((3,5-dimethoxy-4-hydroxyphenyl)acetyl)pyrrolidine | 131656-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ((3,5-dimethoxy-4-hydroxyphenyl)acetyl)pyrrolidine
• 英文别名: 2-(4-hydroxy-3,5-dimethoxyphenyl)-1-pyrrolidin-1-ylethanone
• CAS: 131656-84-3
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: JSSQTYZIKHFOSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((3,5-dimethoxy-4-hydroxyphenyl)acetyl)pyrrolidine 在 4-二甲氨基吡啶 、 四乙基对甲苯磺酸铵 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-methoxy-N-((3,5-dimethoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine
  参考文献：
  名称：

  Anodic amide oxidations in the presence of electron-rich phenyl rings: evidence for an intramolecular electron-transfer mechanism

  摘要：

  The anodic oxidations of amides in the presence of mono-, di-, and trialkoxyphenyl rings were examined. Although literature reduction potentials suggest that these oxidations would lead to either selective aromatic ring oxidation or mixtures, the chemoselectivity of the reactions was found to be dependent on the substitution pattern of the phenyl ring. For example, the anodic oxidations of ((3-methoxyphenyl)acetyl)pyrrolidine, ((2-methoxyphenyl)acetyl)pyrrolidine, ((3-methoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine, and ((3,5-dimethoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine all led to selective methoxylation of the pyrrolidine ring. The anodic oxidations of ((4-methoxyphenyl)acetyl)pyrrolidine and ((3,4-methoxyphenyl)acetyl)pyrrolidine led to selective methoxylation of the benzylic carbon. Mechanistic studies indicate that both amide and aryl oxidation processes compete under the reaction conditions, but that intramolecular electron transfer leads to the selective formation of products. Evidence for this mechanism was obtained by examining the cyclic voltammogram of ((3-methoxyphenyl)-acetyl)pyrrolidine, competition studies, and the preparative electrolysis of ((4-methoxyphenyl)dimethyl-acetyl)pyrrolidine. The methoxylated amides were cyclized to form tricyclic amides using titanium tetrachloride.

  DOI：

  10.1021/jo00003a029
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙酸 在 草酰氯 、 碘代三甲硅烷 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 ((3,5-dimethoxy-4-hydroxyphenyl)acetyl)pyrrolidine
  参考文献：
  名称：

  Anodic amide oxidations in the presence of electron-rich phenyl rings: evidence for an intramolecular electron-transfer mechanism

  摘要：

  The anodic oxidations of amides in the presence of mono-, di-, and trialkoxyphenyl rings were examined. Although literature reduction potentials suggest that these oxidations would lead to either selective aromatic ring oxidation or mixtures, the chemoselectivity of the reactions was found to be dependent on the substitution pattern of the phenyl ring. For example, the anodic oxidations of ((3-methoxyphenyl)acetyl)pyrrolidine, ((2-methoxyphenyl)acetyl)pyrrolidine, ((3-methoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine, and ((3,5-dimethoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine all led to selective methoxylation of the pyrrolidine ring. The anodic oxidations of ((4-methoxyphenyl)acetyl)pyrrolidine and ((3,4-methoxyphenyl)acetyl)pyrrolidine led to selective methoxylation of the benzylic carbon. Mechanistic studies indicate that both amide and aryl oxidation processes compete under the reaction conditions, but that intramolecular electron transfer leads to the selective formation of products. Evidence for this mechanism was obtained by examining the cyclic voltammogram of ((3-methoxyphenyl)-acetyl)pyrrolidine, competition studies, and the preparative electrolysis of ((4-methoxyphenyl)dimethyl-acetyl)pyrrolidine. The methoxylated amides were cyclized to form tricyclic amides using titanium tetrachloride.

  DOI：

  10.1021/jo00003a029

文献信息

• MOELLER, KEVIN D.;WANG, PO W.;TARAZI, SHARIF;MARZABADI, MOHAMMAD R.;WONG,+, J. ORG. CHEM., 56,(1991) N, C. 1058-1067
  作者：MOELLER, KEVIN D.、WANG, PO W.、TARAZI, SHARIF、MARZABADI, MOHAMMAD R.、WONG,+

  DOI：——

  日期：——
• [EN] GLYCOSYLATED MESCALINE DERIVATIVES AND METHODS OF USING<br/>[FR] DÉRIVÉS DE MÉCALINE GLYCOSYLÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：[en]ENVERIC BIOSCIENCES CANADA INC.

  公开号：WO2023102658A1

  公开（公告）日：2023-06-15

  Disclosed are novel glycosylated mescaline derivative compounds that exhibit selective binding to the HT1A receptor over HT2A receptor and pharmaceutical and recreational drug formulations containing the same. The compounds may be produced by reacting a hydroxylated mescaline derivative with a glycosylating compound. Formulas (IV) & (V).
• WO2023/44574
  申请人：——

  公开号：——

  公开（公告）日：——
• Anodic amide oxidations in the presence of electron-rich phenyl rings: evidence for an intramolecular electron-transfer mechanism
  作者：Kevin D. Moeller、Po W. Wang、Sharif Tarazi、Mohammad R. Marzabadi、Poh Lee Wong

  DOI：10.1021/jo00003a029

  日期：1991.2

  The anodic oxidations of amides in the presence of mono-, di-, and trialkoxyphenyl rings were examined. Although literature reduction potentials suggest that these oxidations would lead to either selective aromatic ring oxidation or mixtures, the chemoselectivity of the reactions was found to be dependent on the substitution pattern of the phenyl ring. For example, the anodic oxidations of ((3-methoxyphenyl)acetyl)pyrrolidine, ((2-methoxyphenyl)acetyl)pyrrolidine, ((3-methoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine, and ((3,5-dimethoxy-4-(pivaloyloxy)phenyl)acetyl)pyrrolidine all led to selective methoxylation of the pyrrolidine ring. The anodic oxidations of ((4-methoxyphenyl)acetyl)pyrrolidine and ((3,4-methoxyphenyl)acetyl)pyrrolidine led to selective methoxylation of the benzylic carbon. Mechanistic studies indicate that both amide and aryl oxidation processes compete under the reaction conditions, but that intramolecular electron transfer leads to the selective formation of products. Evidence for this mechanism was obtained by examining the cyclic voltammogram of ((3-methoxyphenyl)-acetyl)pyrrolidine, competition studies, and the preparative electrolysis of ((4-methoxyphenyl)dimethyl-acetyl)pyrrolidine. The methoxylated amides were cyclized to form tricyclic amides using titanium tetrachloride.