(2S)-1-Isopropylamino-3-phenoxy-2-propanol | 106351-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-1-Isopropylamino-3-phenoxy-2-propanol
• 英文别名: (S)-1-isopropylamino-3-phenoxypropan-2-ol；(-)-(2S)-1-((1-Methylethyl)amino)-3-phenoxy-2-propanol；(2S)-1-phenoxy-3-(propan-2-ylamino)propan-2-ol
• CAS: 106351-44-4
• 化学式: C₁₂H₁₉NO₂
• mdl: MFCD00458477
• 分子量: 209.288
• InChiKey: ONXLHKFGTDDVLQ-NSHDSACASA-N

物化性质

• 沸点：
  341.8±27.0 °C(Predicted)
• 密度：
  1.030±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：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-1-Isopropylamino-3-phenoxy-2-propanol 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (RS)-1-(N-benzyl)isopropylamino-3-phenoxyprop-2-yl 2-fluorophenylacetate
  参考文献：
  名称：

  Determination of the enantiomeric purity and the configuration of β-aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to β-blockers

  摘要：

  A method has been developed for determining the enantiomeric purity and the absolute configuration of beta-aminoalcohols of type ArOCH2CH(OH)CH2NHR (R = iPr, tBu). To determine enantiomeric purity, the amine function was first protected by a benzyl group, then the compound formed was esterified using the acid chloride of (R)-2-fluorophenylacetic acid (AFPA). The F-19 NMR analysis of the derivative obtained revealed the presence of two distinctly separate signals (similar to 2.5 ppm), the one for the RS-SR pair being the most deshielded. The configuration was determined directly on the aminoalcohol by using the acid. In stoichiometric conditions, when R = iPr, the amide function was obtained very preponderantly. The F-19 NMR spectrum of the amide presented four distinct signals when derivatization was carried out by means of a reaction between the (+/-)-beta-aminoalcohol and the (R)-AFPA. The extreme signals, which were over 3.5 ppm apart, did not belong to the same diastereomer. With R = tBu essentially the ester function was obtained. The first studies revealed the presence of two signals, though not as clearly separated as in the previous cases. Each experiment was simple to perform, and purification was not necessary. Mosher's acid gave unsatisfactory results in each case. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00254-8
• 作为产物：
  描述：

  (R)-1-氯-3-苯氧基异丙醇 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2S)-1-Isopropylamino-3-phenoxy-2-propanol
  参考文献：
  名称：

  Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers II. Building blocks of high optical purity and their synthetic conversion

  摘要：

  Based on previous screening results a series of potential building blocks 2-4 for beta-adrenergic blockers were prepared both by enzymatic hydrolysis and acyltransfer and further transformed into the corresponding oxiranes and aminoalcohols of defined absolute configurations.

  DOI：

  10.1016/s0957-4166(00)80191-3

文献信息

• Dynamic kinetic asymmetric synthesis of β-aminoalcohols from racemic epoxides in cyclodextrin complexes under solid state conditions
  作者：L. Rajender Reddy、N. Bhanumathi、K. Rama Rao

  DOI：10.1039/b004643o

  日期：——

  It has been shown for the first time that enantiopure β-aminoalcohols can be prepared from racemic epoxides by dynamic kinetic resolution involving enantio-differentiating racemisation in cyclodextrin complexes under solid state conditions.

  研究首次证明，在固态条件下，通过环糊精络合物中的对映体分化消旋化动态动力学解析，可从外消旋环氧化物制备出对映体纯δ-氨基丙醇。
• Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: an efficient route to 1,2-azido alcohols
  作者：Ahmed Kamal、M Arifuddin、Maddamsetty V Rao

  DOI：10.1016/s0957-4166(99)00464-4

  日期：1999.11

  The ring opening of epoxides with nucleophiles such as TMSN3 and isopropylamine takes place enantioselectively in the presence of (beta-cyclodextrin under extremely mild conditions and the azido alcohols and amino alcohols are formed as (S)-isomers. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Villa; Villa; Pallavicini, Il Farmaco, 1995, vol. 50, # 10, p. 643 - 658
  作者：Villa、Villa、Pallavicini、Romeo、Valoti、Ferri、Iuliano、Brunello

  DOI：——

  日期：——
• Enzyme catalyzed stereoselective synthesis of (S)-propanolamines
  作者：Ahmed Kamal、Maddamsetty V Rao

  DOI：10.1016/s0957-4166(00)86256-4

  日期：1994.10

  Stereoselective synthesis of (S)-propanolamines has been carried out by the ring opening of racemic epoxides with 2-propylamine in presence of lipases and subtilisin. The effect of solvent towards selectivity has also been studied.
• Stereoselective synthesis of (S)-propanol amines: Lipase catalyzed opening of epoxides with 2-propylamine
  作者：Ahmed Kamal、Yalamati Damayanthi、Maddamsetty V. Rao

  DOI：10.1016/0957-4166(92)80006-i

  日期：1992.11

  The ring opening of epoxides with 2-propylamine in presence of lipase in organic solvents affords selectively (S)-propanol amines. The effect of solvents towards selectivity has also been examined.