(S)-1-isopropylamino-3-(naphthalen-2-yloxy)propan-2-ol | 143487-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-isopropylamino-3-(naphthalen-2-yloxy)propan-2-ol
• 英文别名: (S)-(-)-propranolol；(-)-Propranolol；(S)-propranolol；(2S)-1-naphthalen-2-yloxy-3-(propan-2-ylamino)propan-2-ol
• CAS: 143487-96-1
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: PIANUSMCKHEMFQ-HNNXBMFYSA-N

物化性质

• 熔点：
  82.0-83.7 °C
• 沸点：
  434.9±30.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (S)-1-isopropylamino-3-(naphthalen-2-yloxy)propan-2-ol 生成 (2R)-1-(cyclopentylamino)-3-naphthalen-2-yloxypropan-2-ol
  参考文献：
  名称：

  LAGANIERE, S.;KWONG, E.;SHEN, D. D., J. CHROMATOGR. BIOMED. APPL., 488,(1989) N, C. 407-416

  摘要：

  DOI：
• 作为产物：
  描述：

  1-chloro-3-(naphthalen-2-yloxy)propan-2-ol 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 13.0h， 生成 (S)-1-isopropylamino-3-(naphthalen-2-yloxy)propan-2-ol
  参考文献：
  名称：

  酶辅助制备对映体纯的β-肾上腺素能阻滞剂III。旋光氯醇衍生物及其转化

  摘要：

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。

  DOI：

  10.1016/s0957-4166(00)80256-6

文献信息

• New propranolol analogues: binding and chiral discrimination by cellobiohydrolase Cel7A
  作者：Alexandra Fagerström、Mikael Nilsson、Ulf Berg、Roland Isaksson

  DOI：10.1039/b605603b

  日期：——

  Novel propranolol analogues have been designed and synthesised and their enantioselective binding to the cellulose degrading enzyme, Cel7A, has been evaluated. Affinity and enantioselectivity have been determined by capillary electrophoresis experiments. Ligands with significantly improved affinity and selectivity have been obtained and an analysis of the results has led to insights concerning the relation between the changes in ligand structure and selectivity as well as affinity to the protein.

  新型普萘洛尔类似物被设计和合成，并评估了它们与纤维素降解酶Cel7A的手性选择性结合。通过毛细管电泳实验确定了亲和性和手性选择性。获得了亲和性和选择性显著提高的配体，对结果的分析揭示了配体结构变化与对蛋白质的选择性和亲和性之间的关系。
• Solvent-free aminolysis of aliphatic and aryloxy epoxides with sulfated zirconia as solid acid catalyst
  作者：Arpan K. Shah、Manish Kumar、Sayed H.R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1016/j.apcata.2014.08.024

  日期：2014.9

  Single-step and two-steps synthetic procedure for the synthesis of sulfated zirconia (SZ) was developed, which were calcined at 500, 600 and 700 degrees C and characterized by various physico-chemical methods such as PXRD, FTIR, surface area, microanalysis, NH3-TPD and DRIFT analysis. These SZ materials were then employed as solid acid catalysts for the aminolysis of different aliphatic/aromatic terminal, aryloxy and meso epoxides with aromatic and aliphatic amines under ambient conditions. Amongst the catalyst prepared, SZ-2-600 prepared in two-steps and 600 degrees C calcined was found to be the most efficient catalyst to give beta-amino alcohols in up to 98% yield and >99% regioselectivity. The SZ catalyst was successfully recycled and reused up to six catalytic runs with intact efficiency. (C) 2014 Elsevier B.V. All rights reserved.
• Fe(OH)3 nano solid material: An efficient catalyst for regioselective ring opening of aryloxy epoxide with amines under solvent free condition
  作者：Arpan K. Shah、K. Jeya Prathap、Manish Kumar、Sayed H.R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Hari C. Bajaj

  DOI：10.1016/j.apcata.2013.10.003

  日期：2014.1

  Iron hydroxide-Fe(OH)(3) and iron oxides (Fe3O4 and Fe2O3) were successfully prepared and characterized. These materials were employed as efficient and environmentally benign heterogeneous catalysts for the epoxide ring opening reaction of various alyloxy, terminal and meso epoxides with aromatic and aliphatic amines under solvent free condition at room temperature. Out of these, nano-sized Fe(OH)(3) (IH-1) showed better catalytic activity to give the product beta-amino alcohols in excellent yield (up to similar to 96%) and high regioselectivity in 10-360 min. The catalyst was successfully recycled and reused eight times with no loss in catalytic activity. (C) 2013 Published by Elsevier B.V.
• Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers III. Optically active chlorohydrin derivatives and their conversion
  作者：Ulrich Ader、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)80256-6

  日期：1992.4

  Optical active chlorohydrin derivatives 2a-m and 3a-m of both enantiomeric series were prepared via both enzymatic hydrolyses and acyltransfer reactions catalysed by a highly selective lipase from Pseudomonas sp.. The resulting building blocks were further transformed into the corresponding β-blockers of high enantiomeric purity.

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。
• LAGANIERE, S.;KWONG, E.;SHEN, D. D., J. CHROMATOGR. BIOMED. APPL., 488,(1989) N, C. 407-416
  作者：LAGANIERE, S.、KWONG, E.、SHEN, D. D.

  DOI：——

  日期：——