3,5-bis(3-methoxyphenyl)pyridine | 15366-86-6

• 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
• 英文名称: 3,5-bis(3-methoxyphenyl)pyridine
• CAS: 15366-86-6
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: VZHNFFDDYMVTQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis(3-methoxyphenyl)pyridine 在 三溴化硼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-[3-[5-[3-[3-(dimethylamino)propoxy]phenyl]pyridin-3-yl]phenoxy]-N,N-dimethylpropan-1-amine
  参考文献：
  名称：

  Synthesis of 2,5- and 3,5-diphenylpyridine derivatives for DNA recognition and cytotoxicity

  摘要：

  A series of 2,5- and 3,5-diphenylpyridine derivatives was synthetised in high yields. A versatile chemical strategy allows the design of diphenylpyridines differently substituted with cationic or neutral side chains. The interaction of the molecules with DNA was investigated by biophysical and biochemical methods and an AT-binder (20) was characterised. A few cytotoxic molecules were identified but their antiproliferative activity does not correlate with DNA binding. Two compounds 18 and 22 showed significant antiproliferative activity and provide a novel route to potential anticancer agents. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.011
• 作为产物：
  描述：

  3,5-二溴吡啶 在 potassium phosphate 、 copper(l) iodide 、 N,N-二乙基乙二胺 、 sodium iodide 、 copper dichloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 3,5-bis(3-methoxyphenyl)pyridine
  参考文献：
  名称：

  铜催化的见解：铃木-宫浦的芳基/吲哚基硼酸酯交叉偶联中原位形成的纳米Cu 2 O

  摘要：

  已经研究了无配体铜催化3,5-二碘吡啶与芳基和吲哚硼酸酯的Suzuki-Miyaura偶联，收率良好。原位生成的纳米铜的2从氯化亚铜ø 2在反应条件下已经发现首次。通过5-碘嘧啶，碘吡啶，碘苯和二碘苯的芳基化进一步证明了反应的一般性，并产生了良好至中等的收率。此外，双吲哚生物碱Scalaridine A已成功地以60％的总收率合成。

  DOI：

  10.1021/acs.orglett.7b01669

文献信息

• COMPOUND COMPRISING PHENYL PYRIDINE UNITS
  申请人：Ye Qing

  公开号：US20090289547A1

  公开（公告）日：2009-11-26

  Organic compounds of formula I may be used in optoelectronic devices wherein R 1 is, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical; R2 is, independently at each occurrence, a C 1 -C 20 aliphatic radical, a C 3 -C 20 aromatic radical, or a C 3 -C 20 cycloaliphatic radical; a is, independently at each occurrence, an integer ranging from 0-4; b is, independently at each occurrence, an integer ranging from 0-3; Ar 1 is a direct bond or heteroaryl, aryl, or alkyl or cycloalkyl; Ar 2 is heteroaryl, aryl, or alkyl or cycloalkyl; c is 0, 1 or 2; and n is an integer ranging from 2-4.

  化学式I的有机化合物可用于光电子器件，其中R1在每次出现时独立地是C1-C20脂肪基、C3-C20芳香基或C3-C20环脂肪基；R2在每次出现时独立地是C1-C20脂肪基、C3-C20芳香基或C3-C20环脂肪基；a在每次出现时独立地是0-4之间的整数；b在每次出现时独立地是0-3之间的整数；Ar1是直接键或杂环芳基、芳基、烷基或环烷基；Ar2是杂环芳基、芳基、烷基或环烷基；c为0、1或2；n是2-4之间的整数。
• Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies
  作者：Ta-Hsien Chuang、Yu-Chi Chen、Someshwar Pola

  DOI：10.1021/jo101394c

  日期：2010.10.1

  A series of disubstituted pyridine derivatives was synthesized from the corresponding acryloyl azides by acetic acid-promoted cycloaddition. This represents a novel and convenient synthetic approach to the symmetric 3,5-disubstituted pyridines. The nature of the substituent on the double bond and the utilized solvent were found to be crucial to the yield of pyridines. The reactivity of the acid-promoted

  通过乙酸促进的环加成反应，由相应的丙烯酰基叠氮化物合成了一系列双取代的吡啶衍生物。这代表了对称的3，5-二取代吡啶的新颖且方便的合成方法。发现双键上取代基的性质和所用溶剂对吡啶的产率至关重要。酸促进的环加成反应的反应性随芳基（例如苯基和吡啶基）的存在而增加。我们还通过13 C标记的肉桂酰叠氮化物的酸促进的环加成反应探索了全面的机理。由丙烯酰基叠氮化物通过乙酸促进的三分子缩合合成对称的3，5-二取代的吡啶。
• Triarylbismuthanes as Threefold Aryl-Transfer Reagents in Regioselective Cross-Coupling Reactions with Bromopyridines and Quinolines
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1002/ejoc.201402455

  日期：2014.8

  Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot

  公开了在 Pd 催化条件下使用溴吡啶和溴喹啉与三芳基铋作为亚化学计量量的三重偶联试剂的交叉偶联研究。与单-和二溴吡啶基底物的反应性很高，并且单-和双-偶联是区域选择性地进行的。以高产率形成了单芳基和二芳基吡啶库。一锅法提供了对称和不对称二芳基吡啶的简单直接合成。使用三芳基铋试剂实现了 2-溴和 3-溴喹啉的芳基化。该研究表明，三芳基铋可用作三重芳基化试剂，用于在 Pd 催化条件下通过与溴吡啶和溴喹啉偶联合成芳基吡啶和喹啉。
• Cu-Catalyzed Concise Synthesis of Pyridines and 2-(1<i>H</i>)-Pyridones from Acetaldehydes and Simple Nitrogen Donors
  作者：Ziyuan Li、Xiaoqiang Huang、Feng Chen、Chun Zhang、Xiaoyang Wang、Ning Jiao

  DOI：10.1021/ol5035996

  日期：2015.2.6

  A highly selective copper-catalyzed concise synthesis of 3,5-diarylpyridine and 2-(1H)-pyridone has been achieved through cascade Chichibabin-type cyclization, C(sp3)–C(sp3) cleavage, and aerobic oxidation. Azide, ceric ammonium nitrate (CAN), and 2-aminopyridine are disclosed as efficient nitrogen donors in this Cu-catalysis using O2 as the oxidant. Water and molecular oxygen were employed as the

  通过级联的Chichibabin型环化，C（sp 3）–C（sp 3）裂解和需氧氧化，已实现了高选择性铜催化的3,5-二芳基吡啶和2-（1 H）-吡啶酮的简明合成。在使用O 2作为氧化剂的Cu催化中，叠氮化物，硝酸铈铵（CAN）和2-氨基吡啶被公开为有效的氮供体。在氧合作用的情况下，水和分子氧被用作氧源。
• Metal-free synthesis of substituted pyridines from aldehydes and NH₄OAc under air
  作者：Rulong Yan、Xiaoqiang Zhou、Ming Li、Xiaoni Li、Xing Kang、Xingxing Liu、Xing Huo、Guosheng Huang

  DOI：10.1039/c4ra10880a

  日期：——

  method for the synthesis of substituted pyridines with aldehydes and NH4OAc under mild conditions using air as the oxidant was developed. This oxidative cyclization process involves direct C–H bond functionalization, C–C/C–N bond formation and C–C bond cleavage.

  开发了一种无金属的有效方法，该方法在温和条件下使用空气作为氧化剂合成醛和NH 4 OAc取代的吡啶。这种氧化环化过程涉及直接的C–H键功能化，C–C / C–N键形成和C–C键裂解。