(-)-1-(4-hydroxymethylphenyl)ethanol | 1312214-65-5

• 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: (-)-1-(4-hydroxymethylphenyl)ethanol
• 英文别名: (1S)-1-[4-(hydroxymethyl)phenyl]ethanol
• CAS: 1312214-65-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: OZHROFCXIMHHRO-ZETCQYMHSA-N

物化性质

• 沸点：
  300.2±22.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [RuH((R,R)-NH(CH(Ph))₂NH₂)((R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl)] 、 (-)-1-(4-hydroxymethylphenyl)ethanol 以 氘代四氢呋喃 为溶剂， 以100%的产率得到
  参考文献：
  名称：

  Experimental Investigations of a Partial Ru–O Bond during the Metal–Ligand Bifunctional Addition in Noyori-Type Enantioselective Ketone Hydrogenation

  摘要：

  The transition state for the metal ligand bifunctional addition step in Noyori's enantioselective ketone hydrogenation was investigated using intramolecular trapping experiments. The bifunctional addition between the Ru dihydride trans-[Ru((R)-BINAP)(H())2((R,R)-dpen)] and the hydroxy ketone 4-HOCH2C6H4(CO)CH3 at -80 degrees C exclusively formed the corresponding secondary ruthenium alkoxide trans-[Ru((R)-BINAP)(H)(4-HOCH2C6H4CH(CH3)O)((R,R)-dpen)]. Combined with the results of control experiments, this observation provides strong evidence for the formation of a partial Ru-O bond in the transition state.

  DOI：

  10.1021/ja202732q
• 作为产物：
  描述：

  (4-(2-methyl-1,3-dioxolan-2-yl)phenyl)methanol 在 盐酸 、 trans-[Ru((R)-3,5-xylyl-BINAP)(Cl₂)((R)-DAIPEN)] 、 potassium tert-butylate 、 水 、 氢气 作用下， 以 异丙醇 为溶剂， 20.0~30.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 (-)-1-(4-hydroxymethylphenyl)ethanol
  参考文献：
  名称：

  Experimental Investigations of a Partial Ru–O Bond during the Metal–Ligand Bifunctional Addition in Noyori-Type Enantioselective Ketone Hydrogenation

  摘要：

  The transition state for the metal ligand bifunctional addition step in Noyori's enantioselective ketone hydrogenation was investigated using intramolecular trapping experiments. The bifunctional addition between the Ru dihydride trans-[Ru((R)-BINAP)(H())2((R,R)-dpen)] and the hydroxy ketone 4-HOCH2C6H4(CO)CH3 at -80 degrees C exclusively formed the corresponding secondary ruthenium alkoxide trans-[Ru((R)-BINAP)(H)(4-HOCH2C6H4CH(CH3)O)((R,R)-dpen)]. Combined with the results of control experiments, this observation provides strong evidence for the formation of a partial Ru-O bond in the transition state.

  DOI：

  10.1021/ja202732q

文献信息

• Manganese Transfer Hydrogenases Based on the Biotin‐Streptavidin Technology
  作者：Weijin Wang、Ryo Tachibana、Zhi Zou、Dongping Chen、Xiang Zhang、Kelvin Lau、Florence Pojer、Thomas R. Ward、Xile Hu

  DOI：10.1002/anie.202311896

  日期：2023.10.23

  Efficient Mn artificial transfer hydrogenases (ATHases) were developed using the biotin-streptavidin technology, which exhibits high activity and enantioselectivity for the transfer hydrogenation of a wide range of aryl ketones. The S112Y-K121 M double mutation and the appropriate chemical structure of the Mn cofactor play critical roles in the reactivity and enantioselectivity of the enzymes.

  利用生物素-链霉亲和素技术开发了高效的锰人工转移氢化酶（ATHases），该酶对多种芳基酮的转移氢化表现出高活性和对映选择性。S112Y-K121 M 双突变和 Mn 辅因子的适当化学结构在酶的反应性和对映选择性中发挥着关键作用。