5,5'-二氯-2,2'-联吡啶 | 100846-27-3

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5,5'-二氯-2,2'-联吡啶
• 英文名称: 5,5'-dichloro-2,2'-bipyridine
• 英文别名: 5-chloro-2-(5-chloropyridin-2-yl)pyridine
• CAS: 100846-27-3
• 化学式: C₁₀H₆Cl₂N₂
• 分子量: 225.077
• InChiKey: HYCKHRIFJYTAEM-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  320.6±37.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5'-二氯-2,2'-联吡啶 在 双氧水 、 三氟乙酸 作用下， 反应 3.0h， 生成 5,5'-dichloro-[2,2'-bipyridine] 1-oxide
  参考文献：
  名称：

  铑（III）通过双C–H键活化催化2,2'-联吡啶N-氧化物与炔烃的氧化环化

  摘要：

  已经开发了Rh（III）通过双C–H键活化与内部炔烃催化的2,2'-联吡啶N-氧化物的可转换环。调节反应条件使反应路径可以在翻转和非翻转环空之间切换，从而提供5,6-二取代的-1,10-菲咯啉和5,6,7,8-四取代的-1-（吡啶-2-基）异喹啉分别以高收率获得2-氧化物。该程序具有出色的区域选择性，广泛的底物范围和对官能团的高度耐受性。在催化反应中证明了这些获得的产物的合成效用。

  DOI：

  10.1021/acs.orglett.8b01434
• 作为产物：
  描述：

  3-氯吡啶 在 Ni(NO₃)₂-Ce(NO₃)₃-La(NO₃)₃-Mn(NO₃)_2-impregnated solid catalyst 作用下， 以 乙醇 为溶剂， 300.0 ℃ 、2.38 MPa 条件下， 生成 5,5'-二氯-2,2'-联吡啶
  参考文献：
  名称：

  一种2,2’-联吡啶及其衍生物的制备方法

  摘要：

  本发明公开了一种2,2’‑联吡啶及其衍生物的制备方法，该方法以式Ⅰ所示的吡啶或其衍生物为原料，在添加剂存在的情况下，在负载型催化剂作用下脱氢偶联生成式Ⅱ所示的2,2’‑联吡啶；其中，R为H、C1‑C2烷基、Cl、Br。本发明方法原料适用性广，原子利用率高、催化剂活性高、寿命长、副产少。

  公开号：

  CN107935919B

文献信息

• Isomer Dependence of Efficiency and Charge Recombination in Dye‐Sensitized Solar Cells Using Ru Complex Dyes Bearing Halogen Substituents
  作者：Nina Chadwick、D. Kishore Kumar、Aruna Ivaturi、Benjamin A. Grew、Hari M. Upadhyaya、Lesley J. Yellowlees、Neil Robertson

  DOI：10.1002/ejic.201500633

  日期：2015.10

  We have synthesised Ru(H2-dcbpy)(N,N′-Y2-bpy)(NCS)2 dyes (where N = 4, 5; Y = F, Cl, Br; N is the position on the bipyridyl ring where the halogen substituent is located) for dye-sensitised solar cells. We show that careful consideration of the position of the substituent, in conjunction with the nature of the substituents, on a bpy ring is important to optimize the solar cells performance. Changing

  我们已经合成了 Ru(H2-dcbpy)(N,N'-Y2-bpy)(NCS)2 染料（其中 N = 4, 5；Y = F、Cl、Br；N 是联吡啶环上的位置，其中卤素取代基位于）用于染料敏化太阳能电池。我们表明，仔细考虑取代基的位置，结合取代基的性质，在 bpy 环上对优化太阳能电池性能很重要。观察到改变位置（从 4,4' 到 5,5'）以及卤素（F、Cl 或 Br）取代基的性质会导致染料的电子和光谱性质发生变化，并影响染料的TiO2-染料-I-/I3-界面的复合率影响DSSCs中染料的性能。
• METHOD FOR MANUFACTURING CONJUGATED AROMATIC COMPOUND
  申请人：Oda Seiji

  公开号：US20110275859A1

  公开（公告）日：2011-11-10

  A method for manufacturing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (A) does not have (c1) a group represented by the following formula (10): wherein A 1 represents a C1-C20 alkoxy group etc.; (g1) a C1-C20 alkyl group which may be substituted with a fluorine atom etc.; and (h1) a C2-C20 acyl group which may be substituted with a fluorine atom etc., at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) wherein the aromatic compound (B) is structurally different from the above-mentioned aromatic compound (A), one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (B) does not have the above-mentioned (c1), (g1) and (h1) at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, in the presence of (i) a nickel compound, (ii) a metal reducing agent, (iii) at least one ligand (L1) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-withdrawing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-withdrawing group and having no substituent at 2- and 9-positions, and (iv) at least one ligand (L2) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-releasing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-releasing group and having no substituent at 2- and 9-positions.

  一种制备共轭芳香化合物的方法，包括将含有一个或两个离去基团的芳香化合物（A）与含有相同结构的上述芳香化合物（A）或结构不同的芳香化合物（B）反应，其中这些离去基团选自碘原子、溴原子和氯原子，与芳香环结合，而芳香化合物（A）没有以下式（10）所代表的基团：其中A1代表C1-C20烷氧基等；（g1）代表C1-C20烷基基团，可能被氟原子等取代；以及（h1）代表C2-C20酰基基团，可能被氟原子等取代，与离去基团结合的碳原子的相邻碳原子处没有上述（c1）、（g1）和（h1），在（i）镍化合物、（ii）金属还原剂、（iii）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L1），具有至少一个吸电子基团且在3-、6-、3′-和6′-位置没有取代基，以及（iv）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L2），具有至少一个释电子基团且在3-、6-、3′-和6′-位置没有取代基团的情况下，在上述离去基团结合的碳原子的相邻碳原子处进行反应。
• A study on the BF3 directed lithiation of 3-chloro- and 3-bromopyridine
  作者：Jaspreet S. Dhau、Amritpal Singh、Yoganjaneyulu Kasetti、Sonam Bhatia、Parsad V. Bharatam、Paula Brandão、Vítor Félix、Kamal N. Singh

  DOI：10.1016/j.tet.2013.10.026

  日期：2013.12

  The BF3-directed lithiation of 3-chloro- and 3-bromopyridine (1a and 1b, respectively) has been investigated. The reactions of 3-chloro- or 3-bromopyridine–BF3 adduct with LDA (1.3/1.1 equiv) followed by quenching with benzaldehyde or iodine exclusively gave the C-2 substituted products. However, when 2.2 equiv of LDA and dimethyl disulfide was used, a C-6 substituted product was obtained. Dilithiation

  研究了3-氯吡啶和3-溴吡啶的BF 3定向锂化（分别为1a和1b）。3-氯或3-溴吡啶-BF 3加合物与LDA（1.3 / 1.1当量）的反应，然后用苯甲醛或碘淬灭，仅得到C-2取代的产物。然而，当使用2.2当量的LDA和二甲基二硫化物时，获得了C-6取代的产物。在有和没有BF 3络合的情况下，已经研究了1a和1b的双锂化。Li⋯F（BF 3）相互作用的作用已通过实验和DFT计算进行了研究。
• 2,2' -BIPYRIDINE DERIVATIVE HAVING A REACTIVE SILYL GROUP, ITS PRODUCTION METHOD, AND TRANSITION METAL COMPLEX
  申请人：Ito Yusuke

  公开号：US20090299068A1

  公开（公告）日：2009-12-03

  A 2,2′-bipyridine derivative having a reactive silyl group represented by the following general formula (1): wherein R 1 and R 2 represent a substituent selected from a monovalent hydrocarbon group, an organoxy group, an acyloxy group, hydroxy group, a halogen atom, hydrogen atom, mercapto group, an amino group, cyano group, cyanate group, isocyanate group, thiocyanate group, and isothiocyanate group; R 3 represents a monovalent aliphatic unsaturated hydrocarbon group, an organoxy group, an alkoxy group, an acyloxy group, hydroxy group, a halogen atom, hydrogen atom, mercapto group, an amino group, cyano group, cyanate group, isocyanate group, thiocyanate group, and isothiocyanate group; R 4 represents a reactive silyl group represented by the formula: R 1 R 2 R 3 Si, a monovalent hydrocarbon group, or hydrogen atom; R 5 , R 6 , R 7 , and R 8 are a monovalent hydrocarbon group or hydrogen atom.

  以下是具有反应性硅基团的2,2'-联吡啶衍生物的一般式（1）： 其中，R1和R2代表从单价碳氢基团、有机氧基团、酰氧基团、羟基、卤素原子、氢原子、巯基、氨基、氰基、氰酸基团、异氰酸基团、硫氰酸基团和异硫氰酸基团中选择的取代基；R3代表单价的脂肪烯烃基团、有机氧基团、烷氧基团、酰氧基团、羟基、卤素原子、氢原子、巯基、氨基、氰基、氰酸基团、异氰酸基团、硫氰酸基团和异硫氰酸基团；R4代表代表公式R1R2R3Si的反应性硅基团、单价碳氢基团或氢原子；R5、R6、R7和R8是单价碳氢基团或氢原子。
• Luminescence switch-on assay of interferon-gamma using a G-quadruplex-selective iridium(<scp>iii</scp>) complex
  作者：Sheng Lin、Bingyong He、Chao Yang、Chung-Hang Leung、Jean-Louis Mergny、Dik-Lung Ma

  DOI：10.1039/c5cc06655g

  日期：——

  A novel luminescent G-quadruplex-selective iridium(iii) complex was employed in a G-quadruplex-based detection assay for IFN-γ.

  一种新型的发光G四链体选择性铱（iii）配合物被应用于基于G四链体的IFN-γ检测方法。