(S)-1-(4-methoxy-1-naphthyl)ethanol | 1427565-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(4-methoxy-1-naphthyl)ethanol
• 英文别名: 1-(4-methoxynaphthalen-1-yl)ethan-1-ol；(1S)-1-(4-methoxynaphthalen-1-yl)ethan-1-ol；(1S)-1-(4-methoxynaphthalen-1-yl)ethanol
• CAS: 1427565-85-2
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: VFAWJOBDNPJYHT-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基-1-萘甲腈 在 (1S,2S)-N-{N-methyl-N-[2-(η⁶-p-tolyl)ethyl]sulfamoyl}-1,2-diphenylethylenediamine hydrochloride ruthenium(II) dichloride dimer 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.0h， 生成 (S)-1-(4-methoxy-1-naphthyl)ethanol
  参考文献：
  名称：

  Asymmetric Transfer Hydrogenation of 1-Naphthyl Ketones by an ansa-Ru(II) Complex of a DPEN-SO₂N(Me)-(CH₂)₂(η⁶-p-Tol) Combined Ligand

  摘要：

  The first second-generation designer Ru(II) catalyst 1b featuring an enantiopure N,C-(N-ethylene-N-methyl-sulfamoyI)-tethered (DPEN-k(2)N,N)/n(6)toluene hybrid ligand Is introduced. Using an SIC 1000 in HCO2H Et3N 5:2 transfer hydrogenation medium, secondary 1-naphthyl alcohols are obtained in up to >99.9% ee under mild conditions. Mechanistic factors are discussed.

  DOI：

  10.1021/ol400393j

文献信息

• Kinetic Resolution of Secondary Alcohols Catalyzed at the Exterior of Chiral Coordinated Capsules
  作者：Kentaro Harada、Ryo Sekiya、Takeharu Haino

  DOI：10.1002/chem.202304244

  日期：2024.2.21

  The confinement of the chiral space inside a molecular host is an ideal platform for enantioselective reactions. However, this concept significantly limits the scope of reactants because reactants must be trapped inside molecular hosts. Instead, we utilized the exteriors of chiral molecular capsules as chiral sources and realized the kinetic resolution of secondary alcohols.

  分子主体内部手性空间的限制是对映选择性反应的理想平台。然而，这个概念极大地限制了反应物的范围，因为反应物必须被捕获在分子主体内。相反，我们利用手性分子胶囊的外部作为手性源，实现了仲醇的动力学拆分。
• Asymmetric Transfer Hydrogenation of 1-Naphthyl Ketones by an <i>ansa</i>-Ru(II) Complex of a DPEN-SO₂N(Me)-(CH₂)₂(η⁶-<i>p</i>-Tol) Combined Ligand
  作者：Andrea Kišić、Michel Stephan、Barbara Mohar

  DOI：10.1021/ol400393j

  日期：2013.4.5

  The first second-generation designer Ru(II) catalyst 1b featuring an enantiopure N,C-(N-ethylene-N-methyl-sulfamoyI)-tethered (DPEN-k(2)N,N)/n(6)toluene hybrid ligand Is introduced. Using an SIC 1000 in HCO2H Et3N 5:2 transfer hydrogenation medium, secondary 1-naphthyl alcohols are obtained in up to >99.9% ee under mild conditions. Mechanistic factors are discussed.