(R)-1-methyl-6,7-dimethoxytetrahydroisoquinoline | 1408003-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (R)-1-methyl-6,7-dimethoxytetrahydroisoquinoline
• 英文别名: prop-2-enyl (1R)-6,7-dimethoxy-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1408003-62-2
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: VJVLGFKKLBRXSK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-methyl-6,7-dimethoxytetrahydroisoquinoline 在 三乙醇胺 、 sodium hydroxide 作用下， 反应 6.0h， 生成 鹿尾草定
  参考文献：
  名称：

  Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol

  摘要：

  An efficient chemoenzymatic route for the synthesis of enantiopure (R)-salsolinol through the use of Candida antarctica lipase A (CALA) was developed. Different parameters, including the acyl agent, the solvent, the temperature, and the amount of enzyme and substrates used, were investigated in order to establish the optimal reaction conditions for the enzymatic kinetic resolution of secondary amines. The combination of CALA with phenyl allyl carbonates in toluene allowed the isolation of amines with high conversion (50%) and ee (98%) values.(C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.009
• 作为产物：
  描述：

  碳酸烯丙基苯酯 、 6,7-二甲氧基-1-甲基-1,2,3,4-四氢异喹啉 在 Lipase AY (Candida rugosa) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以39%的产率得到(R)-1-methyl-6,7-dimethoxytetrahydroisoquinoline
  参考文献：
  名称：

  Efficient lipase-catalysed route for the kinetic resolution of salsolidine and its ß-carboline analogue

  摘要：

  Racemic 1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 1 and 1-methyl-1,2,3,4-tetrahydro-ss-carboline 3 were resolved through lipase-catalysed asymmetric acylation on the secondary amino group. High enantioselectivities (E >200) were observed when the acylation of racemic 1 was performed with phenyl ally! carbonate in the presence of Candida rugosa lipase in toluene at 40 degrees C or with Candida antarctica lipase B in tert-butyl methyl ether at 50 degrees C. Excellent enantioselectivity (E >200) characterised the CAL-B-catalysed acylation of racemic 3 with phenyl allyl carbonate in the presence of triethylamine in tert-butyl methyl ether at 50 degrees C. The product (R)-carbamates (ee >97%) were hydrolysed into the corresponding (R)-enantiomers of the free amines 1 and 3 (ee = 99%) with the use of Pd-2(dba)(3).CHCl3 catalyst. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.019

文献信息

• Lipase-catalyzed synthesis of the chiral tetrahydroisoquinoline (R)-salsolinol
  作者：Wei Ding、Mingze Li、Rongji Dai、Yulin Deng

  DOI：10.1016/j.tetasy.2012.09.009

  日期：2012.10

  An efficient chemoenzymatic route for the synthesis of enantiopure (R)-salsolinol through the use of Candida antarctica lipase A (CALA) was developed. Different parameters, including the acyl agent, the solvent, the temperature, and the amount of enzyme and substrates used, were investigated in order to establish the optimal reaction conditions for the enzymatic kinetic resolution of secondary amines. The combination of CALA with phenyl allyl carbonates in toluene allowed the isolation of amines with high conversion (50%) and ee (98%) values.(C) 2012 Elsevier Ltd. All rights reserved.
• Efficient lipase-catalysed route for the kinetic resolution of salsolidine and its ß-carboline analogue
  作者：Barbara Kovács、Rita Megyesi、Enikő Forró、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2017.10.019

  日期：2017.12

  Racemic 1-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 1 and 1-methyl-1,2,3,4-tetrahydro-ss-carboline 3 were resolved through lipase-catalysed asymmetric acylation on the secondary amino group. High enantioselectivities (E >200) were observed when the acylation of racemic 1 was performed with phenyl ally! carbonate in the presence of Candida rugosa lipase in toluene at 40 degrees C or with Candida antarctica lipase B in tert-butyl methyl ether at 50 degrees C. Excellent enantioselectivity (E >200) characterised the CAL-B-catalysed acylation of racemic 3 with phenyl allyl carbonate in the presence of triethylamine in tert-butyl methyl ether at 50 degrees C. The product (R)-carbamates (ee >97%) were hydrolysed into the corresponding (R)-enantiomers of the free amines 1 and 3 (ee = 99%) with the use of Pd-2(dba)(3).CHCl3 catalyst. (C) 2017 Elsevier Ltd. All rights reserved.