| 1580514-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1580514-93-7
• 化学式: C₉H₇BF₃*K
• 分子量: 222.059
• InChiKey: ZRNPWUVTFOMUBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-苯基3,6-二氢-2H-吡喃 、 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以88%的产率得到4-phenyl-6-(m-tolylethynyl)-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Oxidative C H alkynylation of 3,6-dihydro-2H-pyrans

  摘要：

  Current synthesis of alpha-substituted 3,6-dihydro-2H-pyrans dominantly relies on functional group transformation. Herein, a direct and practical oxidative C-H alkynylation and alkenylation of 3,6-dihydro-2H-pyran skeletons with a range of potassium trifluoroborates is developed. The metal-free process is well tolerated with a wide variety of 3,6-dihydro-2H-pyrans, rapidly providing a library of 2,4-disubstituted 3,6-dihydro-2H-pyrans with diverse patterns of alpha-functionalities for further diversification and bioactive small molecule identification. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.03.027
• 作为产物：
  描述：

  硼酸三甲酯 、 3-甲基苯乙炔 在 正丁基锂 、 二氟化氢钾 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.0h， 以72%的产率得到
  参考文献：
  名称：

  Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent

  摘要：

  Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.005

文献信息

• Diastereoselectively Complementary C–H Functionalization Enables Access to Structurally and Stereochemically Diverse 2,6-Substituted Piperidines
  作者：Gang Wang、Ying Mao、Lei Liu

  DOI：10.1021/acs.orglett.6b03372

  日期：2016.12.16

  The preparation of 2,6-substituted piperidine derivatives through diastereoselective C–H functionalization of corresponding nitrogen heterocycles represents an appealing protocol and yet remains a formidable challenge. Here, we describe a stereochemically complementary oxidative C–H functionalization of N-carbamoyl tetrahydropyridines with a wide variety of building blocks, providing either the cis-

  通过相应的氮杂环的非对映选择性CH官能团制备2，6-取代的哌啶衍生物是一个有吸引力的方案，但仍然是一个艰巨的挑战。在这里，我们描述了N-氨基甲酰基四氢吡啶的立体化学互补氧化C–H功能化，具有多种结构单元，可为顺式-或反式-2,6-取代的哌啶提供多种功能模式。不含金属的温和工艺具有极佳的区域选择性和非对映选择性，以及对官能团的耐受性。还描述了天然产物和类似物合成中的合成用途。
• Practical and Highly Selective CH Functionalization of Structurally Diverse Ethers
  作者：Miao Wan、Zhilin Meng、Hongxiang Lou、Lei Liu

  DOI：10.1002/anie.201407083

  日期：2014.12.8

  A trityl ion mediated CH functionalization of ethers with a wide range of nucleophiles at ambient temperature has been developed. The reaction displays high chemoselectivity and good functional group tolerance. The protocol also exhibits excellent regio‐ and diastereoselectivities for the unsymmetric ethers, thus stereoselectively generating highly functionalized disubstituted 2,5‐trans tetrahydrofurans

  在环境温度下，已开发出由三苯甲基离子介导的具有多种亲核试剂的醚的CH功能化。该反应显示出高的化学选择性和良好的官能团耐受性。该协议还对非对称醚表现出出色的区域选择性和非对映选择性，因此立体选择性地生成高度官能化的二取代的2,5-反式四氢呋喃（THF），2,6-反式四氢吡喃（THP），2,6-反式二氢吡喃（DHP），和1,3-反式异色团，并突出了该协议在复杂分子合成中的能力。
• Direct oxidative dearomatization of indoles: access to structurally diverse 2,2-disubstituted indolin-3-ones
  作者：Xigong Liu、Xue Yan、Yingde Tang、Cheng-Shi Jiang、Jin-Hai Yu、Kaiming Wang、Hua Zhang

  DOI：10.1039/c9cc02956g

  日期：——

  Described is an efficient oxidative dearomatization of indoles with TEMPO oxoammonium salt and a broad range of nucleophiles. Under very mild conditions, dearomative oxyalkynylation and oxyalkenylation of indoles to structurally diverse 2,2-disubstituted indolin-3-ones were developed for the first time with high atom-economy. In addition, dearomative oxyarylation, oxyallylation, and oxycyanation of

  描述了用TEMPO氧铵盐和多种亲核试剂对吲哚进行有效的氧化脱芳香化作用。在非常温和的条件下，首次以高原子经济性将吲哚的脱芳基氧基炔基化和羟基烯基化为结构上不同的2,2-二取代的吲哚-3-酮。另外，还证明了吲哚的脱芳香族的氧化芳基化，氧化烯丙基化和氧化氰化。机理研究表明，TEMPO氧铵盐是通过电子给体-受体（EDA）中间体的唯一氧化剂。
• Copper(II) Triflate-Catalyzed Aerobic Oxidative CH Functionalization of Glycine Derivatives with Olefins and Organoboranes
  作者：Zhiyu Xie、Jiong Jia、Xigong Liu、Lei Liu

  DOI：10.1002/adsc.201501015

  日期：2016.3.17

  triflate‐catalyzed aerobic oxidative CH functionalization of glycine derivatives with olefins and organoboranes has been established. The mild reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both glycine derivatives and the two types of nucleophilic components, allowing for the facile synthesis of diverse substituted quinolines and glycine derivatives bearing

  建立了经济实用的三氟甲磺酸铜（II）催化甘氨酸衍生物与烯烃和有机硼烷的好氧氧化CH功能化。温和的反应具有优异的官能团耐受性，并且在甘氨酸衍生物和两种类型的亲核组分方面均显示出广阔的范围，从而可以轻松合成各种取代的喹啉和甘氨酸衍生物，这些衍生物在α-中具有各种功能模式位置。
• Oxidative C–H functionalization of N-carbamoyl 1,2-dihydroquinolines
  作者：Ziqiang Liu、Lei Chen、Jing Li、Ke Liu、Jiaqi Zhao、Mengmeng Xu、Lei Feng、Ren-zhong Wan、Wei Li、Lei Liu

  DOI：10.1039/c7ob01793f

  日期：——

  A modular and efficient method for the synthesis of α-substituted 1,2-dihydroquinolines is described. Under mild metal-free conditions, readily available N-carbamoyl 1,2-dihydroquinolines undergo oxidative C–H alkynylation, alkenylation, and allylation with a range of potassium trifluoroborates using TEMPO oxoammonium salt as an oxidant.

  描述了用于合成α-取代的1，2-二氢喹啉的模块化且有效的方法。在温和的不含金属的条件下，使用TEMPO氧铵盐作为氧化剂，容易获得的N-氨基甲酰基1,2-二氢喹啉会与一系列三氟硼酸钾进行氧化性C–H炔基化，烯基化和烯丙基化。