2-Methyl-3-phenyl-1-naphthol | 108695-45-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Methyl-3-phenyl-1-naphthol
• 英文别名: 2-methyl-3-phenylnaphthalen-1-ol
• CAS: 108695-45-0
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: IDIUBDOMFUFJLO-UHFFFAOYSA-N

物化性质

• 沸点：
  402.9±24.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  2-Methyl-3-phenyl-1-naphthol 、 碘甲烷 在 sodium hydroxide 、 苄基三乙基碘化铵 作用下， 以 二氯甲烷 为溶剂， 生成 1-methoxy-2-methyl-3-phenylnaphthalene
  参考文献：
  名称：

  Metal-Catalyzed Cyclopropene Rearrangements for Benzannulation: Evaluation of an Anthraquinone Synthesis Pathway and Reevaluation of the Parallel Approach via Carbene-Chromium Complexes

  摘要：

  The reaction of 3-arylcyclopropenes with Cr(CO)(6) and Mo(CO)(6) produces naphthols, in an example of metal-promoted benzannulation. Substituents at C-3 (in addition to aryl) have a strong effect on the success of the process: 3-H derivatives are generally effective, but the yields decrease for 3-alkyl derivatives as the size of the alkyl group increases. The 3,3-diphenyl and 3-cyano derivatives are unreactive. The mechanism is postulated to involve metal-complexed vinyl carbene units, parallel with the benzannulation reaction involving arylcarbene complexes with alkynes. The regioselectivity has been probed with various unsymmetrically 1,2-disubstituted 3-arylcyclopropenes. The results suggest a simple correlation with steric size, consistent with initial cleavage of the cyclopropene sigma bond bearing the smaller substituent. The result of this regioselectivity is a product structure showing a substituent arrangement opposite to that from the carbene-chromium approach; the smaller substituent of the cyclopropyl double bond ends up adjacent to the phenol OH in the product. Catalytic activity at low efficiency was observed, using a Mo(CO)a catalyst. However, the use of Mo(CO)(6) also promotes formation of indenes as significant byproducts at the expense of naphthalenes. Attempts to use the arylcyclopropene rearrangement to convert a 3-(1,4-dimethoxy-2-naphthyl)cyclopropene to an anthraquinone skeleton produced instead a phenanthrene via an unusual substitution for a methoxy substituent. A related example previously reported to produce anthraquinones via the naphthylcarbene-chromium/ alkyne reaction was shown to be in error; the correct structure is again a phenanthrone, and the product is exactly parallel with that observed in the cyclopropene rearrangement. A naphthoquinone substituted with a cyclopropene at C-2 does provide the first example of metal-promoted benzannulation to give an anthraquinone.

  DOI：

  10.1021/ja00095a014
• 作为产物：
  描述：

  1-phenyl-2-(2-(prop-1-ynyl)phenyl)ethanone 在 platinum(II) chloride 一氧化碳 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以31%的产率得到2-Methyl-3-phenyl-1-naphthol
  参考文献：
  名称：

  PtCl2催化三酮官能团的水合环化反应，形成双环螺酮。

  摘要：

  DOI：

  10.1002/anie.200700022

文献信息

• Studies on the Tandem Reaction of 4-Aryl-2,3-allenoates with Organozinc Reagents: A Facile Route to Polysubstituted Naphthols
  作者：Guobi Chai、Zhan Lu、Chunling Fu、Shengming Ma

  DOI：10.1002/chem.200901779

  日期：2009.10.26

  Diversified polysubstituted α‐naphthols have been efficiently constructed through a tandem reaction of easily available 2,3‐allenoates and organozinc reagents in moderate to excellent yields (see scheme). Some of the products may undergo a couple of sequential coupling reactions to afford polysubstituted naphthalenes.

  通过容易获得的2,3-烯丙酸酯和有机锌试剂的串联反应，以中等至极好的收率串联反应，可以有效地构建多样化的多取代α-萘酚（参见方案）。一些产物可能会经历几次顺序的偶联反应，以提供多取代的萘​​。
• Chemo‐ and Regioselective Catalyst‐Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1‐Indanones and 1‐Naphthols
  作者：Liangliang Song、Guilong Tian、Erik V. Van der Eycken

  DOI：10.1002/chem.201901860

  日期：2019.6.7

  A catalyst‐controlled intramolecular carbocyclization of 2‐alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1‐indanones are formed through 5‐exo‐dig carbocyclizations with exclusive chemo‐, regio‐ and stereoselectivity. When catalyzed by copper(I), 1‐naphthols are obtained through 6‐endo‐dig carbocyclizations with exclusive chemo‐ and regioselectivity.

  提出了一种由催化剂控制的2-炔基芳基酮的分子内碳环化反应。下铑（III）催化，1-茚满酮是通过5-形成外切-挖独家化疗选择性，区域选择性和立体选择性carbocyclizations。当由铜催化的（I），1-萘酚通过6-得到内型-挖独家化疗和区域选择性carbocyclizations。
• Sequential and regioselective Friedel–Crafts reactions of gem-dihalogenocyclopropanecarbonyl chlorides with benzenes for the synthesis of 4-aryl-1-naphthol derivatives
  作者：Yoshinori Nishii、Yoo Tanabe

  DOI：10.1039/a605030a

  日期：——

  Novel, sequential and regioselective Friedel–Crafts type reactions of (E)-3-aryl-2,2-dihalogenocyclopropanecarbonyl chlorides 1 and 2,2-dichlorocyclopropanecarbonyl chlorides 3 with benzenes produce various 4-aryl-3-halogeno-1-naphthols 2 and 4-aryl-1-naphthols 4, respectively. One of the benzannulations involves the intramolecular cyclization of acid chlorides 1, followed by intermolecular coupling with substituted benzenes to give 4-aryl-3-halogeno-1-naphthols 2. As a demonstration of this annulation, 4-aryl-3-bromo-1-naphthols 2i and 2k are successfully converted into new analogues of 1-aryl-3-hydroxymethyl-4-methoxy-2-naphthoic acid lactones 13, a class of lignan lactones. The other benzannulation involves three series of reactions using acid chlorides 3a–c: (1) the intermolecular Friedel–Crafts acylation of 3 with one benzene molecule giving the intermediary 2,2-dichlorocyclopropyl(phenyl)methanones 14a–c; (2) the intermolecular trapping of 14a–c with another benzene molecule accompanied by regioselective ring opening; and (3) the final intramolecular cyclization giving 4-phenyl-1-naphthols 4a–c. The use of p-xylene also gives the corresponding 4-(p-xylyl)-1-naphthol 4d. The reactions of alternatively prepared ketones 14 with benzenes gives a variety of ‘unsymmetrically’ substituted 4-aryl-1-naphthols 4c,e–k under identical conditions. However, the reaction using p-methoxyphenyl ketone analogues 14g does not produce 4-aryl-1-naphthols, but gives 5-aryl-2-(p-methoxyphenyl)-3-methylfurans 16. These annulations proceed straightforwardly (in a one-pot manner) and this variation is due to the highly regioselective cyclopropane ring-openings.

  新颖的、顺序的以及区域选择性的Friedel-Crafts类反应，通过苯与(E)-3-芳基-2,2-二卤代环丙烷羧酰氯1和2,2-二氯环丙烷羧酰氯3发生反应，生成各种4-芳基-3-卤代-1-萘醇2和4-芳基-1-萘醇4。其中一类苯环增殖反应涉及酸氯1的分子内环化，随后与取代苯的分子间耦合，生成4-芳基-3-卤代-1-萘醇2。作为这一环增殖反应的示范，成功将4-芳基-3-溴-1-萘醇2i和2k转化为新的1-芳基-3-羟甲基-4-甲氧基-2-萘酸内酯类化合物13，这是一类木质素内酯。另一类苯环增殖反应涉及使用酸氯3a-c进行三系列反应：（1）与一个苯分子的分子间Friedel-Crafts酰基化反应，得到中间体2,2-二氯环丙基（苯基）甲酮14a-c；（2）与另一个苯分子的分子间捕捉14a-c，伴随区域选择性的开环；（3）最终的分子内环化反应生成4-苯基-1-萘醇4a-c。使用对二甲苯也能得到相应的4-(对二甲基基)-1-萘醇4d。交替制备的酮14与苯的反应在相同条件下生成多种“不对称”取代的4-芳基-1-萘醇4c,e-k。然而，使用对甲氧基苄基酮类化合物14g的反应并不产生4-芳基-1-萘醇，而是生成5-芳基-2-(对甲氧基苄基)-3-甲基呋喃16。这些环增殖反应在单锅条件下直接进行，这种变化是由于高度区域选择性的环丙烷开环反应造成的。
• Preparation of 1-naphthols from acetylenes and o-phthalaldehyde using low-valent tantalum and niobium.
  作者：Yasutaka Kataoka、Jiro Miyai、Makoto Tezuka、Kazuhiko Takai、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)94557-x

  日期：1990.1

  Tantalum (or niobium)-alkyne complexes are produced by treatment of acetylenes with the low-valent tantalum (niobium) derived by zinc reduction of TaCl5 (NbCl5). Substituted 1-naphthols are prepared regioselectively by reaction of o-phthalaldehyde with the tantalum (or niobium)-alkyne complexes in good to excellent yields.

  钽（或铌）-炔烃配合物是通过用低价钽（铌）处理乙炔而制得的，该钽由铌还原TaCl 5（NbCl 5）生成。通过邻苯二甲醛与钽（或铌）-炔烃配合物的反应，可以高选择性地制备取代的1-萘酚。
• Metal carbonyl-promoted rearrangement of cyclopropenes to naphthols
  作者：M. F. Semmelhack、Suzzy Ho、Michael Steigerwald、M. C. Lee

  DOI：10.1021/ja00248a047

  日期：1987.7