4-chloro-3'-methoxycarbonylbiphenyl

• 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: 4-chloro-3'-methoxycarbonylbiphenyl
• 英文别名: 4'-chloro-biphenyl-3-carboxylic acid methyl ester；4'-Chlor-biphenyl-3-carbonsaeure-methylester；Methyl 4'-chloro[1,1'-biphenyl]-3-carboxylate；methyl 3-(4-chlorophenyl)benzoate
• 化学式: C₁₄H₁₁ClO₂
• 分子量: 246.693
• InChiKey: HUGWWAOXLBJUCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-3'-methoxycarbonylbiphenyl 在 1,1'-双(二苯基膦)二茂铁 、 potassium fluoride 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium diacetate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 44.0h， 生成 Methyl 3-[4-[4-(3-chlorophenyl)phenyl]phenyl]benzoate
  参考文献：
  名称：

  A Repetitive One-Step Method for Oligoarene Synthesis Using Catalyst-Controlled Chemoselective Cross-Coupling

  摘要：

  A method far oligoarene synthesis involving chemoselective cross-coupling as the key reaction was developed. Boronic acids with a chloro or trifluoromethanesulfonyloxy group were used as the monomer precursors with either of two chemoselective catalytic systems: Pd with P(t-Bu)(3), and Pd with 1,1'-bis(diphenylphosphino)ferrocene (DPPF). This method enabled elongation by one benzene unit in every step and thus reduced the number of steps required for elongation of oligoarene chains with well-defined lengths and sequences of substituted benzene rings.

  DOI：

  10.1021/ol200676k
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 、 氯代苯基三乙氧基硅烷 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以85%的产率得到4-chloro-3'-methoxycarbonylbiphenyl
  参考文献：
  名称：

  Very efficient and broad-in-scope palladium-catalyzed Hiyama cross-coupling. The role of water and copper(i) salts

  摘要：

  在Cu（i）和适量水的存在下，实现了芳基卤化物和芳基（三烷氧基）硅烷之间产率非常高的Pd催化交叉偶联。

  DOI：

  10.1039/c5ra03732h

文献信息

• A atom-efficient cross-coupling reaction of aryl iodides with triarylbismuths catalyzed by immobilization of palladium(II)-Schiff base complex in MCM-41
  作者：Caifeng Xu、Lin Yin、Bin Huang、Haiyi Liu、Mingzhong Cai

  DOI：10.1016/j.tet.2016.01.052

  日期：2016.4

  The first phosphine-free heterogeneous atom-efficient cross-coupling of aryl iodides with triarylbismuths was achieved in NMP using K2CO3 as base at 110 °C in the presence of 2 mol % of an MCM-41-immobilized palladium(II)-Schiff base complex [MCM-41-N,N-Pd(OAc)2], yielding a variety of unsymmetrical biaryls in good to excellent yields. This new heterogeneous palladium catalyst exhibits high catalytic

  在NMP中，在2 mol％固定有MCM-41的钯（II）存在下，使用K 2 CO 3作为碱，在NMP中实现了芳基碘化物与三芳基铋的首次无膦异质原子效率交叉偶联。-席夫碱配合物[MCM-41-N，N-Pd（OAc）2 ]，可产生多种不对称的联芳基，收率高至优异。这种新型的非均相钯催化剂显示出高催化活性，可以通过简单过滤反应溶液进行回收，并循环使用至少10次，而活性没有降低。我们的系统不仅避免使用膦配体，而且解决了钯催化剂回收和再利用的基本问题。
• Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics
  作者：Tanmay Chatterjee、Da Seul Lee、Eun Jin Cho

  DOI：10.1021/acs.joc.7b00413

  日期：2017.4.21

  extended study of [4 + 2] benzannulation reactions of 2-(hetero)aryl-substituted anilines with alkynes by visible light photocatalysis. The method requires the use of tBuONO as a diazotizing agent and 0.3 mol % of fac-Ir(ppy)3 as a photocatalyst at room temperature. The reaction proceeded in a chemo- and regioselective manner with high functional group tolerance under mild conditions allowing the preparation

  本文中，我们报道了2-（杂）芳基取代的苯胺与炔烃的[4 + 2]苯并环反应通过可见光催化的扩展研究。该方法需要在室温下使用t BuONO作为重氮化剂，并使用0.3 mol％的fac -Ir（ppy）3作为光催化剂。反应在温和条件下以化学和区域选择性方式进行，具有较高的官能团耐受性，从而可以以中等至高收率制备各种多环（杂）芳族化合物，包括菲。该方法适用于9-苯基菲的克规模合成。
• Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-Pyrrolidinones-stereochemical and lower side-chain optimization
  作者：Todd R. Elworthy、Denis J. Kertesz、Woongki Kim、Michael G. Roepel、Lina Quattrocchio-Setti、David B. Smith、Jahari Laurant Tracy、Audrey Chow、Fujun Li、Emma R. Brill、Leang K. Lach、Daren McGee、Diana S. Yang、San-San Chiou

  DOI：10.1016/j.bmcl.2004.01.063

  日期：2004.4

  A series of 7-[(5R)-substituted 2-oxo-1-pyrrolidinyl]-heptanoic acids were prepared, their isomeric purity determined, and pharmacologically evaluated. Lactams with affinity for the EP4 receptor displayed agonist behavior. The lower side-chain of the lactam template could be substituted to afford ligands (e.g., 17, 24, 30, 31, and 33) of high potency and greater than 1000-fold affinity for EP4 versus the other EP prostanoid receptors. (C) 2004 Elsevier Ltd. All rights reserved.
• Very efficient and broad-in-scope palladium-catalyzed Hiyama cross-coupling. The role of water and copper(<scp>i</scp>) salts
  作者：Carla I. Traficante、Ernesto G. Mata、Carina M. L. Delpiccolo

  DOI：10.1039/c5ra03732h

  日期：——

  A very high-yielding Pd-catalyzed cross-coupling between aryl halides and aryl(trialkoxy)silanes is achieved in the presence of Cu(i) and a measured amount of water.

  在Cu（i）和适量水的存在下，实现了芳基卤化物和芳基（三烷氧基）硅烷之间产率非常高的Pd催化交叉偶联。
• A Repetitive One-Step Method for Oligoarene Synthesis Using Catalyst-Controlled Chemoselective Cross-Coupling
  作者：Kei Manabe、Mai Ohba、Yuji Matsushima

  DOI：10.1021/ol200676k

  日期：2011.5.6

  A method far oligoarene synthesis involving chemoselective cross-coupling as the key reaction was developed. Boronic acids with a chloro or trifluoromethanesulfonyloxy group were used as the monomer precursors with either of two chemoselective catalytic systems: Pd with P(t-Bu)(3), and Pd with 1,1'-bis(diphenylphosphino)ferrocene (DPPF). This method enabled elongation by one benzene unit in every step and thus reduced the number of steps required for elongation of oligoarene chains with well-defined lengths and sequences of substituted benzene rings.