(2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methylpropylamine | 77066-41-2

• 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: (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methylpropylamine
• 英文别名: (S)-2-N-methyl-(3,4-dimethoxyphenyl)propan-1-amine；(2S)-2-(3,4-dimethoxyphenyl)-N-methylpropan-1-amine
• CAS: 77066-41-2
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: SRQWASKTEGPBJR-SECBINFHSA-N

物化性质

• 沸点：
  292.6±35.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methylpropylamine 在 盐酸 作用下， 反应 16.0h， 以96%的产率得到(4S)-(+)-6,7-dimethoxy-N,4-dimethyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenyl-glycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00343-8
• 作为产物：
  描述：

  在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 6.5h， 生成 (2S)-(-)-2-(3,4-dimethoxyphenyl)-N-methylpropylamine
  参考文献：
  名称：

  Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines

  摘要：

  A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenyl-glycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00343-8

文献信息

• [EN] ISOFORM-SELECTIVE HCN BLOCKERS<br/>[FR] BLOQUEURS SÉLECTIFS D'ISOFORMES DE HCN
  申请人：UNIV FIRENZE

  公开号：WO2011000915A1

  公开（公告）日：2011-01-06

  The present invention relates to compounds of formula (I) as isoform-selective HCN blockers. In particular said compounds showed diverse capabilities of blocking selectively isoforms HCN1, HCN2 and HCN4 expressed in HEK cells. The invention further relates to the medical use of said compounds or as pharmacological or drug-development tools.

  本发明涉及式（I）化合物作为异构体选择性HCN通道阻滞剂。特别是这些化合物显示出在HEK细胞中选择性阻断HCN1、HCN2和HCN4异构体的多样能力。本发明还涉及将这些化合物用于医学用途或作为药理学或药物开发工具。
• Design, Synthesis, and Preliminary Biological Evaluation of New Isoform-Selective f-Current Blockers
  作者：Michele Melchiorre、Martina Del Lungo、Luca Guandalini、Elisabetta Martini、Silvia Dei、Dina Manetti、Serena Scapecchi、Elisabetta Teodori、Laura Sartiani、Alessandro Mugelli、Elisabetta Cerbai、Maria Novella Romanelli

  DOI：10.1021/jm1006758

  日期：2010.9.23

  New I-f blockers have been designed and tested on HEK293 cells stably expressing the HCN1, HCN2, and HCN4 channels to find compounds able to discriminate among the channel isoforms. Among the synthesized compounds, the cis-butene derivative (R)-5 shows some preference for HCN2 while the pseudodimeric product (R)-6 shows selectivity for HCN1. These compounds can be important pharmacological tools to study the channels in native tissues and may be useful to design safe drugs.
• Stereocontrolled metalloenamine alkylations: application to the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines
  作者：Jose L Vicario、Dolores Badı́a、Esther Domı́nguez、Luisa Carrillo

  DOI：10.1016/s0957-4166(00)00343-8

  日期：2000.9

  A procedure for the asymmetric synthesis of 4-alkyl-1,2,3,4-tetrahydroisoquinolines is described. The key step in the synthetic route is a stereocontrolled metalloenamine alkylation using (R)-(+)-phenyl-glycinol methyl ether as the chiral auxiliary. Subsequent N-methylation, hydrogenolysis and cyclization afforded the target heterocycles with enantiomeric excesses higher than 99%. (C) 2000 Elsevier Science Ltd. All rights reserved.