1-萘醇,3-甲基-2-苯基- | 108695-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-萘醇,3-甲基-2-苯基-
• 英文名称: 3-methyl-2-phenylnaphthalen-1-ol
• 英文别名: 3-Methyl-2-phenyl-1-naphthalenol
• CAS: 108695-48-3
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: KWFQMNXZZKUQQX-UHFFFAOYSA-N

物化性质

• 沸点：
  377.1±11.0 °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：

  1-萘醇,3-甲基-2-苯基- 、 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-3-methyl-2-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：

  2-phenyl-1-(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 5.0h， 以82%的产率得到1-萘醇,3-甲基-2-苯基-
  参考文献：
  名称：

  铂催化的2-炔基-1-乙酰苯的化学选择性水合二聚反应，用于一锅轻松地合成丙烯衍生物。

  摘要：

  我们报告了通过PtCl 2催化的一锅合成的chrysene化合物的2-炔基-1-乙酰苯的易水合二聚化。这种新的串联催化包括炔的初始选择性水合，然后是二酮中间体的化学选择性二聚。13 C标记实验以及反应中间体的分离已阐明了这种环化的机理。

  DOI：

  10.1021/jo701580r

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006002185A1

  公开（公告）日：2006-01-05

  The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel naphthalene compounds that are particularly useful for selective estrogen receptor modulation.

  本发明涉及一种具有多种治疗用途的新化合物，更具体地说是一种新的萘化合物，特别适用于选择性雌激素受体调节。
• Nitrone Directing Groups in Rhodium(III)-Catalyzed C−H Activation of Arenes: 1,3-Dipoles versus Traceless Directing Groups
  作者：Fang Xie、Songjie Yu、Zisong Qi、Xingwei Li

  DOI：10.1002/anie.201609658

  日期：2016.12.5

  Functionalizable directing groups (DGs) are highly desirable in C−H activation chemistry. The nitrone DGs are explored in rhodium(III)‐catalyzed C−H activation of arenes and couplings with cyclopropenones. N‐tert‐butyl nitrones bearing a small ortho substituent coupled to afford 1‐naphthols, where the nitrone acts as a traceless DG. In contrast, coupling of N‐tert‐butyl nitrones bearing a bulky ortho

  在CH活化化学中，高度可官能化的导向基团（DG）是非常理想的。在铑（III）催化的芳烃的CH活化以及与环丙烯酮的偶联反应中探索了DG酮。N-叔丁基硝酮带有一个小的邻位取代基，偶联生成1-萘酚，其中硝基起无痕DG的作用。相反，带有庞大邻位基团的N-叔丁基硝酮的偶联遵循C–H酰化/ [3 + 2]偶极加成途径生成双环。N-芳基硝酮的偶联遵循相同的酰化/ [3 + 2]加成过程，但传递不同的双环。
• 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。
• CHEMICAL COMPOUNDS
  申请人：Heyer Dennis

  公开号：US20070276000A1

  公开（公告）日：2007-11-29

  The present invention relates to cycloalkylidene compounds with a variety of therapeutic uses, more particularly novel naphthalene compounds that are particularly useful for selective estrogen modulation.

  本发明涉及具有各种治疗用途的环烷基亚烯化合物，更具体地涉及新型萘化合物，特别适用于选择性雌激素调节。
• Naphthalene compounds as selective estrogen receptor modulators
  申请人：Glaxo Smith Kline LLC

  公开号：US07649093B2

  公开（公告）日：2010-01-19

  The present invention relates to cycloalkylidene compounds with a variety of therapeutic uses, more particularly novel naphthalene compounds that are particularly useful for selective estrogen receptor modulation.

  本发明涉及具有多种治疗用途的环烷基亚甲基化合物，更具体地涉及新型萘化合物，特别适用于选择性雌激素受体调节。