2,6-diethylchlorobenzene

• 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: 2,6-diethylchlorobenzene
• 英文别名: 2-Chloro-1,3-diethylbenzene
• 化学式: C₁₀H₁₃Cl
• 分子量: 168.666
• InChiKey: METJMKLKGUXIGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,6-diethylchlorobenzene 在 甲醇 、 四次甲氨基乙硼烷 、 chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) 、 potassium acetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 22.08h， 生成 (2,6-diethylphenyl)boronic acid
  参考文献：
  名称：

  钯催化芳基和杂芳基卤化物使用四（二甲氨基）二硼硼化：一步更环保

  摘要：

  报道了钯催化芳基和杂芳基卤化物与新型硼酸化剂四（二甲氨基）二硼 [(Me 2 N) 2 B–B(NMe 2 ) 2 ] 的硼化反应。该方法是对先前报道的利用双硼酸 (BBA) 的方法的补充，因为某些底物在一组优化的反应条件下比另一组表现更好。由于四（二甲氨基）二硼是 BBA 和双（频哪醇）二硼（B 2 Pin 2）的合成前体，因此新方法代表了当前硼化方法的原子经济性和效率更高的方法。

  DOI：

  10.1021/ol302124j
• 作为产物：
  描述：

  2,6-二乙基苯胺 在 盐酸 、 sodium nitrite 、 copper(l) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 0.83h， 以46%的产率得到2,6-diethylchlorobenzene
  参考文献：
  名称：

  An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids

  摘要：

  An active, general, and long-lived palladium catalyst for Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups is reported. In reactions of arylbromide bearing two o-tert-butyl substituents, C(sp(3))-H arylation of the tert-butyl group, rather than the Suzuki-Miyaura reaction, proceeded in excellent yield. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

  DOI：

  10.1021/jo402089r

文献信息

• Ligand‐Facilitated Reductive Coupling of Benzyl Chlorides with Aryl Chlorides Catalyzed by Well‐Defined Heteroleptic Ni (II)‐NHC Complexes
  作者：Gusheng Lu、Ruipeng Li、Zhengwang Shen、Qinjia Wu、Hongmei Sun

  DOI：10.1002/aoc.5741

  日期：2020.9

  3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene), complex 1 exhibited superior catalytic activity in the magnesium‐mediated reductive coupling of benzyl chlorides with aryl chlorides, featuring outstanding tolerance of both coupling partners with steric demand. This study discloses a ligand‐facilitated reductive coupling of benzyl chlorides with aryl chlorides, which provides a new and practical synthetic

  新型杂合Ni（II）配合物，带有高度受阻但具有柔性的IPr *配体，Ni（IPr *）（PPh 3）Br 2（1）和Ni（IPr *）（PCy 3）Br 2（2）（IPr * = 1,3-双（2,6-双（二苯甲基）-4-甲基苯基）咪唑-2-亚基可以轻松制备，产率分别为78％和89％。两者均通过元素分析和NMR光谱进行了表征，并对1进行了X射线晶体学分析。与2及其类似物相比，其空间要求较低的IPr配体（IPr = 1,3-二（2,6-二异丙基苯基）咪唑-2-亚基）复杂1在苄基氯与芳基氯的镁介导的还原偶联中表现出卓越的催化活性，这两种偶联伙伴均具有出色的空间耐受性。这项研究揭示了苄基氯与芳基氯的配体促进还原偶联，为二芳基甲烷的合成提供了一种新的实用合成工具。
• Lubricating compositions containing ashless catalytic antioxidant additives
  申请人：Patil Abhimanyu O.

  公开号：US20070265178A1

  公开（公告）日：2007-11-15

  The invention comprises lubricating compositions and hydraulic fluids containing N,N′-diaryl-o-phenylenediamine compounds that impart good levels of oxidation inhibition in the lubricants and hydraulic fluids. The invention further comprises a method of making N,N′-diaryl-o-phenylenediamine compounds.

  本发明包括含有N,N′-二芳基-邻-苯二胺化合物的润滑组合物和液压油，这些化合物在润滑剂和液压油中提供了良好的氧化抑制作用。本发明还涉及一种制造N,N′-二芳基-邻-苯二胺化合物的方法。
• NHC-Pd(II)-azole complexes catalyzed Suzuki–Miyaura cross-coupling of sterically hindered aryl chlorides with arylboronic acids
  作者：Yingying Zhang、Rong Zhang、Chang Ni、Xue Zhang、Yanji Li、Qingwen Lu、Yuxuan Zhao、Fangwai Han、Yongfei Zeng、Guiyan Liu

  DOI：10.1016/j.tetlet.2019.151541

  日期：2020.3

  hindered biaryls efficiently, a series of NHC-Pd(II)-azole complexes bearing sterically hindered ligands were synthesized and characterized. The steric environment effect as well as the electronic effect of the azole ligands has been assessed. All these complexes were applied in the Suzuki−Miyaura cross-coupling reaction of sterically hindered aryl chlorides with low catalysts loadings (0.1 mol %) under

  为了有效地合成受阻联芳基，合成并表征了一系列带有空间受阻配体的NHC-Pd（II）-唑配合物。已经评估了空间环境效应以及唑配体的电子效应。所有这些络合物均在空气中温和条件下，以低催化剂负载量（0.1摩尔％）用于空间受阻芳基氯的Suzuki-Miyaura交叉偶联反应中，并获得良好至优异的空间受阻联芳基分离产率。
• Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls
  作者：Selçuk Çalimsiz、Mahmoud Sayah、Debasis Mallik、Michael G. Organ

  DOI：10.1002/anie.200906811

  日期：2010.3.8

  Cool couplings: Complex, hindered biaryls have been prepared at temperatures ranging from 0°C to room temperature, or with gentle heating. The Pd‐PEPPSI‐IPent catalyst (see scheme) nicely couples starting materials containing acidic moieties and routinely prepares biaryl derivatives where one or both rings comprising the biaryl are heterocyclic. Ar1=hindered aryl or heteroaryl, Ar2=unactivated aryl

  冷偶合：复杂的受阻联芳基已在0°C至室温的温度范围内或温和加热下制备。Pd-PEPPSI-IPent催化剂（参见方案）很好地偶联了含有酸性部分的原料，并常规制备了其中一个或两个包含联芳基的环为杂环的联芳基衍生物。Ar 1 =受阻的芳基或杂芳基，Ar 2 =未活化的芳基或杂芳基。
• Sterically Demanding, Bioxazoline-Derived N-Heterocyclic Carbene Ligands with Restricted Flexibility for Catalysis
  作者：Gereon Altenhoff、Richard Goddard、Christian W. Lehmann、Frank Glorius

  DOI：10.1021/ja045349r

  日期：2004.11.1

  A unique family of N-heterocyclic carbenes derived from bioxazolines (IBiox) suitable for application in transition-metal catalysis is described. The ligands are electron rich, sterically demanding, and have restricted flexibility. Their usefulness has been demonstrated in the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides and boronic acids. For the first time, tetraortho-substituted

  描述了从生物恶唑啉 (IBiox) 衍生的一个独特的 N-杂环卡宾家族，适用于过渡金属催化。配体富含电子，空间要求高，灵活性有限。它们的有用性已在空间位阻芳基氯化物和硼酸的 Suzuki-Miyaura 交叉偶联中得到证明。首次使用 Suzuki-Miyaura 方法从芳基氯合成了具有甲基和更大邻位取代基的四邻位取代联芳基化合物。