1-(1-hydroxyethyl)naphthalen-2-ol | 165602-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-hydroxyethyl)naphthalen-2-ol
• 英文别名: 2-Hydroxy-I+/--methyl-1-naphthalenemethanol
• CAS: 165602-59-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: VSRKMRHVEZMOOP-UHFFFAOYSA-N

物化性质

• 沸点：
  339.1±9.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-(1-hydroxyethyl)naphthalen-2-ol 在 phenyltrimethylammonium tribromide 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 1-溴-2-萘酚
  参考文献：
  名称：

  Regioselective C(sp ² )−C(sp ³ ) Oxidative Bond Cleavage of 1‐(1‐Hydroxyalkyl) naphthalen‐2‐ols: First Synthesis of 1‐Azido‐halo‐naphthalene‐2(1 H )‐ones

  摘要：

  AbstractA new one‐pot oxidative cleavage of C(sp2)−C(sp3) bond has been explored using two complementary protocols employing Phenylselenyl bromide (PhSeBr) as well as Phenyltrimethylammonium Tribromide (PTAB), with much greater efficiency and scope. The oxidative cleavage proceeds via a dearomatization step to afford potentially useful bromonaphthols along with corresponding aldehydes. In this course, we also described the first synthesis of synthetically important azido‐halo naphthaleneones.

  DOI：

  10.1002/ijch.202000082
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.25h， 以55%的产率得到1-(1-hydroxyethyl)naphthalen-2-ol
  参考文献：
  名称：

  [EN] SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX
  [FR] INHIBITEURS À PETITES MOLÉCULES D'UN COMPLEXE PROTÉIQUE

  摘要：

  通过给予结合到KRIT1以抑制与HEG1结合的化合物的治疗血栓形成、炎症和动脉粥样硬化的组合物和方法。

  公开号：

  WO2020247608A1

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 Photooxygenation of Chiral Naphthyl Alcohols: The Hydroxy Group Directing Effect in Singlet Oxygen [4+2] Cycloaddition to Arenes
  作者：Waldemar Adam、Eva Maria Peters、Karl Peters、Michael Prein、Hans Georg von Schnering

  DOI：10.1021/ja00130a006

  日期：1995.6

  A series of chiral naphthyl alcohol derivatives 1 was prepared and submitted to sensitized photooxygenation. The corresponding endoperoxides 2 were formed in high yields through [4 + 2] cycloaddition of singlet oxygen. The pi-facial selectivity of singlet oxygen attack was determined and the stereochemistry of the product assigned for representative cases (1a,h) by X-ray analysis of the triols 3 derived from the endoperoxides by reduction. In the photooxygenation of the alcohols 1a-g in nonpolar solvents, the (alpha R*,1R*,4S*)-configurated endoperoxides 2a-g were formed preferentially (diastereomeric ratio (dr) greater than or equal to 85:15). Increase in solvent polarity or protection of the hydroxy group as the acetate in 1i or as the silyl ether in 1j led to substantial loss of diastereoselectivity. Placement of a methyl group at C2, as in alcohol 1h, gave high but opposite pi-facile selectivity (dr = 94:6), i.e., (alpha R*,1S*,4R*)-2h was formed as major product. The observed substitution effects on the pi-facial selectivity are rationalized in terms of steric and electronic control. Thus, hydrogen bonding operates between the unprotected hydroxy group and the incoming singlet oxygen dienophile. Peri strain leads to an effective energy discrimination of the respective diastereomeric transition states and, consequently, high pi-facial selectivities. An alkyl substituent at C2, however, induces additional ortho strain of 1,3-allylic origin, which overrides the effect of peri strain to afford highly selectively the opposite stereoisomer.