4-fluoro-2-(1-phenylvinyl)phenol | 1275593-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-2-(1-phenylvinyl)phenol
• 英文别名: 4-Fluoro-2-(1-phenylethenyl)phenol；4-fluoro-2-(1-phenylethenyl)phenol
• CAS: 1275593-35-5
• 化学式: C₁₄H₁₁FO
• 分子量: 214.239
• InChiKey: LURKNOIMZZRYMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-fluoro-2-(1-phenylvinyl)phenol 在 Rh(COD)[(R,S)-DuanPhos]BF₄ 、 氢气 、 三乙胺 作用下， 以 甲苯 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 4.0h， 以99%的产率得到(S)-4-fluoro-2-(1-phenylethyl)phenol
  参考文献：
  名称：

  Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups

  摘要：

  A new synthetic strategy that turns styrene-type olefins into excellent substrates for Rh-catalyzed asymmetric hydrogenation by Installing a 2'-hydroxyl substituent is described. This methodology accommodates trisubstituted olefinic substrates in various E/Z mixtures, leading to valuable benzylic chiral compounds including (R)-tolterodine. It is also demonstrated that the 2'-hydroxyl groups could be readily removed in high yield without loss of ee from the products. Thus, this technology represents an attractive alternative to the Ir(P-N) catalyst system for the asymmetric hydrogenation of unfunctionalized olefins.

  DOI：

  10.1021/ol200422p
• 作为产物：
  描述：

  苯乙酮 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 sodium acetate 、 lithium tert-butoxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.0h， 生成 4-fluoro-2-(1-phenylvinyl)phenol
  参考文献：
  名称：

  铑（III）催化N-苯氧基乙酰胺与N-甲苯磺酰hydr或重氮酸酯通过C ？H激活

  摘要：

  的偶联反应Ñ -phenoxyacetamides与Ñ -tosylhydrazones或通过铑diazoesters III催化的Ç  H被报道活化。在该反应中，获得了高收率的邻链烯基苯酚，并且具有出色的区域选择性和立体选择性。Rh-卡宾迁移插入被认为是反应机理中的关键步骤。

  DOI：

  10.1002/anie.201309650

文献信息

• B(C ₆ F ₅ ) ₃ ‐Catalyzed Hydroarylation of Aryl Alkynes for the Synthesis of 1,1‐Diaryl and Triaryl Substituted Alkenes
  作者：Hui Chen、Liuzhou Gao、Xueting Liu、Guoqiang Wang、Shuhua Li

  DOI：10.1002/ejoc.202101001

  日期：2021.10.7

  B(C6F5)3-catalyzed hydroarylation of both terminal and internal alkynes leads to 1,1-diaryl and triaryl substituted alkenes. A B(C6F5)3-phenol adduct mediated protonation mechanism is responsible for the formation of the related alkenes as well as the observed stereoselectivity.

  B(C 6 F 5 ) 3 -催化的末端和内部炔烃的加氢芳基化产生1,1-二芳基和三芳基取代的烯烃。AB(C 6 F 5 ) 3 -苯酚加合物介导的质子化机制负责相关烯烃的形成以及观察到的立体选择性。
• Nickel catalyzed intramolecular oxidative coupling: synthesis of 3-aryl benzofurans
  作者：Sakshi Aggarwal、Dasari Srinivas、Chinnabattigalla Sreenivasulu、Gedu Satyanarayana

  DOI：10.1039/d0ra03071f

  日期：——

  transition metal-catalyzed reactions. Herein we have developed nickel-catalyzed synthesis of 3-aryl benzofurans from ortho-alkenyl phenols via intramolecular dehydrogenative coupling. Notably, simple O2 gas served as an oxidant, without using any sacrificial hydrogen acceptor. The strategy enabled the synthesis of 3-aryl benzofurans in good to excellent yields.

  最近的研究集中在过渡金属催化的反应上。在此，我们开发了通过分子内脱氢偶联从邻-烯基酚中镍催化合成 3-芳基苯并呋喃。值得注意的是，简单的 O 2气体用作氧化剂，没有使用任何牺牲的氢受体。该策略能够以良好至优异的产率合成 3-芳基苯并呋喃。
• Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2<i>H</i>-Chromenes
  作者：Nengneng Zhou、Ziqin Xia、Kaimo Kuang、Qiankun Xu、Fangli Zhao、Lei Wang、Man Zhang

  DOI：10.1021/acs.orglett.2c02314

  日期：2022.8.12

  A novel visible-light-mediated difluoroalkylation of 1-(allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-arylvinyl)-2-(vinyloxy)benzenes for the synthesis of bis-difluoroalkylated benzoxepines and 2H-chromenes is developed. This method features mild reaction conditions, good regioselectivity, a wide substrate scope, good functional-group compatibility, and late-stage modification. Preliminary mechanistic

  1-(烯丙氧基)-2-(1-芳基乙烯基)苯和1-(1-芳基乙烯基)-2-(乙烯基氧基)苯的新型可见光介导二氟烷基化合成双-二氟烷基苯并氧杂环庚烷和2 H-开发了色烯。该方法具有反应条件温和、区域选择性好、底物范围广、官能团相容性好、后期修饰等特点。初步机理研究表明，CF 2 CO 2 Et 自由基的生成更容易与芳基的双键发生反应。
• 10.1021/acs.orglett.4c02792
  作者：Zhao, Xiaowei、Gao, Xiang、Zhao, Fangli、Wang, Lei、Zhang, Man、Zhou, Nengneng

  DOI：10.1021/acs.orglett.4c02792

  日期：——

  A copper-catalyzed trifluoromethylation of benzene-linked 1,7-dienes with 1-trifluoromethyl-1,2-benziodoxole via a radical cascade cyclization process for the synthesis of mono- and bis-trifluoromethylated benzoxepines is developed. The selectivity depends on substituents on the double bond of the allyl group in 1,7-dienes. The large-scale operation and late-stage functionalization of bioactive molecules

  开发了铜催化的苯连接的 1,7-二烯与 1-三氟甲基-1,2-苯并氧杂环戊烯通过自由基级联环化过程进行三氟甲基化，用于合成单三氟甲基化苯并氧杂环己烷。选择性取决于1,7-二烯中烯丙基双键上的取代基。生物活性分子的大规模操作和后期功能化揭示了该协议的有前景的实用性。
• Rhodium(III)-Catalyzed<i>ortho</i>Alkenylation of<i>N</i>-Phenoxyacetamides with<i>N</i>-Tosylhydrazones or Diazoesters through CH Activation
  作者：Fangdong Hu、Ying Xia、Fei Ye、Zhenxing Liu、Chen Ma、Yan Zhang、Jianbo Wang

  DOI：10.1002/anie.201309650

  日期：2014.1.27

  A coupling reaction of N‐phenoxyacetamides with N‐tosylhydrazones or diazoesters through RhIII‐catalyzed CH activation is reported. In this reaction, ortho‐alkenyl phenols were obtained in good yields and with excellent regio‐ and stereoselectivity. Rh–carbene migratory insertion is proposed as the key step in the reaction mechanism.

  的偶联反应Ñ -phenoxyacetamides与Ñ -tosylhydrazones或通过铑diazoesters III催化的Ç  H被报道活化。在该反应中，获得了高收率的邻链烯基苯酚，并且具有出色的区域选择性和立体选择性。Rh-卡宾迁移插入被认为是反应机理中的关键步骤。