(2-(pyridin-2-yl)phenyl)(4-(trifluoromethyl)phenyl)methanol | 1312618-03-3

• 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: (2-(pyridin-2-yl)phenyl)(4-(trifluoromethyl)phenyl)methanol
• 英文别名: alpha-[4-(Trifluoromethyl)phenyl]-2-(2-pyridinyl)benzenemethanol；(2-pyridin-2-ylphenyl)-[4-(trifluoromethyl)phenyl]methanol
• CAS: 1312618-03-3
• 化学式: C₁₉H₁₄F₃NO
• 分子量: 329.321
• InChiKey: AAAUQXOKPUYJMO-UHFFFAOYSA-N

物化性质

• 沸点：
  462.5±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-(pyridin-2-yl)phenyl)(4-(trifluoromethyl)phenyl)methanol 在 silver hexafluoroantimonate 、 carbonyl(pentamethylcyclopentadienyl)cobalt diiodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以90%的产率得到2-苯基吡啶
  参考文献：
  名称：

  Cobalt(III)-Catalyzed Functionalization of Unstrained Carbon–Carbon Bonds through β-Carbon Cleavage of Alcohols

  摘要：

  We demonstrate that a simple Co(III)-complex can efficiently catalyze the cleavage of unstrained C-C bonds via the beta-carbon elimination of secondary and tertiary alcohols bearing a directing group. The cobalt-aryl intermediate generated under the reaction conditions can be trapped by different electrophiles to generate a new carbon carbon bond. Some essential features of this new Co-based mechanistic manifold were revealed by preliminary mechanistic studies.

  DOI：

  10.1021/acscatal.5b01753
• 作为产物：
  描述：

  (4-chlorophenyl)(2-(pyridin-2-yl)phenyl)methanol 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 氢气 、 palladium diacetate 作用下， 以 乙醚 、 乙醇 、 正己烷 、 乙腈 为溶剂， 反应 36.67h， 生成 (2-(pyridin-2-yl)phenyl)(4-(trifluoromethyl)phenyl)methanol
  参考文献：
  名称：

  作为C还原裂解？苄基仲醇的C键：含氮基团指导的铑催化

  摘要：

  切割松动：1,1- Biarylmethanol基板经历作为C还原裂解 C键在阳离子铑的存在III催化剂和H 2（参见方案; DG =引导组）。在反应系统中可以容忍各种官能团。初步研究表明，五元的rhodocycle中间体参与催化循环，然后将其转化为Rh III氢化物进行还原。

  DOI：

  10.1002/anie.201204338

文献信息

• Manganese-Catalyzed Direct Nucleophilic C(sp²)H Addition to Aldehydes and Nitriles
  作者：Bingwei Zhou、Yuanyuan Hu、Congyang Wang

  DOI：10.1002/anie.201506187

  日期：2015.11.9

  Herein, a manganese‐catalyzed nucleophilic addition of inert C(sp2)H bonds to aldehydes and nitriles is disclosed by virtue of a dual activation strategy. The reactions feature mild reaction conditions, excellent regio‐ and stereoselectivity, and a wide substrate scope, which includes both aromatic and olefinic CH bonds, as well as a large variety of aldehydes and nitriles. Moreover, mechanistic studies

  本文通过双重活化策略公开了锰催化的惰性C（sp 2）H键与醛和腈的亲核加成反应。该反应具有温和的反应条件，出色的区域选择性和立体选择性以及广泛的底物范围，其中包括芳族和烯烃的CH键以及各种醛和腈。此外，机理研究揭示了可能的催化循环。
• Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C–H Activation
  作者：Guo-Fu Zhang、Yue Li、Xiao-Qiang Xie、Cheng-Rong Ding

  DOI：10.1021/acs.orglett.7b00183

  日期：2017.3.3

  An efficient and direct ruthenium-catalyzed regioselective hydroxymethylation of (hetero)arenes via C-H activation with paraformaldehyde as a hydroxymethylating reagent is described. The corresponding products can be obtained in good to excellent yield. A number of aryl aldehydes can also be used in place of paraformaldehyde giving the desired alcohol products with similarly good results.

  描述了通过用低聚甲醛作为羟甲基化试剂的CH活化，有效和直接的钌催化（杂）芳烃的区域选择性羟甲基化。可以以良好至优异的产率获得相应的产物。也可以使用许多芳基醛代替多聚甲醛，得到所需的醇产物，并具有相似的良好结果。
• Rhodium(III)‐Catalyzed Aryl Borrowing Amination of Diaryl Methanols Containing Pyridine‐Directing Groups
  作者：Zheng‐Qiang Liu、Jing Tao、Xin Zhuang、Chuan‐Ming Hong、Zhen Luo、Yu‐Fei Wu、Qing‐Hua Li、Tang‐Lin Liu

  DOI：10.1002/adsc.202100772

  日期：2021.12.7

  The rhodium(III)-catalyzed aryl borrowing amination of various diaryl methanols with sulfonamides have been developed. The amination of alcohols via C−C bond activation is less developed and remains a challenge. These aryl borrowing reactions feature mild reaction conditions, good functional group tolerance, and compatibility with a wide range of alcohols, overall comprising an atom- and step-economic

  已经开发了铑 (III) 催化的各种二芳基甲醇与磺酰胺的借芳基胺化反应。通过 C-C 键活化对醇进行胺化作用尚不成熟，仍然是一个挑战。这些芳基借用反应具有反应条件温和、官能团耐受性好、与多种醇类相容性好等特点，总体上是一个原子经济和步骤经济的过程。机理研究表明，在芳基借用胺化反应过程中存在红环络合物。
• Grignard-Type Arylation of Aldehydes via a Rhodium-Catalyzed CH Activation under Mild Conditions
  作者：Luo Yang、Camille A. Correia、Chao-Jun Li

  DOI：10.1002/adsc.201100232

  日期：2011.5

  An efficient Grignard‐type arylation of aldehydes via aryl CH activation was achieved under mild conditions catalyzed by rhodium. The reaction provides an easy access to a wide variety of benzyl alcohols and can tolerate various functional groups as well as air and water.

  在铑催化的温和条件下，可以通过芳基CH活化实现醛的有效格氏（Grignard）型芳基化反应。该反应提供了容易获得各种苄醇的途径，并且可以耐受各种官能团以及空气和水。
• Dimeric Manganese-Catalyzed Direct Nucleophilic Addition of C(sp²)–H Bonds to Inert Aldehydes
  作者：Hongxin Liu、Junqin Peng、Bin Li、Baiquan Wang

  DOI：10.1021/acs.joc.2c01908

  日期：2022.11.4

  An efficient direct nucleophilic addition reaction of C(sp2)–H bonds to aldehydes catalyzed by a dimeric manganese has been developed. This reaction has a broad range of substrates, and high yields were also obtained with inert aliphatic aldehydes as substrates. A dimeric Mn2(CO)8Br2 was proven to be a more efficient catalyst precursor than the monomeric Mn(CO)5Br.

  已经开发了由二聚锰催化的 C(sp 2 )-H 键与醛的有效直接亲核加成反应。该反应具有广泛的底物范围，并且以惰性脂肪醛作为底物也获得了高产率。二聚体Mn 2 (CO) 8 Br 2被证明是比单体Mn(CO) 5 Br 更有效的催化剂前体。