(S)-1-(4-methyl-1-naphthyl)ethanol | 1104394-88-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1-(4-methyl-1-naphthyl)ethanol
• 英文别名: (1S)-1-(4-methylnaphthalen-1-yl)ethan-1-ol；(1S)-1-(4-methylnaphthalen-1-yl)ethanol
• CAS: 1104394-88-8
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: BZCMVGFPXPZLBO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-methyl-1-naphthyl)ethanol 在 氧气 、 tetraphenylporphyrin 作用下， 以 氘代氯仿 为溶剂， 反应 4.0h， 生成 (R)-1-((1S,8R)-8-Methyl-9,10-dioxa-tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5,11-tetraen-1-yl)-ethanol 、 (S)-1-((1S,8R)-8-Methyl-9,10-dioxa-tricyclo[6.2.2.0^2,7]dodeca-2(7),3,5,11-tetraen-1-yl)-ethanol
  参考文献：
  名称：

  Diastereoselective [4 + 2] cycloaddition of singlet oxygen in the photooxygenation of chiral naphthyl alcohols: evidence for a hydroxy group-directing effect

  摘要：

  DOI：

  10.1021/ja00062a049
• 作为产物：
  描述：

  4-甲基-1-萘乙酮 在 (1S,2S)-N-{N-methyl-N-[2-(η⁶-p-tolyl)ethyl]sulfamoyl}-1,2-diphenylethylenediamine hydrochloride ruthenium(II) dichloride dimer 作用下， 反应 15.0h， 以100%的产率得到(S)-1-(4-methyl-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

• 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.
• Diastereoselective [4 + 2] cycloaddition of singlet oxygen in the photooxygenation of chiral naphthyl alcohols: evidence for a hydroxy group-directing effect
  作者：Waldemar Adam、Michael Prein

  DOI：10.1021/ja00062a049

  日期：1993.5