1-[1-(2-甲氧基萘基)]乙醇 | 93139-48-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-[1-(2-甲氧基萘基)]乙醇
• 英文名称: 1-(2-methoxynaphthalen-1-yl)ethan-1-ol
• 英文别名: 1-(2-Methoxynaphthalen-1-yl)ethanol
• CAS: 93139-48-1
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: JHZABIIOCGHRDC-UHFFFAOYSA-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

• 作为反应物：
  描述：

  1-[1-(2-甲氧基萘基)]乙醇 在 氧气 、 tetraphenylporphyrin 作用下， 以 氘代氯仿 为溶剂， 反应 2.5h， 生成 1-(11-Methoxy-9,10-dioxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6,11-tetraen-1-yl)-ethanol
  参考文献：
  名称：

  Diastereoselective Photooxygenation of Chiral Naphthyl Alcohols: The Hydroxy Group Directing Effect in Singlet Oxygen [4+2] Cycloaddition to Arenes

  摘要：

  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.

  DOI：

  10.1021/ja00130a006
• 作为产物：
  描述：

  1-乙酰基-2-萘酚 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 1-[1-(2-甲氧基萘基)]乙醇
  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

• Synthesis of Spiroisoxazolines via an Oximation/Dearomatization Cascade under Air
  作者：Dengfeng Chen、Tianyu He、Yuan Huang、Jinyue Luo、Fei Wang、Shenlin Huang

  DOI：10.1021/acs.orglett.0c01429

  日期：2020.6.5

  transition-metal-free synthesis of spiroisoxazolines is outlined. This protocol provides, for the first time, a direct access to spiroisoxazolines from aryl (thio)ethers or (thio)phenols in one synthetic step via an oximation/dearomatization cascade. In this reaction, sodium nitrite plays dual roles: as a hydroxylamine source and also a precatalyst to promote the aerobic dearomatization. This methodology features

  概述了螺异恶唑啉的无过渡金属催化合成。该方案首次在一个合成步骤中通过肟化/脱芳香化反应的级联，直接从芳基（硫）醚或（硫）酚中获得螺异恶唑啉。在该反应中，亚硝酸钠起着双重作用：既是羟胺源，又是促进有氧脱芳香化作用的前催化剂。这种方法具有前所未有的底物范围，高收率，可扩展性，可持续的氧化剂和温和的条件。
• Secondary Benzylation Using Benzyl Alcohols Catalyzed by Lanthanoid, Scandium, and Hafnium Triflate
  作者：Masahiro Noji、Tomoko Ohno、Koji Fuji、Noriko Futaba、Hiroyuki Tajima、Keitaro Ishii

  DOI：10.1021/jo034255h

  日期：2003.11.1

  alkylation, and trifluoromethanesulfonic acid (triflic acid, TfOH) was also a good catalyst. The catalytic activity of metal triflates and TfOH increased in the order La(OTf)3 < Yb(OTf)3 < TfOH < Sc(OTf)3 < Hf(OTf)4. A mechanistic study was also performed. The reaction of 1-phenylethanol (4a) in the presence of Sc(OTf)3 in nitromethane gave an equilibrium mixture of 4a and bis(1-phenylethyl) ether (54). Addition

  仲苄醇和三氟甲磺酸金属盐（例如La，Yb，Sc和Hf三氟甲磺酸盐）在硝基甲烷中的结合是一种高效的仲苄基化系统。碳（芳族化合物，烯烃，乙酸烯醇酯），氮（酰胺衍生物）和氧（醇）亲核试剂的二级苄基化反应是在水中存在的情况下，用仲苄醇和0.01-1 mol％的三氟甲磺酸金属盐进行的。带有酸敏感官能团的仲苄醇和亲核试剂（例如，叔丁基二甲基甲硅烷氧基和乙酰氧基以及甲基和苄基酯）可用于烷基化。Hf（OTf）4是该烷基化反应最活跃的催化剂，三氟甲磺酸（三氟甲磺酸，TfOH）也是一种很好的催化剂。金属三氟甲磺酸酯和TfOH的催化活性按La（OTf）3 < Yb（OTf）3
• A Novel Synthetic Route to 2-Arylalkanoic Acids by a Ruthenium-Catalyzed Chemoselective Oxidation of Furan Rings
  作者：Keitaro Ishii、Masahiro Noji、Haruka Sunahara、Ken-ichi Tsuchiya、Tôru Mukai、Ayako Komasaka

  DOI：10.1055/s-0028-1083222

  日期：2008.12

  Friedel-Crafts alkylation of 2-methylfuran with 1-arylalkanols without employing anhydrous conditions. The chemoselective oxidation of the furan ring in 1-arylalkylfurans to carboxylic acid was then investigated. In a solvent system of hexane-EtOAc/H 2 O (1:3:4), the furan ring was selectively oxidized with 7 equivalents of NaIO 4 by using 0.5 mol% RuCl 3 as catalyst to give 2-arylalkanoic acids in good yields

  描述了一种从 1-芳基烷醇高效两步合成 2-芳基烷酸的方法。首先，通过金属三氟甲磺酸盐催化 2-甲基呋喃与 1-芳基烷醇在无水条件下的傅-克烷基化反应，以高收率合成 1-芳基烷基呋喃衍生物。然后研究了 1-芳烷基呋喃中的呋喃环化学选择性氧化为羧酸。在己烷-EtOAc/H 2 O (1:3:4) 溶剂体系中，以 0.5 mol% RuCl 3 为催化剂，用 7 当量 NaIO 4 选择性氧化呋喃环，以良好收率得到 2-芳基链烷酸. 钌氧化的选择性由己烷-EtOAc的溶剂比控制。
• Chiral N-heterocyclic carbenes as asymmetric acylation catalysts
  作者：Yumiko Suzuki、Kazuyuki Muramatsu、Kaori Yamauchi、Yasuko Morie、Masayuki Sato

  DOI：10.1016/j.tet.2005.09.071

  日期：2006.1

  N-heterocyclic carbenes are generated from C2-symmetric 1,3-bis(1-arylethyl)imidazolium salts and potassium tert-butoxide. These C2-symmetric imidazolidenyl carbenes catalyze enantioselective acylation of racemic secondary alcohols. The asymmetric acylation of 1-(1-naphthyl)ethanol was achieved in up to 68% ee of the acylated product, using (R,R)-1,3-bis[(1-naphthyl)ethyl]imidazolium tetrafluoroborate as a precursor

  由C 2对称的1，3-双（1-芳乙基）咪唑鎓盐和叔丁醇钾产生手性N-杂环卡宾。这些C 2对称的咪唑烷烯基碳烯催化外消旋仲醇的对映选择性酰化。使用（R，R）-1,3-双[（1-萘基）乙基]咪唑四氟硼酸酯作为前体，可以在不超过68％ee的酰化产物中实现1-（1-萘基）乙醇的不对称酰化。手性N-杂环卡宾和丙酸乙烯酯作为酰基供体。
• Nickel-Mediated Enantiospecific Silylation via Benzylic C–OMe Bond Cleavage
  作者：Venkadesh Balakrishnan、Vetrivelan Murugesan、Bincy Chindan、Ramesh Rasappan

  DOI：10.1021/acs.orglett.0c04316

  日期：2021.2.19