidaceae alkaloids. Spirodienone compounds (2), which are intermediates for the synthesis of an amaryllidaceae alkaloid, (+)-maritidine, or phenol ether derivatives containing the 5,6,7,8-tetrahydrobenzazocine systems (9), were selectively obtained by the reaction of 1 and the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). Both p-p' coupling (11) and p-o' coupling spirodienone compounds (12) were obtained by the reaction of phenol derivatives having an alkoxy group at the C-3' position (10) with PIFA.

  DOI：

  10.1021/jo9606766
• 作为产物：
  描述：

  3',4'-dimethyl-N-(trifluoroacetyl)norbelladine 、 溴甲苯 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以97%的产率得到N-[4-(benzyloxy)phenethyl]-N-(3,4-dimethoxybenzyl)trifluoroacetamide
  参考文献：
  名称：

  An Oxidative Intramolecular Phenolic Coupling Reaction for the Synthesis of Amaryllidaceae Alkaloids Using a Hypervalent Iodine(III) Reagent

  摘要：

  The oxidative intramolecular phenolic coupling reaction of norbelladine derivatives (1) was investigated with the aim of preparing amaryllidaceae alkaloids. Spirodienone compounds (2), which are intermediates for the synthesis of an amaryllidaceae alkaloid, (+)-maritidine, or phenol ether derivatives containing the 5,6,7,8-tetrahydrobenzazocine systems (9), were selectively obtained by the reaction of 1 and the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). Both p-p' coupling (11) and p-o' coupling spirodienone compounds (12) were obtained by the reaction of phenol derivatives having an alkoxy group at the C-3' position (10) with PIFA.

  DOI：

  10.1021/jo9606766

文献信息

• A Novel and Useful Oxidative Intramolecular Coupling Reaction of Phenol Ether Derivatives on Treatment with a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid
  作者：Hiromi Hamamoto、Gopinathan Anilkumar、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1002/1521-3765(20021202)8:23<5377::aid-chem5377>3.0.co;2-h

  日期：2002.12.2

  The oxidative intramolecular coupling reaction of phenol ether derivatives (nonphenolic derivatives) on treatment with a novel combination of a hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA), and heteropoly acid (HPA) was studied. Biaryl compounds were obtained in excellent yields on treatment of highly substituted phenol ethers. On the other hand, spirodienones were specifically

  研究了酚醚衍生物（非酚类衍生物）在高价碘试剂，苯基碘双三氟乙酸酯（PIFA）和杂多酸（HPA）的新型组合下的氧化分子内偶联反应。通过处理高度取代的酚醚，可以以极好的收率获得联芳基化合物。另一方面，当优选的芳基偶联位点之一在对位被甲氧基取代时，特异形成螺二烯酮。