3-(4-(trifluoromethyl)phenyl)naphthalen-1-ol | 1412902-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(4-(trifluoromethyl)phenyl)naphthalen-1-ol
• 英文别名: 3-[4-(Trifluoromethyl)phenyl]naphthalen-1-ol
• CAS: 1412902-40-9
• 化学式: C₁₇H₁₁F₃O
• 分子量: 288.269
• InChiKey: RFRKPJYZJLSSNS-UHFFFAOYSA-N

物化性质

• 沸点：
  405.5±45.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 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：
  4

反应信息

• 作为产物：
  描述：

  1-(2-((4-(trifluoromethyl)phenyl)ethynyl)phenyl)ethan-1-one 在 cesium acetate 、 copper(l) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以69%的产率得到3-(4-(trifluoromethyl)phenyl)naphthalen-1-ol
  参考文献：
  名称：

  炔酮的化学和区域选择性催化剂控制的碳环化：1-茚满酮和1-萘酚的快速合成

  摘要：

  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。

  DOI：

  10.1002/chem.201901860

文献信息

• Concise Synthesis of 1-Naphthols under Mild Conditions through a Copper-Catalyzed Arylation of Methyl Ketones
  作者：Zhenbang Lou、Shu Zhang、Chao Chen、Xinlong Pang、Ming Li、Lirong Wen

  DOI：10.1002/adsc.201300728

  日期：2014.1.13

  A concise synthesis of 1‐naphthols via cyclization of o‐iodoacetophenones and methyl ketones has been realized under very mild conditions. The cyclization process is initiated by a rare copper‐catalyzed arylation of simple methyl ketones with ortho‐iodoacetophenones.

  在非常温和的条件下，已经可以通过邻碘苯乙酮和甲基酮的环合反应合成1-萘酚。环化过程是由稀有铜催化的简单甲基酮与邻碘苯乙酮的芳基化而引发的。
• Tandem carbon–carbon bond insertion and intramolecular aldol reaction of benzyne with aroylacetones: novel formation of 4,4′-disubstituted 1,1′-binaphthols
  作者：Kentaro Okuma、Ryoichi Itoyama、Ayumi Sou、Noriyoshi Nagahora、Kosei Shioj

  DOI：10.1039/c2cc36128k

  日期：——

  An efficient route to 4-aryl-2-naphthols from arynes and aroylacetones was developed by carbon-carbon bond insertion followed by an intramolecular aldol reaction and dehydration. Benzyne derived from 2-(trimethylsilyl)phenyl triflate reacted with benzoylacetones in refluxing acetonitrile to give 4-aryl-2-naphthols and 3-aryl-1-naphthols.

  通过碳-碳键插入，随后的分子内醛醇缩合反应和脱水，开发了从芳烃和芳酰基丙酮制备4-芳基-2-萘的有效途径。由2-（三甲基甲硅烷基）苯基三氟甲磺酸酯衍生的苯炔与苯甲酰基丙酮在回流的乙腈中反应，得到4-芳基-2-萘和3-芳基-1-萘。
• Ruthenium-catalyzed coupling of α-carbonyl phosphoniums with sulfoxonium ylides <i>via</i> C–H activation/Wittig reaction sequences
  作者：Tian Chen、Zhiqiang Ding、Yuqiu Guan、Ruike Zhang、Jinzhong Yao、Zhangpei Chen

  DOI：10.1039/d1cc00433f

  日期：——

  A Ru(II)-catalyzed coupling of various α-carbonyl phosphoniums with sulfoxonium ylides has been realized for the facile synthesis of 1-naphthols in good to excellent yields. This oxidant-free transformation proceeds through Ru-catalyzed C–H activation of phosphoniums, Ru-carbene insertion, and intramolecular Wittig reaction processes.

  已经实现了Ru（II）催化的各种α-羰基with与亚砜基sulf的偶联，以易于以良好至极佳的产率合成1-萘酚。这种无氧化剂的转化过程是通过Ru催化的C的C–H活化，Ru卡宾的插入以及分子内Wittig反应过程进行的。
• Cu‐catalyzed synthesis of 1‐naphthols with terminal alkynes and 2‐bromoaryl ketones
  作者：Peng Ma、Yuhang Wang、Jianhui Wang

  DOI：10.1002/aoc.6792

  日期：2022.9

  A Cu-catalyzed straightforward synthesis of 1-naphthols via an 6-endo-dig cyclization of terminal alkynes with 2-bromoaryl ketones in water is reported. The Cu(I) catalytic system tolerates various electron-withdrawing and electron-donating functional groups on both substrates and exhibits unique 6-endo-dig selectivity to give 1-naphthols in moderate to good yields.

  报道了通过末端炔烃与 2-溴芳基酮在水中的 6-endo-dig 环化，Cu 催化直接合成 1-萘酚。Cu(I) 催化体系在两种底物上都能耐受各种吸电子和给电子官能团，并表现出独特的 6-endo-dig 选择性，以中等至良好的产率提供 1-萘酚。
• Cu(II)-Catalyzed 6π-Photocyclization of Non-6π Substrates
  作者：Yanbin Zhang、Ruiwen Jin、Wenjie Kang、Hao Guo

  DOI：10.1021/acs.orglett.0c01854

  日期：2020.7.17

  This research successfully achieved a Cu(II)-catalyzed 6 pi-photocyclization of non-6 pi substrates. The photo-enolization converts ortho-alkylphenyl alkynl ketones into a triene-type intermediate which undergoes the subsequent 6 pi-photo- facilitates both photoenolization and 6 pi-photocyclization. This research highlighted the tandem reaction strategy and the importance of metal catalysis in photochemistry.