(Alpha-氨基乙基)(2,5-二甲氧基苯基)酮 | 103565-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (Alpha-氨基乙基)(2,5-二甲氧基苯基)酮
• 中文别名: 2-氨基-1-(2,5-二甲氧基苯基)-1-丙酮；(Α-氨基乙基)(2,5-二甲氧基苯基)酮
• 英文名称: 2,5-dimethoxy-α-aminopropiophenone hydrochloride
• 英文别名: 2-amino-1-(2,5-dimethoxyphenyl)propan-1-one hydrochloride；2-Amino-1-(2,5-dimethoxy-phenyl)-propan-1-on; Hydrochlorid；2-Amino-1-(2,5-dimethoxyphenyl)-1-propanone hydrochloride；2-amino-1-(2,5-dimethoxyphenyl)propan-1-one;hydrochloride
• CAS: 103565-48-6
• 化学式: C₁₁H₁₅NO₃*ClH
• 分子量: 245.706
• InChiKey: SNZUJCDRFAWDRT-UHFFFAOYSA-N

物化性质

• 熔点：
  176 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

化学性质： 这是一种浅黄色结晶物质，熔点高于170℃（在此温度下开始分解）。

用途： 它是甲氧胺的中间体。

生产方法： 首先，使用对苯二酚与硫酸二甲酯在碱性条件下进行甲基化反应，生成二甲氧基苯。随后，在三氯化铝的催化作用下，将二甲氧基苯与丙酰氯缩合得到2,5-二甲氧基苯丙酮。接着，在氯化氢的作用下，使2,5-二甲氧基苯丙酮与甲酯亚硝酸盐发生缩合反应生成α-(N-羟基亚氨基)-2,5-二甲氧基苯丙酮。最后，在钯炭催化剂的催化作用下进行氢化反应，制得所需产品。

反应信息

• 作为反应物：
  描述：

  (Alpha-氨基乙基)(2,5-二甲氧基苯基)酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 2-amino-1-(2,5-dimethoxyphenyl)-1-propanol
  参考文献：
  名称：

  MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position

  摘要：

  Twenty-nine arylisopropylamines, substituted at the beta-position of their side chain by an oxo, hydroxy, or methoxy group, were evaluated in vitro as MAO-A and MAO-B inhibitors. The oxo derivatives ('cathinones') were in general less active as MAO-A inhibitors than the corresponding arylisopropylamines, but exhibited an interesting MAO-13 inhibiting activity, which was absent in the hydroxy, methoxy, and beta-unsubstituted analogues. These results suggest that selective affinity for the two MAO isoforms in this family of compounds is modulated not only by the aryl substitution pattern but also by the side-chain substituents on the aryl-alkylamine scaffold. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.033
• 作为产物：
  描述：

  (RS)-2-三氟乙酰氨基-1-(2,5-二甲氧基苯基)-1-丙酮 在 盐酸 作用下， 以 异丙醇 为溶剂， 以75%的产率得到(Alpha-氨基乙基)(2,5-二甲氧基苯基)酮
  参考文献：
  名称：

  MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position

  摘要：

  Twenty-nine arylisopropylamines, substituted at the beta-position of their side chain by an oxo, hydroxy, or methoxy group, were evaluated in vitro as MAO-A and MAO-B inhibitors. The oxo derivatives ('cathinones') were in general less active as MAO-A inhibitors than the corresponding arylisopropylamines, but exhibited an interesting MAO-13 inhibiting activity, which was absent in the hydroxy, methoxy, and beta-unsubstituted analogues. These results suggest that selective affinity for the two MAO isoforms in this family of compounds is modulated not only by the aryl substitution pattern but also by the side-chain substituents on the aryl-alkylamine scaffold. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.033

文献信息

• 一种盐酸甲氧明聚合物杂质及其制备方法
  申请人：广东嘉博制药有限公司

  公开号：CN113429354A

  公开（公告）日：2021-09-24

  本发明公开了一种盐酸甲氧明聚合物杂质及其制备方法，属于药物化学合成技术领域。本发明盐酸甲氧明聚合物杂质的制备方法为：以1‑(2，5‑二甲氧基苯基)‑2‑氨基‑1‑丙酮为原料，在酸性条件下成环得到盐酸甲氧明聚合物杂质；或以2，3‑二甲基‑1，4‑丁二酸、2，3‑二甲基‑1，4‑丁二酰氯、2，3‑二甲基丁二酸酐中的一种、苯二甲醚为原料，经傅克反应得到盐酸甲氧明聚合物杂质。本发明制备的盐酸甲氧明聚合物杂质的反应条件温和、工艺过程简单。
• 一种赤式结构盐酸甲氧明的制备方法
  申请人：广东嘉博制药有限公司

  公开号：CN103755578B

  公开（公告）日：2016-07-06

  本发明公开了一种赤式结构盐酸甲氧明的制备方法，该方法包括以下步骤：（1）将初始原料2，5-二甲基苯丙酮溶于有机溶剂中，在通入干燥氯化氢气体的条件下，滴加亚硝酸正丁酯溶液进行肟化反应，得到中间体I；（2）在酸性条件下，以甲醇溶液作为溶剂，以钯碳作为催化剂，采用氢气使中间体I中的肟基还原，得到中间体II；（3）中间体II进行氢化还原反应，得到赤式结构盐酸甲氧明。本发明方法的操作简单，经济环保，反应条件温和，同时产品质量优良，产率高，能得到单独的赤式结构盐酸甲氧明。
• CN116574018
  申请人：——

  公开号：——

  公开（公告）日：——
• MAO inhibition by arylisopropylamines: the effect of oxygen substituents at the β-position
  作者：Mauricio Osorio-Olivares、Marcos Caroli Rezende、Silvia Sepúlveda-Boza、Bruce K Cassels、Angélica Fierro

  DOI：10.1016/j.bmc.2004.05.033

  日期：2004.8.1

  Twenty-nine arylisopropylamines, substituted at the beta-position of their side chain by an oxo, hydroxy, or methoxy group, were evaluated in vitro as MAO-A and MAO-B inhibitors. The oxo derivatives ('cathinones') were in general less active as MAO-A inhibitors than the corresponding arylisopropylamines, but exhibited an interesting MAO-13 inhibiting activity, which was absent in the hydroxy, methoxy, and beta-unsubstituted analogues. These results suggest that selective affinity for the two MAO isoforms in this family of compounds is modulated not only by the aryl substitution pattern but also by the side-chain substituents on the aryl-alkylamine scaffold. (C) 2004 Elsevier Ltd. All rights reserved.