(E)-1-(2-cyclohexylvinyl)-3-fluorobenzene

• 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)-1-(2-cyclohexylvinyl)-3-fluorobenzene
• 英文别名: 1-[(E)-2-cyclohexylethenyl]-3-fluorobenzene
• 化学式: C₁₄H₁₇F
• 分子量: 204.287
• InChiKey: LXOHNODRKOQCTA-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-氟肉桂酸 、 环己烷 在 iron(III)-acetylacetonate 、 二叔丁基过氧化物 作用下， 反应 24.0h， 以88%的产率得到(E)-1-(2-cyclohexylvinyl)-3-fluorobenzene
  参考文献：
  名称：

  铁催化的环烷烃与芳基乙烯基羧酸通过自由基过程脱羧烯基化。

  摘要：

  Fe(acac)3 催化的 2-(芳基)乙烯基羧酸与环烷烃的脱羧偶联是通过使用 DTBP 作为氧化剂通过自由基过程开发的。该反应可耐受多种底物，并且以良好至极好的产率 (71-95%) 获得产物。该反应还显示出优异的立体选择性，并且仅获得反式异构体。

  DOI：

  10.3762/bjoc.9.197

文献信息

• Photoinduced copper-catalyzed dual decarboxylative coupling of α,β-unsaturated carboxylic acids with redox-active esters
  作者：Xiao-Yu Lu、Ang Gao、Qi-Le Liu、Ze-Jie Xia

  DOI：10.1016/j.tet.2021.132259

  日期：2021.7

  The first photoinduced copper-catalyzed dual decarboxylative cross-coupling of α,β-unsaturated carboxylic acids and redox-active esters has been developed. This reaction enabled C(sp2)–C(sp3) bond formation, which afforded a variety of synthetically valuable alkene derivatives. Many α,β-unsaturated carboxylic acids and redox-active ester derivatives were tolerant to this reaction. The reaction also

  已经开发出第一个光诱导铜催化的 α,β-不饱和羧酸和氧化还原活性酯的双脱羧交叉偶联。该反应使 C( sp 2 )–C( sp 3 ) 键形成成为可能，从而提供了多种具有合成价值的烯烃衍生物。许多 α,β-不饱和羧酸和具有氧化还原活性的酯衍生物都耐受该反应。该反应还耐受许多常见的官能团。
• Thiophene-Alkyne-Based CMPs as Highly Selective Regulators for Oxidative Heck Reaction
  作者：Ren-Hao Li、Zong-Cang Ding、Cun-Yao Li、Jun-Jia Chen、Yun-Bing Zhou、Xiao-Ming An、Yun-Jie Ding、Zhuang-Ping Zhan

  DOI：10.1021/acs.orglett.7b01858

  日期：2017.9.1

  as ligands for PdII-promoted organic reactions are reported for the first time. These ligands were utilized as catalytic sites and integrated into the skeleton of conjugated microporous polymers. By employing these CMP materials as selective regulators, oxidative Heck reactions between arylboronic esters and electronically unbiased alkenes provide highly selective linear products.

  首次报道了含有相邻的C≡C基团作为Pd II促进的有机反应的配体的噻吩。这些配体被用作催化位点并整合到共轭微孔聚合物的骨架中。通过将这些CMP材料用作选择性调节剂，芳基硼酸酯与电子无偏烯烃之间的氧化Heck反应可提供高度选择性的线性产物。
• Conjugated Microporous Polymer as Heterogeneous Ligand for Highly Selective Oxidative Heck Reaction
  作者：Yun-Bing Zhou、Yu-Qing Wang、Li-Chao Ning、Zong-Cang Ding、Wen-Long Wang、Cheng-Ke Ding、Ren-Hao Li、Jun-Jia Chen、Xin Lu、Yun-Jie Ding、Zhuang-Ping Zhan

  DOI：10.1021/jacs.7b00643

  日期：2017.3.22

  catalytic ligand for the PdII-catalyzed oxidative Heck reaction with high linear selectivity. The linear selectivity of CMP-1 is about 30 times higher than that of bipyridine-based monomer ligand. This work opens a new front of using CMP as an intriguing platform for developing highly efficient catalysts in controlling the regioselectivity in organic reactions.

  设计并合成了一系列含有 C≡C 键的吡啶型配体用于选择性氧化 Heck 反应。这些配体被用作功能单元并整合到共轭微孔聚合物的骨架中。6,6'-二碘-2,2'-联吡啶和1,3,5-三乙炔苯通过Sonogashira交叉偶联策略缩聚得到CMP-1材料。所得的 CMP-1 用作 PdII 催化的氧化 Heck 反应的多相催化配体，具有高线性选择性。CMP-1 的线性选择性比基于联吡啶的单体配体高约 30 倍。这项工作开辟了使用 CMP 作为开发高效催化剂控制有机反应区域选择性的有趣平台的新前沿。
• Photoinduced Deaminative Coupling of Alkylpyridium Salts with Terminal Arylalkynes
  作者：Shu-Zhen Lai、Yu-Ming Yang、Hai Xu、Zhen-Yu Tang、Zhuangzhu Luo

  DOI：10.1021/acs.joc.0c01928

  日期：2020.12.4

  A novel and simple Z-alkene synthesis by the photocatalyzed coupling reactions of alkylpyridium salts, which were prepared from primary amines, with terminal aryl alkynes at room temperature is reported here. A wide range of primary amines, which contain different functional groups, were tolerated under these conditions. The mild reaction conditions, broad substrate scope, functional group tolerance

  本文报道了在室温下由伯胺制得的烷基吡啶鎓盐与末端芳基炔烃的光催化偶合反应新型新颖的Z-烯烃合成方法。在这些条件下可以耐受多种包含不同官能团的伯胺。温和的反应条件，宽泛的底物范围，官能团耐受性和操作简便性使该脱氨基偶联反应成为有机合成中的重要方法。
• Paired Oxidative and Reductive Catalysis: Breaking the Potential Barrier of Electrochemical C(sp³)−H Alkenylation**
  作者：Long Zou、Xiaofan Wang、Siqi Xiang、Weipeng Zheng、Qingquan Lu

  DOI：10.1002/anie.202301026

  日期：2023.6.12

  Due to the intrinsic inertness of alkanes, strong oxidative conditions are typically required to enable their C(sp³)−H functionalization. Herein, a paired electrocatalysis strategy was developed by integrating oxidative catalysis with reductive catalysis in one cell without interference, in which earth‐abundant iron and nickel are employed as the anodic and cathodic catalysts, respectively. This approach lowers the previously high oxidation potential required for alkane activation, enabling electrochemical alkane functionalization at the ultra‐low oxidation potential of ≈0.25 V vs. Ag/AgCl under mild conditions. Structurally diverse alkenes, including challenging all‐carbon tetrasubstituted olefins, can be accessed using readily available alkenyl electrophiles.

  摘要由于烷烃的内在惰性，通常需要在强氧化条件下才能实现其 C(sp3)-H 功能化。在此，我们开发了一种成对电催化策略，将氧化催化与还原催化无干扰地集成在一个电池中，其中采用了富含地球的铁和镍分别作为阳极和阴极催化剂。这种方法降低了以往烷烃活化所需的高氧化电位，在温和的条件下，以相对于 Ag/AgCl ≈0.25 V 的超低氧化电位实现了电化学烷烃官能化。利用容易获得的烯基亲电体，可以获得结构多样的烯烃，包括具有挑战性的全碳四取代烯烃。