1-(6-Methoxy-1-naphthyl)-ethanol | 58149-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(6-Methoxy-1-naphthyl)-ethanol
• 英文别名: 1-(6-Methoxy-2-napthyl)ethanol；1-(6-methoxynaphthalen-1-yl)ethanol
• CAS: 58149-98-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: QFXCCHAKLQUGAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  355.6±17.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

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：

  6-羟基-1-萘甲酸 在 sodium tetrahydroborate 、 水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 34.08h， 生成 1-(6-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

• The Substituent Effect. XI. Solvolysis of 5-, 6-, and 7-Substituted 1-(1-Naphthylethyl) Chlorides
  作者：Yuho Tsuno、Masami Sawada、Takahiro Fujii、Yoshihiko Tairaka、Yasuhide Yukawa

  DOI：10.1246/bcsj.48.3356

  日期：1975.11

  Fourteen 5-, 6-, and 7-substituted 1-(1-naphthylethyl) chlorides were prepared and the solvolysis rates were determined in 80% (v/v) aqueous acetone at 45 °C. The effects of −R substituents at respective positions were treated on the basis of the equation, logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+). The position dependency of the inductive effect was given by Cij(=ρi⁄ρi,4α); C3α=1.37, C4α=1.00, C5α=0.75, C6α=0.57, and C7α=0.72. The Cij values appear to be correlated with Dewar’s simplified field function 1/rij. The position dependency of Pi-electronic effect given by the ratio ρπ+⁄ρi,4α=qr·ij+ was consistent with the prediction from the MO indices, such as Forsyth’s Δqij(ArCH2+ parameters. The same treatment was applied also to three other naphthalene reactivities, detritiation, pKa of α-naphthoic acids and pKa of naphthylammonium ions. The linear ρi–ρi relation holds among these reactions, suggesting a reaction-independent scheme of the inductive transmission. The qr·ij+ values vary at conjugate positions with reaction but not at non-conjugate positions irrespective of reactions. The results are discussed in comparison with those of relevant treatments.

  制备了十四个5-、6-和7-取代的1-(1-萘乙基)氯化物，并在45°C下，80%（体积/体积）的乙酸水溶液中测定了其溶剂分解速率。基于方程logk⁄k0=ρiσi+ρx+σx+=ρ(Cijσi+qrij+σπ+)，处理了在相应位置上的−R取代基的影响。诱导效应的位置依赖性由Cij(=ρi⁄ρi,4α)给出；C3α=1.37，C4α=1.00，C5α=0.75，C6α=0.57，C7α=0.72。Cij值似乎与Dewar的简化场函数1/rij相关。由比率ρπ+⁄ρi,4α=qr·ij+给出的π电子效应的位置依赖性与从MO指数（如Forsyth的Δqij(ArCH2+参数）的预测一致。同样的处理也应用于其他三种萘的反应性：脱氢、α-萘甲酸的pKa和萘甲基铵离子的pKa。在这些反应中，线性ρi–ρi关系成立，表明诱导传递的反应独立方案。qr·ij+值在共轭位置随反应变化，但在非共轭位置不随反应变化。结果在与相关处理的比较中进行了讨论。
• Process for the preparation of 2-aryl propionic acids
  申请人：Chaudhari Vitthal Raghunath

  公开号：US20050283020A1

  公开（公告）日：2005-12-22

  The present invention provides for the preparation of 2-aryl propionic acids, which comprises the steps of: reacting an aryl compound selected from an arylalkyl halide having general formula I, aryl alcohol having general formula II or aryl substituted olefins having general formula III, as shown in the accompanying drawings, wherein, R 1 is aryl, substituted aryl, naphthyl or substituted naphthyl groups, R 2 , R 3 , R 4 and R 5 are independently hydrogen, alkyl, aryl, arylalkyl or cycloaliphatic groups with or without substituents and X is other a halogen atom selected from chlorine, bromine, iodine with a halide promoter, an organic acid, water and a palladium catalyst in an organic solvent selected from ketones or cyclic ethers in carbon monoxide atmosphere under homogeneous conditions, at a temperature ranging between 30 to 130° C., for a period ranging between 0.3 to 4 hrs, at pressures ranging between 50 to 1500 psig, cooling the reaction mixture to ambient temperature, flushing the reaction vessel with inert gas, removing the solvent by conventional methods, and separating the catalyst and isolating 2 aryl propionic acid having formula IV as shown in the accompanying drawings, wherein, R 1 is aryl, substituted aryl, naphthyl or substituted naphthyl groups, R 2 , R 3 , R 4 and R 5 are independently hydrogen, alkyl, aryl, arylalkyl, cycloaliphatic groups with or without substituents.

  本发明提供了制备2-芳基丙酸的方法，包括以下步骤：在伴随的图示中显示的通用式I具有芳基烷基卤化物、通用式II具有芳基醇或通用式III具有芳基取代烯烃中选择的芳基化合物反应，其中，R1为芳基、取代芳基、萘基或取代萘基，R2、R3、R4和R5独立地为氢、烷基、芳基、芳基烷基或环脂族基，带或不带取代基，X为氯、溴、碘等卤素原子，通过在选择的酮或环醚有机溶剂中，在一氧化碳气氛下均相条件下，以温度在30至130°C范围内、反应时间在0.3至4小时范围内、压力在50至1500 psig范围内的条件下，与卤化促进剂、有机酸、水和钯催化剂反应，冷却反应混合物至室温，用惰性气体冲洗反应容器，通过常规方法去除溶剂，并分离催化剂并分离出具有通用式IV的2-芳基丙酸，其中，R1为芳基、取代芳基、萘基或取代萘基，R2、R3、R4和R5独立地为氢、烷基、芳基、芳基烷基、环脂族基，带或不带取代基。
• METHOD FOR FRACTIONATING STEREOISOMERIC COMPOUNDS
  申请人：Jakel Christoph

  公开号：US20090030235A1

  公开（公告）日：2009-01-29

  The present invention relates to a method for fractionating stereoisomeric compounds which have at least one alcohol and/or amino group.

  本发明涉及一种用于分离具有至少一种醇和/或氨基团的立体异构化合物的方法。
• Process for the enantioselective preparation of secondary alcohols by lipase-catalyzed solvolysis of the corresponding acetoacetic esters
  申请人：Popp Alfred

  公开号：US20050032182A1

  公开（公告）日：2005-02-10

  Process for the enantioselective preparation of secondary alcohols, wherein a racemic or enantiomerically enriched mixture of acetoacetic esters of chiral secondary alcohols is subjected to enantioselective enzymatic solvolysis in the presence of a nucleophile and a lipase capable of the solvolytic cleavage of an ester group.

  手性二级醇的对映选择性制备过程，其中手性二级醇的乙酰乙酸酯的混合物（消旋或对映富集）在核苷酸和一种能够溶解酯基的脂肪酶存在下，经过对映选择性酶促溶解反应。
• Verfahren zur Herstellung von stereoisomeren Carbonsäureestern
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP1031629A2

  公开（公告）日：2000-08-30

  Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von stereoisomeren Carbonsäureestern bestehend aus einer Säure- und einer Alkohol-Komponente mit jeweils mindestens einem chiralen Zentrum, wobei mindestens ein Stereoisomer des Carbonsäureesters in einem Überschuß vorliegt, indem man einen racemischen Carbonsäureester mit einem racemischen Alkohol in Gegenwart einer Carboxylesterhydrolase (EC 3.1.1) umsetzt.

  本发明涉及一种制备立体异构体羧酸酯的工艺，羧酸酯由一种酸和一种醇组成，每种酸和醇至少有一个手性中心，在羧酸酯水解酶（EC 3.1.1）存在下，外消旋羧酸酯与外消旋醇反应，其中至少有一种羧酸酯的立体异构体过量存在。