N-(3,4-dimethoxybenzyl)-N-(4-methoxyphenethyl)trifluoroacetamide | 50479-36-2

• 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-(3,4-dimethoxybenzyl)-N-(4-methoxyphenethyl)trifluoroacetamide
• 英文别名: N-[(3,4-dimethoxyphenyl)methyl]-2,2,2-trifluoro-N-[2-(4-methoxyphenyl)ethyl]acetamide
• CAS: 50479-36-2
• 化学式: C₂₀H₂₂F₃NO₄
• 分子量: 397.394
• InChiKey: MPUUSEOPMDVHBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 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-(3,4-dimethoxybenzyl)-N-(4-methoxyphenethyl)trifluoroacetamide 在 tetrafluoroboric acid 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以73%的产率得到2-(trifluoroacetyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-dien-4'-one
  参考文献：
  名称：

  石蒜科生物碱的通用电合成方法

  摘要：

  高度药学相关的石蒜科生物碱已通过多功能电有机关键转化获得，其中包括乙酰胆碱酯酶抑制剂加兰他敏的前体，该药物被 FDA 批准用作治疗阿尔茨海默病的药物。螺二烯酮型中间体是通过区域选择性和可持续的阳极关键转化从天然原料中获得的

  DOI：

  10.1002/chem.202201523
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成 N-(3,4-dimethoxybenzyl)-N-(4-methoxyphenethyl)trifluoroacetamide
  参考文献：
  名称：

  石蒜科生物碱的通用电合成方法

  摘要：

  高度药学相关的石蒜科生物碱已通过多功能电有机关键转化获得，其中包括乙酰胆碱酯酶抑制剂加兰他敏的前体，该药物被 FDA 批准用作治疗阿尔茨海默病的药物。螺二烯酮型中间体是通过区域选择性和可持续的阳极关键转化从天然原料中获得的

  DOI：

  10.1002/chem.202201523

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。
• Non-phenolic oxidative coupling of phenol ether derivatives using phenyliodine(III) bis(trifluoroacetate)
  作者：Yasuyuki Kita、Michiyo Gyoten、Makoto Ohtsubo、Hirofumi Tohma、Takeshi Takada

  DOI：10.1039/cc9960001481

  日期：——

  Phenol ether derivatives (non-phenolic derivatives), 1,3-diarylpropanes 1a–e, N-benzyl-N-phenethylamines 2a–c and N,N-dibenzylamines 3a–e react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate)(PIFA), containing BF3·Et2O in CH2Cl2 to give the biaryl coupling products 4a–e, 5a–c and 6a–e in good yields.

  苯酚醚衍生物（非酚类衍生物）、1,3-二元丙烷 1a-e、N-苄基-N-苯乙胺 2a-c 和 N,N-二苄胺 3a-e 在 CH2Cl2 中与含有 BF3-Et2O 的高价碘试剂苯基碘（III）双（三氟乙酸盐）（PIFA）发生反应，以良好的收率得到双芳基偶联产物 4a-e、5a-c 和 6a-e。
• Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent
  作者：Takeshi Takada、Mitsuhiro Arisawa、Michiyo Gyoten、Ryuji Hamada、Hirofumi Tohma、Yasuyuki Kita

  DOI：10.1021/jo980704f

  日期：1998.10.1

  The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a-e), N-benzyl-N-phenethylamines (2a-c) and N,N-dibenzylamines (3a-e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3. Et2O in CH2Cl2 to give the biaryl coupling products (4-6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12-15), whose side chain moiety could be easily cleaved by the known method to give 2,2'-substituted biphenyl compounds (16-18).
• An Oxidative Intramolecular Phenolic Coupling Reaction for the Synthesis of Amaryllidaceae Alkaloids Using a Hypervalent Iodine(III) Reagent
  作者：Yasuyuki Kita、Takeshi Takada、Michiyo Gyoten、Hirofumi Tohma、Meinhart H. Zenk、Jörg Eichhorn

  DOI：10.1021/jo9606766

  日期：1996.1.1

  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.
• A General Electro‐Synthesis Approach to Amaryllidaceae Alkaloids
  作者：Dennis Pollok、Luca M. Großmann、Torsten Behrendt、Till Opatz、Siegfried R. Waldvogel

  DOI：10.1002/chem.202201523

  日期：2022.9.6

  Highly pharmaceutically relevant Amaryllidaceae alkaloids have been accessed by a versatile electro-organic key transformation, including a precursor of the acetylcholinesterase inhibitor galantamine, used as FDA-approved drug for the treatment of Alzheimer's disease. Spirodienone-type intermediates were obtained in a regioselective and sustainable anodic key transformation from nature-derived starting

  高度药学相关的石蒜科生物碱已通过多功能电有机关键转化获得，其中包括乙酰胆碱酯酶抑制剂加兰他敏的前体，该药物被 FDA 批准用作治疗阿尔茨海默病的药物。螺二烯酮型中间体是通过区域选择性和可持续的阳极关键转化从天然原料中获得的