1-isopropyl-2-(4'-methoxylphenylethynyl)benzene | 1172591-87-5

• 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: 1-isopropyl-2-(4'-methoxylphenylethynyl)benzene
• 英文别名: 1-isopropyl-2-((4-methoxyphenyl)ethynyl)benzene；1-Methoxy-4-[2-(2-propan-2-ylphenyl)ethynyl]benzene
• CAS: 1172591-87-5
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: IUWCTOWTADGUKY-UHFFFAOYSA-N

物化性质

• 熔点：
  141.4 °C
• 沸点：
  376.2±35.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-isopropyl-2-(4'-methoxylphenylethynyl)benzene 在 platinum(II) chloride 、 copper(I) bromide 作用下， 以 甲苯 为溶剂， 以72%的产率得到2-(4-methoxyphenyl)-1,1-dimethyl-1H-indene
  参考文献：
  名称：

  Yang, Shangdong; Li, Zigang; Jian, Xing, Angewandte Chemie - International Edition, 2009, vol. 48, p. 3999 - 4001

  摘要：

  DOI：
• 作为产物：
  描述：

  4-碘苯甲醚 、 2-碘异丙基苯 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 、 水 、 potassium hydroxide 作用下， 以 甲苯 、 甲醇 、 水 为溶剂， 反应 35.08h， 以81%的产率得到1-isopropyl-2-(4'-methoxylphenylethynyl)benzene
  参考文献：
  名称：

  One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes

  摘要：

  Unsymmetrical diarylalkynes are accessible by a one-pot procedure from two different aryl halides and (trimethylsilyl)acetylene. The three-component coupling is initialized by a Pd/Cu-catalyzed Sonogashira coupling of an aryl halide with (trimethylsilyl)acetylene. After subsequent desilylation Ilk; formed aryl(trimethylsilyl)acetylene with aqueous potassium hydroxide, a second Sono-gashira coupling with an aryl iodide that does not require any additional Pd/Cu-catalyst gives access to an unsymmetrical diarylalkyne.

  DOI：

  10.1021/jo100460v
• 作为试剂：
  描述：

  1-isopropyl-2-(phenylethynyl)benzene-d1 在 1-isopropyl-2-(4'-methoxylphenylethynyl)benzene 、 platinum(II) chloride 、 copper(I) bromide 作用下， 以 氘代甲苯 为溶剂， 以81%的产率得到1,1-dimethyl-2-phenyl-1H-indene-d1
  参考文献：
  名称：

  Yang, Shangdong; Li, Zigang; Jian, Xing, Angewandte Chemie - International Edition, 2009, vol. 48, p. 3999 - 4001

  摘要：

  DOI：

文献信息

• Synthesis of Functionalized 1<i>H</i>-Indenes via Copper-Catalyzed Arylative Cyclization of Arylalkynes with Aromatic Sulfonyl Chlorides
  作者：Xiaoming Zeng、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ja209300c

  日期：2011.11.9

  with commercially available aromatic sulfonyl chlorides that function as an aryl group donor. The reaction tolerates a broad range of functional groups, including bromide and iodide, nitrile, ketone, and nitro groups. The reaction allowed the synthesis of polycyclic aromatic hydrocarbons, such as a bis(indene), indacene, and fused polyarene derivatives, some of them showing strong fluorescence in solution

  多种多取代的 1H-茚可以通过铜催化的简单芳炔与用作芳基供体的市售芳族磺酰氯的芳基化环化反应来制备。该反应耐受广泛的官能团，包括溴化物和碘化物、腈、酮和硝基。该反应允许合成多环芳烃，例如双（茚）、茚和稠合聚芳烃衍生物，其中一些在溶液和固态中显示出强烈的荧光。
• Reusable Visible Light Photoredox Catalysts; Catalyzed Benzylic C(sp3)–H Functionalization/Carbocyclization Reactions
  作者：Jin-Heng Li、Jia-Dong Xia、Guo-Bo Deng、Ming-Bo Zhou、Wei Liu、Peng Xie

  DOI：10.1055/s-0032-1317349

  日期：——

  The C(sp(3))-H functionalization/carbocyclization reaction through the oxidative quenching of visible light photoredox catalysts is established for constructing functionalized 1H-indenes. The process is general for a wide range of benzylic C(sp(3))-H bonds and is highly compatible with common functional groups. Importantly, the visible light photoredox catalysts can be recovered and reused at least three times without loss of catalytic activity.
• Mechanisms of the PtCl₂-Catalyzed Intramolecular Cyclization of <i>o</i>-Isopropyl-Substituted Aryl Alkynes for the Synthesis of Indenes and Comparison of Three sp³ C–H Bond Activation Modes
  作者：Yi Wang、Wei Liao、Genping Huang、Yuanzhi Xia、Zhi-Xiang Yu

  DOI：10.1021/jo500839c

  日期：2014.6.20

  Chatani and He respectively reported an efficient way to synthesize indenes through PtCl2 catalyzed sp(3) C-H bond activation. Interestingly, the R group (R = H or Br) in the alkyne moiety of the substrates in Chatani's experiments migrates to the C3 position in indenes, whereas the R group (R = Ar) stays in the original C2 position of final indenes in He's experiments. DFT calculations indicated that there are two competing pathways a and c for the cyclization reaction. Pathway a involves [1,2]-R migration, [1,5]-H shift, and 4π-electrocyclization, giving the indenes with the R group at the C3 position. Pathway c takes place through irreversible [1,5]-H shift/cyclization and [1,2]-H shift, generating indenes with the R group at the C2 position. DFT calculations found that, when R = H or Br, pathway a is favored. When R = alkyl group, the [1,2]-R migration is difficult and pathway c is preferred. When R = Ar, DFT calculations predicted and experiments verified that both pathways a and c occur to give two indene products. Comparison of different models of sp(3) C-H activations has been presented to guide further understanding and prediction of new C-H bond activations.
• One-Pot Procedure for the Synthesis of Unsymmetrical Diarylalkynes
  作者：René Severin、Jessica Reimer、Sven Doye

  DOI：10.1021/jo100460v

  日期：2010.5.21

  Unsymmetrical diarylalkynes are accessible by a one-pot procedure from two different aryl halides and (trimethylsilyl)acetylene. The three-component coupling is initialized by a Pd/Cu-catalyzed Sonogashira coupling of an aryl halide with (trimethylsilyl)acetylene. After subsequent desilylation Ilk; formed aryl(trimethylsilyl)acetylene with aqueous potassium hydroxide, a second Sono-gashira coupling with an aryl iodide that does not require any additional Pd/Cu-catalyst gives access to an unsymmetrical diarylalkyne.
• Yang, Shangdong; Li, Zigang; Jian, Xing, Angewandte Chemie - International Edition, 2009, vol. 48, p. 3999 - 4001
  作者：Yang, Shangdong、Li, Zigang、Jian, Xing、He, Chuan

  DOI：——

  日期：——