1-(9'-anthracenyl)-2-triisopropylsilylethyne | 327187-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(9'-anthracenyl)-2-triisopropylsilylethyne
• 英文别名: 9-(triisopropylsilylethynyl)anthracene；Silane, (9-anthracenylethynyl)tris(1-methylethyl)-；2-anthracen-9-ylethynyl-tri(propan-2-yl)silane
• CAS: 327187-17-7
• 化学式: C₂₅H₃₀Si
• 分子量: 358.599
• InChiKey: JQSTZKABPAEGHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  460.6±18.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(9'-anthracenyl)-2-triisopropylsilylethyne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以59%的产率得到9-乙炔基蒽
  参考文献：
  名称：

  Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA

  摘要：

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.

  DOI：

  10.1021/acs.joc.5b01132
• 作为产物：
  描述：

  9-氯蒽 、 三异丙基硅基乙炔 在 双(乙腈)氯化钯(II) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以100%的产率得到1-(9'-anthracenyl)-2-triisopropylsilylethyne
  参考文献：
  名称：

  Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA

  摘要：

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.

  DOI：

  10.1021/acs.joc.5b01132

文献信息

• C(sp2)-C(sp) and C(sp)-C(sp) Coupling Reactions Catalyzed by Oxime-Derived Palladacycles
  作者：Diego A. Alonso、Carmen Nájera、Ma Carmen Pacheco

  DOI：10.1002/adsc.200303067

  日期：2003.9

  4′-dichlorobenzophenone, is an efficient pre-catalyst for the copper- and amine-free Sonogashira coupling between terminal acetylenes and aryl iodides and aryl and vinyl bromides achieving turnover numbers (TON) of up to 72000. Catalyst 8a has also been shown as a effective promoter for the sila-Sonogashira coupling between 1-(trimethylsilyl)alkynes and aryl iodides and bromides in the presence of CuI or

  衍生自4,4'-二氯二苯甲酮的肟衍生的氯桥式Palladacycle 8a是末端乙炔与芳基碘化物之间的无铜和无胺Sonogashira偶联的有效预催化剂，达到了营业额（TON ）最高可达72000。在CuI或Bu 4存在的情况下，催化剂8a还被证明是1-（三甲基甲硅烷基）炔烃与芳基碘化物和溴化物之间sila-Sonogashira偶联的有效促进剂。NBr作为助催化剂。这种配合物还能在室温下以TONs高达1000的效率有效地催化NMP中1-炔烃之间的均偶联反应（Glaser型偶联）。所有反应均可在空气中进行，并在极低的负载条件下使用试剂级化学物质，证明了肟衍生的palladacycles的多功能性和高活性。
• Palladium-Catalyzed Formation of Aceanthrylenes:  A Simple Method for Peri-Cyclopentenelation of Aromatic Compounds
  作者：Hung Dang、Miguel A. Garcia-Garibay

  DOI：10.1021/ja002329q

  日期：2001.1.1

  2(PPh3)2 (4.5 mol %), PPh3 (23 mol %), CuSO4/ Al2O3 (17 mol %), alkyne (400 mol %), Et3N (400 mol %), benzene (deoxygenated), refluxed 16 h. b Total isolated yield of 2 and 3 after chromatography. c Relative ratios determined by 1H NMR. d Sealed tube reactions were carried out at 110 °C with no copper.

  2(PPh3)2 (4.5 mol %)、PPh3 (23 mol %)、CuSO4/Al2O3 (17 mol %)、炔烃 (400 mol %)、Et3N (400 mol %)、苯（脱氧），回流 16 小时。b 层析后 2 和 3 的总分离产率。c 1H NMR 确定的相对比率。d 密封管反应在 110 °C 下进行，无铜。
• A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles
  作者：Diego A Alonso、Carmen Nájera、Ma̱ Carmen Pacheco

  DOI：10.1016/s0040-4039(02)02335-3

  日期：2002.12

  Oxime palladacycle derived from 4,4'-dichlorobenzophenone was found to promote the Sonogashira reaction of aryl iodides and aryl bromides with terminal acetylenes using I equivalent of tetrabutylammonium acetate in organic solvents generally in 1 h at 110degreesC and in high TONs (up to 72000). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA
  作者：Kan Takahashi、Shun Ito、Kosuke Nakamoto、Yasutomo Ito、Yoshihito Ueno

  DOI：10.1021/acs.joc.5b01132

  日期：2015.9.4

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.