3-phenyl-2-(4-(trifluoromethyl)phenyl)propanenitrile

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-phenyl-2-(4-(trifluoromethyl)phenyl)propanenitrile
• 英文别名: 3-Phenyl-2-[4-(trifluoromethyl)phenyl]propanenitrile
• 化学式: C₁₆H₁₂F₃N
• 分子量: 275.273
• InChiKey: ITMJQAZNVDGFKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenyl-2-(4-(trifluoromethyl)phenyl)propanenitrile 在 硼烷四氢呋喃络合物 作用下， 生成
  参考文献：
  名称：

  Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1

  摘要：

  We report on a series of alpha-substituted-beta-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.036
• 作为产物：
  描述：

  3-phenyl-2-(4-(trifluoromethyl)phenyl)acrylonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3-phenyl-2-(4-(trifluoromethyl)phenyl)propanenitrile
  参考文献：
  名称：

  Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1

  摘要：

  We report on a series of alpha-substituted-beta-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.036

文献信息

• Enantioselective Rhodium-Catalyzed Allylic Substitution with a Nitrile Anion: Construction of Acyclic Quaternary Carbon Stereogenic Centers
  作者：Ben W. H. Turnbull、P. Andrew Evans

  DOI：10.1021/jacs.5b02810

  日期：2015.5.20

  A direct and highly enantioselective rhodium-catalyzed allylic alkylation of allyl benzoate with α-substituted benzyl nitrile pronucleophiles is described. This simple protocol provides a new approach toward the synthesis of acyclic quaternary carbon stereogenic centers and provides the first example of the direct asymmetric alkylation of a nitrile anion. The synthetic utility of the nitrile products

  描述了直接和高度对映选择性铑催化的苯甲酸烯丙酯烯丙基烷基化与 α-取代的苄基腈亲核试剂。这个简单的协议提供了一种合成无环季碳立体中心的新方法，并提供了腈阴离子直接不对称烷基化的第一个例子。腈产品的合成效用通过转化为各种官能团和以快速的四步序列合成生物活性芳基哌嗪得到充分证明。
• Copper-catalyzed radical oxidative C(sp3)–H/C(sp3)–H cross-coupling between arylacetonitriles and benzylic compounds
  作者：Jing Xiao、Fangshao Li、Ting Zhong、Xiaofang Wu、Fengzhe Guo、Qiang Li、Zi-Long Tang

  DOI：10.1016/j.tet.2020.131621

  日期：2020.11

  For the first time, a novel copper-catalyzed direct C(sp3)–H/C(sp3)–H cross-coupling of arylacetonitriles with unactivated benzylic compounds was described, allowing various a-benzylated arylacetonitriles to be readily accessible under base-free conditions. Mechanistic investigations suggested that the reaction proceeds through radical process and the C(sp3)–H cleavage of arylacetonitriles probably

  首次描述了一种新颖的铜催化芳基乙腈与未活化的苄基化合物的直接C（sp 3）–H / C（sp 3）–H交叉偶联的方法，使各种α-苄基化的芳基乙腈可以在碱下容易地获得无条件。机理研究表明，反应是通过自由基过程进行的，芳基乙腈的C（sp 3）-H裂解可能是决定速率的步骤。
• Bioinspired Metal‐Free Formal Decarbonylation of α‐Branched Aliphatic Aldehydes at Ambient Temperature
  作者：Sven C. Richter、Martin Oestreich

  DOI：10.1002/chem.201902082

  日期：2019.6.26

  secondary aliphatic aldehydes. The new methodology mimics the biosynthetic decarbonylation pathway through oxidative C−C bond cleavage rather than the C(O)−H bond activation known from conventional Tsuji–Wilkinson‐type reactions. The substrate scope is complementary to existing transition‐metal‐catalyzed protocols.

  通过一系列的Baeyer-Villiger氧化和Lewis酸促进的Et 3 SiH甲酸还原反应，可实现叔和仲脂族醛的无金属正式脱羰作用。这种新方法模仿了传统的Tsuji-Wilkinson型反应中已知的通过氧化C-C键裂解而不是C（O）-H键活化的生物合成脱羰途径。底物范围是对现有过渡金属催化方案的补充。
• Development of an imidazole-based <i>N</i>,<i>N</i>-bidentate ligand for the manganese catalyzed direct coupling of nitriles with alcohols
  作者：Qian Tang、Dingguo Song、Kali Zhang、Wenhao Mao、Xianghua Zhao、Ding Du、Fei Ling、Weihui Zhong

  DOI：10.1039/d4ra00817k

  日期：2024.4.22

  environmentally friendly approaches for the direct coupling of alcohols with nitriles to assemble various important branched nitriles. The development of simple and efficient ligands is a crucial issue in this field. In this study, we designed a series of readily available N,N-bidentate ligands that demonstrated good efficiency in the Mn-catalyzed BH reaction of alcohols and nitrile derivatives, yielding the targeted

  3d-金属催化的借氢 (BH) 反应代表了醇与腈直接偶联以组装各种重要的支链腈的强大且环保的方法。开发简单有效的配体是该领域的一个关键问题。在这项研究中，我们设计了一系列容易获得的N ， N-二齿配体，这些配体在Mn催化的醇和腈衍生物的BH反应中表现出良好的效率，以中等至良好的产率产生目标腈。值得注意的是，通过两级联借氢程序成功合成阿尼帕米进一步证明了该方案的温和性和实用性。
• Efficient Solvent-Free Selective Monoalkylation of Arylacetonitriles with Mono-, Bis-, and Tris-primary Alcohols Catalyzed by a Cp*Ir Complex
  作者：Christian Löfberg、Ronald Grigg、Mark A. Whittaker、Ann Keep、Andrew Derrick

  DOI：10.1021/jo061113p

  日期：2006.10.1

  Our objectives were to develop catalytic atom-economic processes accessing and/or incorporating versatile functionality using aryl/heteroaryl acetonitriles as substrates. We report essentially solvent-free [Cp*IrCl2](2) catalyzed redox neutral processes whereby substituted acetonitriles react with primary alcohols to deliver monosubstituted aryl/heteroaryl acetonitriles in excellent yield. We further demonstrate that such processes can be achieved by conventional or microwave heating and that bis- and tris-primary alcohols are also processed efficiently.