1-乙炔基-4-(4-硝基苯基)苯 | 180056-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-乙炔基-4-(4-硝基苯基)苯
• 英文名称: 4-ethynyl-4′-nitro-1,1′-biphenyl
• 英文别名: 4-Ethynyl-4'-nitro-1,1'-biphenyl；1-ethynyl-4-(4-nitrophenyl)benzene
• CAS: 180056-60-4
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: MWABQZBKHRECMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙炔基-4-(4-硝基苯基)苯 在 potassium tert-butylate 、 氢气 作用下， 以 异丙醇 为溶剂， 130.0 ℃ 、1.5 MPa 条件下， 反应 2.0h， 以73.1 mg的产率得到4-(4-ethynylphenyl)aniline
  参考文献：
  名称：

  碳催化剂的选择性加氢：自由基的作用。

  摘要：

  在存在其他可还原的官能团（例如烯烃或炔烃）的情况下，硝基部分的选择性氢化是一项艰巨的任务。我们表明，碳基（无金属）催化剂可用于使用H2作为还原剂选择性还原取代的硝基基团，为取代贵金属催化剂提供了巨大的潜力，并为有机合成的简单和绿色策略做出了贡献。

  DOI：

  10.1021/acs.orglett.9b02432
• 作为产物：
  描述：

  4-溴-4'-硝基联苯 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 1-乙炔基-4-(4-硝基苯基)苯
  参考文献：
  名称：

  非线性光学的有机金属配合物。X.分子系统改变（环戊二烯基）的平方和立方超极化率双（膦）钌σ-芳基炔阴离子：钌的X射线晶体结构（（Ë）-4,4'--CCC 6 ħ 4 CHC 6 H ^ 4 NO 2）（PPH 3）2（η-C 5 H ^ 5）

  摘要：

  配合物的Ru（4,4'-CCC 6 H ^ 4 Ç 6 ħ 4 NO 2）（PPH 3）2（η-C 5 H ^ 5）和Ru（4,4'-CCC 6 H ^ 4 Ç CC 6 H ^ 4 NO 2（PPH）3）2（η-C 5 H ^ 5）已经准备好，后者的结构特点；它们属于一系列有机金属供体-桥-受体化合物，其中含有（环戊二烯基）双（膦）钌（II）中心作为供体，共轭芳基乙炔桥和硝基受体基团。为系列复合物的Ru（CCR）（PR'电化学数据3）2（η-C 5 H ^ 5）（RPH，4-C 6 H ^ 4 NO 2，R'博士中，Me; R = 4,4'-C 6 H 4 C 6 H 4 NO 2，（E）-4,4'-C 6 H 4 CHCHC 6 H4 NO 2，4,4'--C 6 H ^ 4 ÇCC 6 H ^ 4 NO 2，4,4'--C 6 H ^ 4 ÑCHC 6 H ^ 4 NO

  DOI：

  10.1016/s0022-328x(97)00411-7

文献信息

• Synthesis and Nonlinear Optical Properties of η⁵-Monocyclopentadienyliron(II) Acetylide Derivatives. X-ray Crystal Structures of [Fe(η⁵-C₅H₅)(DPPE)(<i>p</i>-C⋮CC₆H₄NO₂)] and [Fe(η⁵-C₅H₅)(DPPE)((<i>E</i>)-<i>p</i>-C⋮CC₆H₄C(H)C(H)C₆H₄NO₂)]
  作者：M. Helena Garcia、M. Paula Robalo、Alberto R. Dias、M. Teresa Duarte、Wim Wenseleers、G. Aerts、Etienne Goovaerts、Marie P. Cifuentes、Steph Hurst、Mark G. Humphrey、Marek Samoc、Barry Luther-Davies

  DOI：10.1021/om0104619

  日期：2002.5.1

  increase in γ upon replacing Ru by the more easily oxidizable Fe and upon chain-lengthening the delocalizable π-bridging unit (proceeding from 4-C6H4 to (E)-4,4‘-C6H4CHCHC6H4). X-ray crystallographic structures of complexes [Fe(η5-C5H5)(DPPE)(p-C⋮CC6H4NO2)] and [Fe(η5-C5H5)(DPPE)((E)-p-C⋮CC6H4C(H)C(H)C6H4NO2)] were studied in order to investigate the existence of π-back-donation suggested by spectroscopic

  一系列所述类型的新的乙炔化物络合物的[Fe（η 5 -C 5 H ^ 5）（P⌒P）（p -C⋮CC 6 H ^ 4 R）]（P⌒P= DPPE（= 1,2-双（二苯基膦基）乙烷），（R）-PROPHOS（=（R）-（+）-1,2-双（二苯基膦基）丙烷），R = NO 2，C 6 H 4 NO 2，（Z）-C（ H）C（H）C 6 H 4 NO 2，（E）-C（H）C（H）C 6 H 4 NO 2）已经通过从所述前体卤化物抽象合成的[Fe（η 5 -C 5 H ^ 5）（P⌒P）（I）]和完全表征。络合物的二次超极化率（β）已通过1064 nm处的超瑞利散射测定。研究了从4-硝基苯基乙炔基到4-硝基联苯基乙炔基和4-硝基-（E）-苯乙烯基乙炔基对乙炔链长度的非线性响应的影响，揭示了有机金属分子材料中最高的首次超极化率的值。上非线性效率的比较绘制化合物的相关公知的家庭的[Ru（η 5 -C 5
• Organometallic Complexes for Nonlinear Optics. 11.¹ Molecular Quadratic and Cubic Hyperpolarizabilities of Systematically Varied (Cyclopentadienyl)(triphenylphosphine)nickel σ-Arylacetylides
  作者：Ian R. Whittall、Marie P. Cifuentes、Mark G. Humphrey、Barry Luther-Davies、Marek Samoc、Stephan Houbrechts、André Persoons、Graham A. Heath、Denes Bogsányi

  DOI：10.1021/om961066z

  日期：1997.6.1

  complexes Ni(C⋮CR)(PPh3)(η-C5H5) (R = 4-C6H4NO2 (3), 4,4‘-C6H4C6H4NO2 (4), (E)-4,4‘-C6H4CHCHC6H4NO2 (5), (Z)-4,4‘-C6H4CHCHC6H4NO2 (6), 4,4‘-C6H4C⋮CC6H4NO2 (7), 4,4‘-C6H4NCHC6H4NO2 (8)) have been prepared. Electrochemical data for the series of complexes NiCl(PPh3)(η-C5H5) (1), Ni(C⋮CPh)(PPh3)(η-C5H5) (2), and 3−8 have been determined. Introduction of nitro substituent (in progressing from 2 to 3) results

  配合物的Ni（C⋮CR）（PPH 3）（η-C 5 H ^ 5）（R = 4-C 6 H ^ 4 NO 2（3），4,4'--C 6 H ^ 4 Ç 6 ħ 4 NO 2（4），（ê）-4,4'--C 6 H ^ 4 CH CHC 6 H ^ 4 NO 2（5），（ž）-4,4'--C 6 H ^ 4 CH CHC 6 H ^ 4 NO 2（在图6）中，已经制备了4,4'-C 6 H 4 C⋮CC 6 H 4 NO 2（7），4,4'-C 6 H 4 N CHC 6 H 4 NO 2（8）。为系列复合物的电化学数据的NiCl（PPH 3）（η-C 5 H ^ 5）（1），镍（C⋮CPH）（PPH 3）（η-C 5 H ^ 5）（2），和3 - 8已经确定。硝基取代基的引入（在进展从2到3）导致在镍大幅增加II / III的氧化电位，所有这些都对从一环进展丢失（3），以两环（4 - 8）发色
• Organometallic complexes for non-linear optics XII syntheses and second-order susceptibilities of (neomenthyldiphenylphosphine) gold σ-arylacetylides: X-ray crystal structures of Au(C≡CPh) (nmdpp) and Au((E)-4,4′-C≡CC6H4CH=CHC6H4NO2)(nmdpp)
  作者：Ian R. Whittall、Mark G. Humphrey、Marek Samoc、Barry Luther-Davies、David C.R. Hockless

  DOI：10.1016/s0022-328x(97)00196-4

  日期：1997.10

  The series of complexes Au(C=CR)(nmdpp) (R = Ph (2), 4-C6H4NO2 (3), 4,4'-C6H4C6H4NO2 (4), (E)-4,4'-C6H4CH=CHC6H4NO2 (5), (Z)-4,4'-C6H4CH=CHC6H4NO2 (6), 4,4'-C6H4C=CC6H4NO2 (7), 4,4'-C6H4N=CHC6H4NO2 (8); nmdpp = (+)-neomenthyldiphenylphosphine) has been synthesized by reaction of AuCl(nmdpp) with the corresponding acetylene and methoxide in the presence of trace amounts of a phosphine oxide, and complexes 2 and 5 have been structurally characterized. Complexes 2-8 and analogous (triphenylphosphine)gold acetylides and precursor (phosphine)gold chlorides have been examined for their second-order bulk susceptibilities chi((2)) by the Kurtz powder technique, with the largest response (ca. 2 x urea) being that from 3. (C) 1997 Elsevier Science S.A.
• Organometallic Complexes for Nonlinear Optics. 8.¹ Syntheses and Molecular Quadratic Hyperpolarizabilities of Systematically Varied (Triphenylphosphine)gold σ-Arylacetylides:  X-ray Crystal Structures of Au(C⋮CR)(PPh₃) (R = 4-C₆H₄NO₂, 4,4‘-C₆H₄C₆H₄NO₂)
  作者：Ian R. Whittall、Mark G. Humphrey、Stephan Houbrechts、André Persoons、David C. R. Hockless

  DOI：10.1021/om960673j

  日期：1996.12.24

  The series of complexes Au(C=CR)(PPh(3)) (R=Ph (2), 4-C6H4NO2 (3), 4,4'-C6H4C6H4NO2 (4), (E)-4,4'-C6H4CH=CHC6H4O2 (5), (Z)-4,4'-C6H4CH=CHC6H4NO2 (6), 4,4'-C6H4C=CC6H4NO2 (7), 4,4'-C6H4N=CHC6H4NO2 (8)) have been synthesized by reaction of AuCl(PPh(3)) with the corresponding acetylene and methoxide, and complexes 3-8 have been structurally characterized. The molecular first hyperpolarizabilities for the complexes have been determined by hyper-Rayleigh scattering at 1064 nm. Introduction of the nitro substituent (in proceeding from 2 to 3) leads to a significant increase in nonlinearity. Experimental beta values increase as 3 < 4 < 6 approximate to 7 < 8 < 5 consistent with nonlinearity increasing with (i) chain lengthening, (ii) replacing biphenyl (4) or yne linkage (7) by ene linkage (5), (iii) replacing (Z)-ene stereochemistry (6) with (E)-ene stereochemistry (5), and (iv) ene linkage (5) being more efficient than imino linkage (8). The same trend is observed with two-level-corrected data. A linear correlation of both experimentally-determined and two-level-corrected nonlinearities of the acetylides with precursor acetylenes is observed.
• Syntheses, Structure, and Molecular Cubic Hyperpolarizabilities of Systematically Varied Ethynylgold(I) Complexes
  作者：José Vicente、María Teresa Chicote、María Dolores Abrisqueta、M. Carmen Ramírez de Arellano、Peter G. Jones、Mark G. Humphrey、Marie P. Cifuentes、Marek Samoc、Barry Luther-Davies

  DOI：10.1021/om000093t

  日期：2000.8.1

  The reactions of Q[Au(acac)(2)] (Q = N(PPh3)(2) (PPN; a), NPr4 (b); acac = acetylacetonato) with terminal alkynes of the type HC=CC6H4R-4 in a 1:2 molar ratio affords the complexes Q[Au(C=CC6H4R-4)(2)] (R = NO2 (1), C6H4NO2-4 (2), (E)-CH=CHC6H4NO2-4 (3)). The same alkynes react with [AuCl(CNBut)] in NEt3 to give the complexes [Au(C=CC6H4R-4)(CNBut)] (R = NO2 (4), C6H4NO2-4 (5), (E)-CH=CHC6H4NO2-4 (6)). When NHEt2 is used instead of NEt3, attack of the secondary amine at the isonitrile ligand takes place and alkynyl carbene complexes of the type [Au(C=CC6H4R-4)C(NHBut)(NEt2)}] (R = NO2 (7), C6H4NO2-4 (8), (E)-CH=CHC6H4NO2-4 (9)) are obtained. The crystal structures of 1a, 4, 7, and 9 have been determined. The cubic hyperpolarizabilities of 1a,b, 4-6, 8, 9, and the related complexes [Au(C=CC6H4R-4)(PPh3)] (R = H (10), NO2 (11), 4-C6H4NO2 (12), (E)-CH=CHC6H4NO2-4 (13), C=CC6H4NO2-4 (14), (Z)-CH=CHC6H4NO2-4 (15), (E)-N=CHC6H4NO2-4 (16)) have been determined by Z-scans at 800 nm. An increase in gamma(real) is observed on replacing the coligand (BuNC)-N-t by PPh3 (proceeding from 5 to 12 and from 6 to 13), introduction of the NO2 group (proceeding from 10 to 11), extending the arylalkynyl pi-bridge (proceeding from 11 to 12-15), and replacing (Z)-CH=CH by the (E)-CH=CH linking unit (proceeding from 15 to 13).