(E)-2-(1-phenylprop-1-en-1-yl)phenol | 39477-88-8

• 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: (E)-2-(1-phenylprop-1-en-1-yl)phenol
• 英文别名: 2-(1-phenyl-1-propen-1-yl)phenol；2-[(E)-1-phenylprop-1-enyl]phenol
• CAS: 39477-88-8
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: VNIBUMSDDCXJGZ-XNJYKOPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯丙酮 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 (E)-2-(1-phenylprop-1-en-1-yl)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

• Synthesis of Polyaryl-Substituted Olefins via a Rh(III)-Catalyzed One-Pot Reaction Using <i>N</i>-Phenoxyacetamides, Ketones, and Hydrazines
  作者：Yan Zhang、Yu He、Lisha Li、Mingming Ji、Xiao-Zong Li、Gangguo Zhu

  DOI：10.1021/acs.joc.8b00108

  日期：2018.3.2

  A Rh(III)-catalyzed one-pot reaction of N-phenoxyacetamides, ketones, and hydrazines for a facile access to disubstituted and trisubstituted ethylenes is reported. In this method, various ketones are transformed into donor–donor diazo compounds, which engage in insertion with N-phenoxyacetamides, following β-H elimination under Rh(III) catalysis to generate (E)-polyaryl-substituted olefins. This chemistry

  报道了Rh（III）催化的N-苯氧基乙酰胺，酮和肼的一锅反应，可轻松获得二取代和三取代的乙烯。在这种方法中，将多种酮转化为供体-供体重氮化合物，在Rh（III）催化下将β-H消除后，可与N-苯氧基乙酰胺插入以生成（E）-聚芳基取代的烯烃。这种化学物质具有简单的原料，温和的反应条件和良好的官能团耐受性。
• Mechanistic Insights into Rhenium‐Catalyzed Regioselective C‐Alkenylation of Phenols with Internal Alkynes
  作者：Masahito Murai、Masaki Yamamoto、Kazuhiko Takai

  DOI：10.1002/chem.201903910

  日期：2019.11.27

  rhenium, a metal between the early and late transition metals in the periodic table, was key for the activation of both the soft carbon-carbon triple bond of the alkyne and the hard oxygen atom of the phenol, at the same time. ortho-Selective alkenylation with allenes also provided the corresponding adducts with a substitution pattern different from that obtained by the addition reaction with alkynes.

  分离出（μ-芳基氧代）complex络合物，并确认其为rh与炔烃催化with保护的未保护酚的邻链烯基化（C-烯基化）的关键预催化剂。该反应仅提供了邻烯基苯酚。没有观察到对或多烯基化酚的形成和加氢苯氧基化（O-烯基化）产物。几个机理实验排除了经典的Friedel-Crafts型机理，从而导致提出的酚羟基辅助的亲电烯基化是最合理的反应机理。为此，在周期表中使用，（一种在元素周期表中早期和晚期过渡金属之间的金属）是激活炔烃的软碳-碳三键和苯酚的硬氧原子的关键。同一时间。
• Rhenium-Catalyzed Regioselective <i>ortho</i>-Alkenylation and [3 + 2 + 1] Cycloaddition of Phenols with Internal Alkynes
  作者：Masahito Murai、Masaki Yamamoto、Kazuhiko Takai

  DOI：10.1021/acs.orglett.9b01214

  日期：2019.5.3

  (C-alkenylation) of unprotected phenols with alkynes was developed. The protocol provided ortho-alkenylphenols exclusively, and formation of para- or multiply alkenylated phenols and hydrophenoxylation (O-alkenylation) products were not observed. The [3 + 2 + 1] cycloaddition of phenols and two alkynes via ortho-alkenylation was also demonstrated, in which the alkynes functioned as both two- and one-carbon

  开发了一种操作简单且直接的炔烃。保护的未保护酚的or催化的邻链烯基化（C链烯基化）。该协议提供邻-alkenylphenols排他地，和形成对位-或乘法烯化的酚类和hydrophenoxylation（ö -alkenylation）没有观察到产物。还证明了通过邻链烯基化作用的苯酚和两个炔烃的[3 + 2 +1]环加成反应，其中炔烃同时具有2个碳原子单位和1个碳原子单位。这些反应使用容易获得的起始原料在中性条件下进行，没有其他配体。
• Highly Enantioselective Hydrogenation of Styrenes Directed by 2′-Hydroxyl Groups
  作者：Xiang Wang、Anil Guram、Seb Caille、Jack Hu、J P. Preston、Michael Ronk、Shawn Walker

  DOI：10.1021/ol200422p

  日期：2011.4.1

  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.
• CASIRAGHI G.; CASNDTI G.; SARTORI G.; BOLZONI L., J. CHEM. SOC. PERKIN TRANS., 1979, PART 1, NO 8, 2027-2029
  作者：CASIRAGHI G.、 CASNDTI G.、 SARTORI G.、 BOLZONI L.

  DOI：——

  日期：——