(2S)-2-(diethylaminomethyl)-1,4-benzodioxane | 687974-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (2S)-2-(diethylaminomethyl)-1,4-benzodioxane
• 英文别名: (2R)-2-diethylaminomethyl-1,4-benzodioxane；(R)-prosympal；(2R)-Prosympal；N-[[(3R)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]-N-ethylethanamine
• CAS: 687974-13-6
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: BGWGNDUTMDMIKZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-苯并二氧六环-2-甲酸乙酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 氯仿 、 正丁醇 为溶剂， 反应 12.0h， 生成 (2S)-2-(diethylaminomethyl)-1,4-benzodioxane
  参考文献：
  名称：

  Chemoenzymatic synthesis of piperoxan, prosympal, dibozane, and doxazosin

  摘要：

  The synthesis of both enantiomers of 1,4-benzodioxan-2-carboxylic acid 1, a key synthetic intermediate for the therapeutic agents piperoxan, prosympal, dibozane, and doxazosin was achieved with good yields and high enantioselectivities via the Arthrobacter sp. lipase catalyzed kinetic resolution of ester (+/-)-17a. The influence of the co-solvents and the immobilization of the lipase upon kinetic resolution demonstrated that immobilized whole cells, in the presence of n-butanol as a co-solvent, resulted in the optimal resolution of the substrate (ee similar to 99%, E = 535) at 258 mmol (50 g/L) substrate concentration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.10.018

文献信息

• A facile approach to chiral 1,4-benzodioxane toward the syntheses of doxazosin, prosympal, piperoxan, and dibozane
  作者：Abdul Rouf、Mushtaq A. Aga、Brijesh Kumar、Subhash Chandra Taneja

  DOI：10.1016/j.tetlet.2013.09.040

  日期：2013.11

  The process describes the concise synthesis of (R/S)-enantiomers of doxazosin, an antidepressant drug and alpha-adrenergic receptor antagonists like prosympal, piperoxan, and dibozane in practical yields from easily available (R)-2,3-O-cyclohexylidene-D-glyceraldehyde and (S)-3-(benzyloxy)propane-1,2-diol. (C) 2013 Elsevier Ltd. All rights reserved.
• Trefouel et al., Bulletin des Sciences Pharmacologiques, 1935, vol. 42, p. 459,462
  作者：Trefouel et al.

  DOI：——

  日期：——
• Chemoenzymatic synthesis of piperoxan, prosympal, dibozane, and doxazosin
  作者：Abdul Rouf、Pankaj Gupta、Mushtaq A. Aga、Brijesh Kumar、Asha Chaubey、Rajinder Parshad、Subhash C. Taneja

  DOI：10.1016/j.tetasy.2012.10.018

  日期：2012.12

  The synthesis of both enantiomers of 1,4-benzodioxan-2-carboxylic acid 1, a key synthetic intermediate for the therapeutic agents piperoxan, prosympal, dibozane, and doxazosin was achieved with good yields and high enantioselectivities via the Arthrobacter sp. lipase catalyzed kinetic resolution of ester (+/-)-17a. The influence of the co-solvents and the immobilization of the lipase upon kinetic resolution demonstrated that immobilized whole cells, in the presence of n-butanol as a co-solvent, resulted in the optimal resolution of the substrate (ee similar to 99%, E = 535) at 258 mmol (50 g/L) substrate concentration. (C) 2012 Elsevier Ltd. All rights reserved.