2',5'-dimethoxy-[1,1'-biphenyl]-2-carbonitrile | 75860-41-2

• 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: 2',5'-dimethoxy-[1,1'-biphenyl]-2-carbonitrile
• 英文别名: 2',5'-dimethoxy-biphenyl-2-carbonitrile；2-cyano-2',5'-dimethoxybiphenyl；2-(2,5-Dimethoxyphenyl)benzonitrile
• CAS: 75860-41-2
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: OXBNMUIRLLFUHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  381.1±32.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2',5'-dimethoxy-[1,1'-biphenyl]-2-carbonitrile 在 双(乙腈)氯化钯(II) 、 水 、 silver trifluoroacetate 作用下， 以 N,N-二甲基乙酰胺 、 三氟乙酸 为溶剂， 反应 72.0h， 以74%的产率得到1,4-二甲氧基-9H-芴-9-酮
  参考文献：
  名称：

  Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

  摘要：

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

  DOI：

  10.1021/ol401063w
• 作为产物：
  描述：

  2-氰基苯硼酸 在 tripotassium phosphate "n" hydrate 、 Pd(PPh₃)₂Cl₂ 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 2',5'-dimethoxy-[1,1'-biphenyl]-2-carbonitrile
  参考文献：
  名称：

  Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

  摘要：

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

  DOI：

  10.1021/ol401063w

文献信息

• SRN1 C-arylation of phenols by azosulfides; A novel synthesis of dibenzo[b,d]pyran-6-ones
  作者：Giovanni Petrillo、Marino Novi、Carlo Dell'Erba、Cinzia Tavani

  DOI：10.1016/s0040-4020(01)96218-0

  日期：1991.11

  ortho-arylation of phenols by (2-cyanoaryl)azo t-butyl (or phenyl) sulfides in SRN1 conditions, followed by a silica-gel-catalysed lactonisation of the resulting 2-cyano-2′-hydroxybiphenyls, leads to dibenzo[b,d]pyran-6-ones.

  的邻位由（2-氰基芳）偶氮酚的-arylation吨丁基（或苯基）硫化物S中RN 1度的条件下，随后将得到的2-氰基-2'- hydroxybiphenyls的硅胶催化内酯化，导致二苯并[ b，d ]吡喃-6-。
• Investigations into the Suzuki–Miyaura coupling aiming at multikilogram synthesis of E2040 using (o-cyanophenyl)boronic esters
  作者：Yoshio Urawa、Hiroyuki Naka、Mamoru Miyazawa、Shigeru Souda、Katsuyuki Ogura

  DOI：10.1016/s0022-328x(02)01175-0

  日期：2002.7

  The Suzuki–Miyaura cross-coupling reaction between 1-3-bromo-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine ((R)-1b) and thermally unstable (o-cyanophenyl)boronic ester 6b in the presence of dichlorobis(triphenylphosphine)palladium and potassium phosphate hydrate in boiling toluene was found to afford 1-3-(2-cyanophenyl)-4-chloro-5-[1-(R)-fluoropropyl]}phenylpiperazine ((R)-5), an intermediate

  1- 3-溴-4-氯-5- [1-（R）-氟丙基]}苯基哌嗪（（R）-1b）与热不稳定的（邻氰基苯基）硼酸酯之间的Suzuki-Miyaura交叉偶联反应发现在沸腾的甲苯中在二氯双（三苯基膦）钯和磷酸钾水合物存在下，图6b得到1- 3-（2-氰基苯基）-4-氯-5- [1-（R）-氟丙基]}苯基哌嗪（ （R）-5），这是合成E2040的中间体，收率很高。通过实验设计（DOE）方法优化了交叉偶联的反应条件，发现该方法适用于富电子和/或空间位阻的芳基溴化物。还描述了用于生产（R）-5的安全性评估。
• Biaryl formation in the photochemical reaction of halogenated aromatic nitriles with methoxybenzenes
  作者：Khalid A. K. Al-Fakhri、Alec C. Mowatt、Albert C. Pratt

  DOI：10.1039/c39800000566

  日期：——

  Irradiation of tetrachloro- and tetrafluoro-phthalonitriles in the presence of anisole, 1,3-dimethoxy-benzene, or 1,4-dimethoxybenzene, led to formation of biaryls; a similar process occurred with mixtures of 1,4-dimethoxybenzene and 2- or 4-chlorobenzonitrile, but not 3-chlorobenzonitrile.

  在苯甲醚，1，3-二甲氧基苯或1，4-二甲氧基苯的存在下辐照四氯和四氟邻苯二甲腈导致形成联芳基。1,4-二甲氧基苯和2-或4-氯苄腈的混合物发生了类似的过程，但没有3-氯苄腈的混合物发生。
• AL-FAKHRI K. A. K.; MOWATT A. C.; PRATT A. C., J. CHEM. SOC. CHEM. COMMUN., 1980, NO 12, 566-568
  作者：AL-FAKHRI K. A. K.、 MOWATT A. C.、 PRATT A. C.

  DOI：——

  日期：——
• Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation
  作者：Jung-Chih Wan、Jun-Min Huang、Yu-Huei Jhan、Jen-Chieh Hsieh

  DOI：10.1021/ol401063w

  日期：2013.6.7

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.