(S)-3-hydroxy-1-morpholinobutan-1-one | 518358-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (S)-3-hydroxy-1-morpholinobutan-1-one
• 英文别名: 3-hydroxy-1-morpholinobutan-1-one；(3S)-3-hydroxy-1-morpholin-4-ylbutan-1-one
• CAS: 518358-77-5
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: HUMACWIMWGVBGQ-ZETCQYMHSA-N

物化性质

• 沸点：
  348.3±37.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-乙酰丙酮吗啉 在 [RuCl(benzene)(S)-SunPhos]Cl 、 氢气 作用下， 以 四氢呋喃 为溶剂， 70.0 ℃ 、2.0 MPa 条件下， 反应 8.0h， 生成 (S)-3-hydroxy-1-morpholinobutan-1-one
  参考文献：
  名称：

  Ru-Catalyzed Asymmetric Hydrogenation of 3-Oxoglutaric Acid Derivatives via Solvent-Assisted Pinpoint Recognition of Carbonyls in Close Chemical Propinquity

  摘要：

  Upon comparison of hydrogenation rates of various beta-ketocarboxylic acid derivatives, beta-ketoamides were found to be hydrogenated slightly faster than beta-ketoesters in EtOH in the presence of [RuCl(benzene)(S)-SunPhos]Cl at 70 degrees C with 20 bar of hydrogen. In THF these differences were so sharpened that beta-ketoamides were hydrogenated even faster than In EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.

  DOI：

  10.1021/ol201406w

文献信息

• Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds
  作者：Gary A. Molander、Steven R. Wisniewski、Mona Hosseini-Sarvari

  DOI：10.1002/adsc.201300640

  日期：2013.10.11

  Enantioenriched potassium beta-trifluoroboratoamides have been synthesized via an asymmetric, copper-catalyzed 1,4-addition of tetrahydroxydiboron (BBA) and tetrakis(dimethylamino)diboron to alpha,beta-unsaturated amides. These dibora reagents provide access to the desired organotrifluoroborates using effective and atom economical sources of boron. The copper-catalyzed beta-boration is extended to

  Enantioenriched 钾β-trifluoroboratoamides 已通过不对称、 铜催化1,4-加成四羟基二硼(BBA) 和四(二甲氨基) 二硼合成α，β-不饱和酰胺。这些二硼试剂使用有效且原子经济的硼源提供了获得所需有机三氟硼酸盐的途径。铜催化的 β-硼酸化扩展到 α,β-不饱和酮和酯。合成的有机三氟硼酸钾的产率高达 92%，对映体比例高达 98:2。当金属转移通过 SE2 机制通过开放过渡态进行时，富含对映体的 β-三氟硼酰胺钾与一系列芳基和杂芳基氯化物成功交叉偶联，具有完全立体化学保真度。
• Nonenzymatic Kinetic Resolution of 3-Hydroxyalkanamides with Chiral Copper Catalyst
  作者：Osamu Onomura、Yosuke Demizu、Yuki Kubo、Yoshihiro Matsumura

  DOI：10.1055/s-2008-1032057

  日期：2008.2

  Kinetic resolution of 3-hydroxyalkanamides with good to high selectivities was achieved by benzoylation using copper(II) triflate and (R,R)-PhBox [2,2′-isopropylidenebis(4-phenyl-2-oxazoline)] as catalyst, which also mediated enantioselective tosylation of 2,2-bis(hydroxymethyl)alkanamides with high efficiency.

  使用三酸铜（II）和 (R,R)-PhBox [2,2′-异亚丙基双（4-苯基-2-恶唑啉）] 作为催化剂，通过苯甲酰化作用实现了 3-羟基烷酰胺的动力学解析，并具有良好至高的选择性。