1-氟-4-(2-苯基乙基)苯 | 370-76-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-氟-4-(2-苯基乙基)苯
• 英文名称: 1-fluoro-4-phenethylbenzene
• 英文别名: Bibenzyl, 4-fluoro-；1-fluoro-4-(2-phenylethyl)benzene
• CAS: 370-76-3
• 化学式: C₁₄H₁₃F
• 分子量: 200.256
• InChiKey: LGAWAQNSZFCGMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  1-氟-4-(2-苯基乙基)苯 生成 1-phenyl-5-((thiophen-2-ylmethyl)thio)-1H-tetrazole
  参考文献：
  名称：

  YAMASHITA, A.;TOY, A.;SCAHILL, T. A., J. ORG. CHEM., 54,(1989) N5, C. 3625-3634

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氟-4-苯基乙炔-苯 在 乙醇 、 镍 作用下， 生成 1-氟-4-(2-苯基乙基)苯
  参考文献：
  名称：

  一些氟取代的甲苯

  摘要：

  p-Trifluoromethyltolane 和 p-fluorotolane 是通过氨基钠或钾在液氨中对对位取代的 1,1-二苯基-2-溴乙烯的作用合成的。几何异构体...

  DOI：

  10.1139/v55-199

文献信息

• “Bulky-Yet-Flexible” α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air
  作者：Xu-Wen Yang、Dong-Hui Li、A-Xiang Song、Feng-Shou Liu

  DOI：10.1021/acs.joc.0c01509

  日期：2020.9.18

  regioselective and efficient reductive Heck reaction, a series of moisture- and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the“bulky-yet-flexible”palladium complexes allowed highly anti-Markovnikov-selective

  为了进行高度区域选择性和高效的还原性Heck反应，合理设计，易于合成和充分表征了一系列湿气和空气稳定的α-二亚胺钯预催化剂。研究了钯配合物的结构与催化性能之间的关系。揭示了“大而尚柔的”钯配合物在好氧条件下可以使烯烃与（杂）芳基溴化物高度抗马尔科夫尼科夫选择性加氢芳基化。本方案的进一步合成应用可以提供对功能和生物活性分子的快速直接访问。
• Flash vacuum pyrolysis over magnesium. Part 1. Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides
  作者：R. Alan Aitken、Philip K. G. Hodgson、John J. Morrison、Adebayo O. Oyewale

  DOI：10.1039/b108663d

  日期：2002.1.23

  Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E,E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

  在玻璃棉上覆盖一层新升华的镁,进行闪式真空热解,能有效促使苄基卤化物耦合生成相应的联苄。当有邻位卤素取代基存在时,进一步脱卤生成部分二氢蒽和蒽。卤甲基萘和二苯基甲烷也能高效耦合,而三苯基氯甲烷则生成4,4′-双(二苯甲基)联苯。用α,α′-二卤代邻二甲苯可以获得较高产率的苯并环丁烯,而异构的α,α′-二卤代对二甲苯,通过形成的对二甲苯的聚合,可以得到一系列高热稳定性的聚合物。其他卤代烃苯大体上会脱卤化氢,某些情况下能产生环化反应。同样可以观察到,苯基卤代烷烃脱去羰基生成苯乙炔以及其他产物。简单的烷基卤化物则高效地脱去HCl或HBr生成烯烃。脂肪族二卤化物也会发生这一反应生成二烯,但不发生环化反应生成环烷烃,或在某些情况下发生氢原子转移的脱卤反应生成烯烃。5-溴戊-1-烯的产物符合自由基途径的预期,但6-溴己-1-烯并不符合。2,2-二氯丙烷和1,1-二氯丙烷能脱去HCl,但1,1-二氯丁烷、戊烷和己烷则能部分水解,随后脱去HCl,生成E,E-, E,Z-和Z,Z-异构体二烷-1-烯基醚,并且得到了这些物质的13C NMR全归属数据。6-氯己-1-炔和7-氯庚-1-炔能发生环化反应生成亚甲基环烷烃和环炔烃。本文还考察了1,2-二溴环己烷和1,2-二氯环辛烷在上述条件下的行为。本文给出了众多种证据,表明这些反应过程不涉及气相自由基的形成,而是表面吸附的金属有机物种。
• Chemoselective Hydrogenation of Alkynes to (<i>Z</i>)<i>-</i>Alkenes Using an Air-Stable Base Metal Catalyst
  作者：Viktoriia Zubar、Jan Sklyaruk、Aleksandra Brzozowska、Magnus Rueping

  DOI：10.1021/acs.orglett.0c01783

  日期：2020.7.17

  A highly selective hydrogenation of alkynes using an air-stable and readily available manganese catalyst has been achieved. The reaction proceeds under mild reaction conditions and tolerates various functional groups, resulting in (Z)-alkenes and allylic alcohols in high yields. Mechanistic experiments suggest that the reaction proceeds via a bifunctional activation involving metal–ligand cooperativity

  已经实现了使用空气稳定且易于获得的锰催化剂对炔烃的高度选择性加氢。该反应在温和的反应条件下进行并能耐受各种官能团，从而以高收率得到（Z）-烯烃和烯丙基醇。力学实验表明，该反应通过涉及金属-配体协同作用的双功能活化来进行。
• Substituent effects on the benzylic bond dissociation enthalpy in benzyl bromides (C–Br) and tert-butylbenzenes (C–CH3): a gas phase thermolysis and liquid phase photoacoustic study
  作者：Lucas J. J. Laarhoven、Jan G. P. Born、Isabel W. C. E. Arends、Peter Mulder

  DOI：10.1039/a702724i

  日期：——

  The bond dissociation enthalpies in a number of substituted benzyl bromides have been studied in the gas phase, using the toluene carrier technique, and in solution with photoacoustic calorimetry. Gas phase thermolysis with unsubstituted benzyl bromide gives an absolute C–Br bond dissociation enthalpy (Ed) at 298 K of 255 ± 4 kJ mol–1. Competition experiments in the gas phase reveal no substituent

  在气相中，使用甲苯载体技术，并在溶液中通过光声量热法研究了许多取代的苄基溴中的键解离焓。用未取代的苄基溴进行的气相热解在298 K下的绝对C-Br键离解焓（E d）为255±4 kJ mol –1。气相竞争实验表明，取代基对E d（C–Br）的值无影响。用取代的叔丁基苯进行气相热解对p -CN，p -OH和p -Bu t的C–CH 3键解离焓也没有影响取代基，在298 K时的E d（C–CH 3）值为299±2 kJ mol –1。在溶液中，与其他报道相反，光声实验对苄基溴的p -CN，p -Bu t和m -CF 3取代没有可检测的取代作用。通过光声量热法，发现所有研究的苄基溴的键解离焓为254±4 kJ mol –1。提供了对苄基键解离焓不存在取代基作用的原理。
• Palladium-Catalyzed Heck Coupling-Hydrogenation: Highly Efficient One-Pot Synthesis of Dibenzyls and Alkyl Phenyl Esters
  作者：M. Lakshmi Kantam、Rajashree Chakravarti、Venkat Reddy Chintareddy、B. Sreedhar、Suresh Bhargava

  DOI：10.1002/adsc.200800460

  日期：2008.11.3

  An efficient method for the synthesis of industrially important dibenzyls and alkyl phenyl esters via sequential Heck coupling and hydrogenation of the alkenyl double bond in one pot with a single recyclable catalyst under mild conditions has been realised. The catalyst was recovered by simple filteration and reused for several cycles with consistent activity.

  已经实现了一种有效的方法，该方法可通过顺序的Heck偶联和在一个罐中用一种可循环利用的催化剂在温和的条件下氢化烯基双键来进行工业上重要的二苄基和烷基苯基酯的合成。通过简单过滤回收催化剂，并以一致的活性重复使用数个循环。

表征谱图