(1S,2R)-2-((5-ethylthiophen-2-yl)methyleneamino)-1-phenylpropan-1-ol | 1431846-76-2

• 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: (1S,2R)-2-((5-ethylthiophen-2-yl)methyleneamino)-1-phenylpropan-1-ol
• 英文别名: (1S,2R)-2-[(5-ethylthiophen-2-yl)methylideneamino]-1-phenylpropan-1-ol
• CAS: 1431846-76-2
• 化学式: C₁₆H₁₉NOS
• 分子量: 273.399
• InChiKey: CQSYKVPMEZVBFY-MLGOLLRUSA-N

物化性质

• 沸点：
  420.0±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-((5-ethylthiophen-2-yl)methyleneamino)-1-phenylpropan-1-ol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 (1S,2R)-2-(5-ethylthiophen-2-yl)methylamino-1-phenylpropanol
  参考文献：
  名称：

  新型基于噻吩的手性配体的合成及其在不对称亨利反应中的应用

  摘要：

  由去氧麻黄碱和噻吩甲醛（甲基或乙基取代）合成了新型手性硫醇化氨基醇，并将其用于各种醛与硝基甲烷的催化不对称亨利反应，以高转化率（92％）提供β-羟基硝基链烷醇。根据金属，溶剂，温度和手性配体的量对反应进行了优化。相应的以Cu（OTf）2和2-丙醇为溶剂的催化剂提供了相应的硝基醇对脂肪族醛的最佳对映选择性（最高96％ee）。版权所有©2013 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.2969
• 作为产物：
  描述：

  2-乙基噻吩 在 三氯氧磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.5h， 生成 (1S,2R)-2-((5-ethylthiophen-2-yl)methyleneamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  新型基于噻吩的手性配体的合成及其在不对称亨利反应中的应用

  摘要：

  由去氧麻黄碱和噻吩甲醛（甲基或乙基取代）合成了新型手性硫醇化氨基醇，并将其用于各种醛与硝基甲烷的催化不对称亨利反应，以高转化率（92％）提供β-羟基硝基链烷醇。根据金属，溶剂，温度和手性配体的量对反应进行了优化。相应的以Cu（OTf）2和2-丙醇为溶剂的催化剂提供了相应的硝基醇对脂肪族醛的最佳对映选择性（最高96％ee）。版权所有©2013 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.2969
• 作为试剂：
  描述：

  茴香硫醚 在 bis(acetylacetonate)oxovanadium 、 (1S,2R)-2-((5-ethylthiophen-2-yl)methyleneamino)-1-phenylpropan-1-ol 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.5h， 以90%的产率得到甲基苯基亚砜
  参考文献：
  名称：

  Synthesis of novel β-amino alcohols and their application in the catalytic asymmetric sulfoxidation of sulfides

  摘要：

  Novel chiral norephedrine-based beta-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)(2) for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.011

文献信息

• Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Using Novel Thiophene-Based Chiral Ligands
  作者：A. E. Aydin

  DOI：10.1134/s1070428020050255

  日期：2020.5

  AbstractChiral norephedrine-derived β-amino alcohols with a thiophene moiety were synthesized from thiophene carbaldehydes (methyl- or ethyl-substituted) and chiral amino alcohols, such as both enantiomers of norephedrine and 2-aminopropanol. The synthesized ligands were applied to the catalytic asymmetric addition of diethylzinc to aldehydes to obtain optically active alcohols with a high conversion (92%)

  摘要由噻吩甲醛（甲基或乙基取代的）和手性氨基醇（如去氧麻黄碱和2-氨基丙醇的对映异构体）合成具有噻吩部分的手性去氧麻黄碱衍生的β-氨基醇。将合成的配体用于将二乙基锌催化不对称加成到醛中，从而获得具有高转化率（92％）和出色的对映选择性（ee高达99％）的旋光醇。用对-三氟苯甲醛作为含有强电子受体CF 3基团的底物可获得最高的对映选择性（ee 99％）。
• Enantioselective Aldol Reaction between Isatins and Ketones, Catalyzed by Chiral Norephedrine-Derived β-Amino Alcohols with a Thiophene Moiety
  作者：A. E. Aydin

  DOI：10.1134/s1070428022060100

  日期：2022.6
• Synthesis of novel thiophene-based chiral ligands and their application in asymmetric Henry reaction
  作者：A. Ebru Aydin

  DOI：10.1002/aoc.2969

  日期：2013.5

  Novel chiral thiolated amino alcohols were synthesized from norephedrine and thiophene carbaldehydes (methyl‐ or ethyl‐substituted) and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide β‐hydroxy nitroalkanols in high conversion (92%). The reaction was optimized in terms of the metal, solvent, temperature and amount of chiral ligand. The corresponding

  由去氧麻黄碱和噻吩甲醛（甲基或乙基取代）合成了新型手性硫醇化氨基醇，并将其用于各种醛与硝基甲烷的催化不对称亨利反应，以高转化率（92％）提供β-羟基硝基链烷醇。根据金属，溶剂，温度和手性配体的量对反应进行了优化。相应的以Cu（OTf）2和2-丙醇为溶剂的催化剂提供了相应的硝基醇对脂肪族醛的最佳对映选择性（最高96％ee）。版权所有©2013 John Wiley＆Sons，Ltd.
• Synthesis of novel β-amino alcohols and their application in the catalytic asymmetric sulfoxidation of sulfides
  作者：A. Ebru Aydin

  DOI：10.1016/j.tetasy.2013.03.011

  日期：2013.4

  Novel chiral norephedrine-based beta-amino alcohol ligands containing a thiophene ring were prepared from norephedrine and substituted furan carbaldehydes (methyl- or ethyl-substituted) and used in combination with VO(acac)(2) for the asymmetric oxidation of aryl methyl sulfides using H2O2 as an oxidant. Amino alcohol derived Schiff bases 4,5a-b gave higher enantiomeric excesses than amino alcohol-derived reduced Schiff based ligands 6,7a-b. Of these chiral ligands, (1S,2R)-5b and (1S,2R)-7b gave high yields (90%) with moderate to high enantioselectivities (78%, 96% ee, respectively). The oxidation of other aryl methyl sulfides with (1S,2R)-5b and (1S,2R)-7b as ligands afforded the corresponding sulfoxides in 60-89% yields and with 92-99% ee. (C) 2013 Elsevier Ltd. All rights reserved.