2-amino-1-(2,5-dimethoxyphenyl)-1-propanol | 715-83-3

• 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: 2-amino-1-(2,5-dimethoxyphenyl)-1-propanol
• 英文别名: (RS)-methoxamine；(1RS:2SR)-2-amino-1-(2.5-dimethoxy-phenyl)-propanol-(1)；(1S,2R)-2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
• CAS: 715-83-3
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: WJAJPNHVVFWKKL-RDDDGLTNSA-N

物化性质

• 沸点：
  368.4±42.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-1-(2,5-dimethoxyphenyl)-1-propanol 、 乙酸酐 生成 (1RS,2SR)-1-acetoxy-2-acetylamino-1-(2,5-dimethoxy-phenyl)-propane
  参考文献：
  名称：

  Characteristics of β-[2,5-Dimethoxyphenyl]-β-hydroxyisopropylamine Hydrochloride

  摘要：

  DOI：

  10.1021/ja01264a501
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 2-amino-1-(2,5-dimethoxyphenyl)-1-propanol
  参考文献：
  名称：

  Satoda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 989,992

  摘要：

  DOI：

文献信息

• Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D-Printed Mesoreactors
  作者：Sergio Rossi、Riccardo Porta、Davide Brenna、Alessandra Puglisi、Maurizio Benaglia

  DOI：10.1002/anie.201612192

  日期：2017.4.3

  to 90 % ee. The method was applied to the continuous‐flow synthesis of biologically active chiral 1,2‐amino alcohols (norephedrine, metaraminol, and methoxamine) through a two‐step sequence combining the nitroaldol reaction with a hydrogenation. To highlight potential industrial applications of this method, a multistep continuous synthesis of norephedrine has been realized. The product was isolated

  设计了3D打印的流动反应器，该反应器由不同的材料（PLA，HIPS，尼龙）制成，并用于催化立体选择性亨利反应。使用易于制备且可调的3D打印反应堆，可以快速筛选具有不同尺寸，形状和通道尺寸的设备，旨在确定性能最佳的反应堆设置。经过优化的工艺可提供高收率，中等非对映选择性和高达90％ee的产物。该方法通过将硝基羟醛反应与加氢反应结合起来的两步法应用于生物活性手性1,2-氨基醇（去氧麻黄碱，间氨基苯胺和甲氧胺）的连续流合成。为了突出该方法的潜在工业应用，已经实现了去甲麻黄碱的多步连续合成。无需任何中间纯化或溶剂切换即可分离出产物。
• Processes for preparing optically active alcohols and optically active amines
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0736509A2

  公开（公告）日：1996-10-09

  A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active β-aminoalcohol and a boron hydride; or obtained from the optically active β-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active β-aminoalcohol and a boron hydride, or obtained from said optically active β-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.

  一种制备光学活性醇的工艺，其方法是将对应于光学活性醇的手性酮和酸与(1)选自以下组别的含硼化合物和(2)选自以下组别的含硼化合物的混合物反应：①从光学活性β-氨基醇和氢化硼中得到的硼烷化合物；或从光学活性β-氨基醇、金属硼氢化物和酸中得到的硼烷化合物；②光学活性噁唑硼烷和(2)金属硼氢化物；以及一种制备光学活性胺的工艺，其方法是使肟衍生物和酸与(1)一种含硼化合物与(2)一种金属硼氢化物的混合物反应，该含硼化合物选自以下组别：(1)一种硼烷化合物，该硼烷化合物由光学活性β-氨基醇和硼氢化物得到，或由所述光学活性β-氨基醇、金属硼氢化物和酸得到；以及(2)一种光学活性噁唑硼烷和(2)一种金属硼氢化物。
• 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.
• XIYAMA, TAMEHDZIRO;FUDZITA, MAKOTO
  作者：XIYAMA, TAMEHDZIRO、FUDZITA, MAKOTO

  DOI：——

  日期：——
• Process for producing (R)-styrene oxides
  申请人：SUMIKA FINE CHEMICAL COMPANY, LTD.

  公开号：EP0735142B1

  公开（公告）日：2001-10-24