(S)-2-(morpholin-1-yl)-1-phenylethanol | 87837-32-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(morpholin-1-yl)-1-phenylethanol
• 英文别名: (S)-2-(morpholin-4-yl)-1-phenylethanol；(S)-2-morpholino-1-phenylethan-1-ol；(+)-S-2-morpholino-1-phenylethanol；2-morpholino-1-phenylethanol；(1S)-2-morpholin-4-yl-1-phenylethanol
• CAS: 87837-32-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: CKCUWHAMJDWXOH-GFCCVEGCSA-N

物化性质

• 沸点：
  342.0±32.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(morpholin-1-yl)-1-phenylethanol 在 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 反应 20.5h， 生成 (S)-N,N-dietyl-1-phenyl-2-(morpholin-4-yl)ethanamine
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 (S)-2-(morpholin-1-yl)-1-phenylethanol
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9
• 作为试剂：
  描述：

  4-morpholinylacetophenone 在 lithium aluminium tetrahydride 、 N-乙基苯胺 、 (S)-2-(morpholin-1-yl)-1-phenylethanol 作用下， 以 乙醚 为溶剂， 生成 (R)-2-morpholino-1-phenylethanol 、 (S)-2-(morpholin-1-yl)-1-phenylethanol
  参考文献：
  名称：

  Asymmetric Self-Replication of Chiral 1,2-Amino Alcohols by Highly Enantioselective Autoinductive Reduction

  摘要：

  DOI：

  10.1002/anie.199724581

文献信息

• Application of Tethered Ruthenium Catalysts to Asymmetric Hydrogenation of Ketones, and the Selective Hydrogenation of Aldehydes
  作者：Katherine E. Jolley、Antonio Zanotti‐Gerosa、Fred Hancock、Alan Dyke、Damian M. Grainger、Jonathan A. Medlock、Hans G. Nedden、Jacques J. M. Le Paih、Stephen J. Roseblade、Andreas Seger、Vilvanathan Sivakumar、Ivan Prokes、David J. Morris、Martin Wills

  DOI：10.1002/adsc.201200362

  日期：2012.9.17

  An improved method for the synthesis of tethered ruthenium(II) complexes of monosulfonylated diamines is described, together with their application to the hydrogenation of ketones and aldehydes. The complexes were applied directly, in their chloride form, to asymmetric ketone hydrogenation, to give products in excess of 99% ee in the best cases, using 30 bar of hydrogen at 60 °C, and to the selective

  描述了一种改进的合成方法，用于合成单磺酰化二胺的束缚钌（II）配合物，以及它们在酮和醛加氢中的应用。将络合物以氯化物形式直接用于不对称酮的氢化反应，在最佳情况下，在60°C的条件下使用30 bar氢气，可提供超过99％ee的产物，并选择性还原醛，而不是其他官能团。组。
• Magnetic Nano Fe3O4 Catalyzed Solvent-Free Stereo- and Regioselective ­Aminolysis of Epoxides by Amines; a Green Method for the Synthesis of β-Amino Alcohols
  作者：Srinivasarao Babu、Amit Kumar、Ramarao Parella

  DOI：10.1055/s-0033-1340844

  日期：——

  We report the use of magnetic nano Fe3O4 as a mild heterogeneous catalyst for the aminolysis of epoxides with amines. The approach constitutes a green method for the formation of a variety of β-amino alcohols with very high stereo- and regioselectivity under solvent-free and ambient reaction conditions. The aminolysis of chiral epoxides with amines gave the corresponding chiral β-amino alcohols with

  我们报告了使用磁性纳米 Fe3O4 作为温和的多相催化剂，用于环氧化物与胺的氨解。该方法构成了一种在无溶剂和环境反应条件下形成具有非常高立体选择性和区域选择性的各种 β-氨基醇的绿色方法。手性环氧化物与胺的氨解得到相应的手性 β-氨基醇，立体化学完全反转。磁性纳米Fe3O4催化剂易于回收和循环利用。
• Green Regio- and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent-Free Conditions
  作者：Maria Rosaria Acocella、Luciana D'Urso、Mario Maggio、Gaetano Guerra

  DOI：10.1002/cctc.201600241

  日期：2016.6.7

  The ring‐opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high‐surface‐area graphite and graphene oxide under metal‐free and solvent‐free conditions. For epoxides without aryl groups, catalytic activity was observed only for graphene oxide, and hence, the activity must have been due to its acidic groups. For styrene oxide, instead, graphite and graphene oxide

  在无金属和无溶剂条件下，高表面积的石墨和氧化石墨烯可有效地和区域选择性地催化环氧化物与胺的开环反应。对于不具有芳基的环氧化物，仅对氧化石墨烯观察到催化活性，因此，该活性必须归因于其酸性基团。相反，对于氧化苯乙烯，石墨和氧化石墨烯表现出相当相似的催化活性，因此，活性主要是由于与石墨π系统的π堆积相互作用而使亲电子环氧化物活化。所描述的氨解过程是绿色且廉价的，因为催化剂可以被回收和再循环而不损失效率。而且，
• Acid-Assisted Ru-Catalyzed Enantioselective Amination of 1,2-Diols through Borrowing Hydrogen
  作者：Li-Cheng Yang、Ya-Nong Wang、Yao Zhang、Yu Zhao

  DOI：10.1021/acscatal.6b02959

  日期：2017.1.6

  Here, we present a highly enantioselective synthesis of 1,2-amino alcohols from readily available racemic 1,2-diols through a borrowing hydrogen process. An intriguing acid effect was discovered for this Ru-catalyzed amination reaction, which led to a significant improvement of the stereoselectivity of the process. Preliminary mechanistic studies suggest a scenario of Brønsted acid-assisted dynamic

  在这里，我们介绍了通过借用氢过程从容易获得的外消旋1,2-二醇中高度对映选择性合成1,2-氨基醇的方法。对于这种Ru催化的胺化反应，发现了一种引人入胜的酸效应，这导致了该方法的立体选择性的显着改善。初步的机理研究表明，布朗斯台德酸辅助的醇动力学动力学不对称胺化的情况。
• Ruthenium-Catalyzed Enantioselective Synthesis of β-Amino Alcohols from 1,2-Diols by “Borrowing Hydrogen”
  作者：Anggi Eka Putra、Yohei Oe、Tetsuo Ohta

  DOI：10.1002/ejoc.201300692

  日期：2013.9

  Enantioselective synthesis of β-amino alcohols from 1,2-diols by the use of [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS catalysis was developed. Several 1,2-diols were treated with secondary amines to afford the corresponding optically active β-amino alcohols in up to 99 % yield with 77 % ee.

  开发了使用 [RuCl2(p-cymene)]2/(S,R)-JOSIPHOS 催化从 1,2-二醇对映选择性合成 β-氨基醇。几种 1,2-二醇用仲胺处理，得到相应的光学活性 β-氨基醇，产率高达 99%，ee 为 77%。