(3-(3-methoxyphenyl)prop-1-en-1-yl)trimethylsilane | 1075184-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3-(3-methoxyphenyl)prop-1-en-1-yl)trimethylsilane
• 英文别名: ((E)-3-(3-methoxyphenyl)prop-1-enyl)trimethylsilane；((E)-3-(3-Methoxyphenyl)prop-1-enyl)trimethylsilane；[(E)-3-(3-methoxyphenyl)prop-1-enyl]-trimethylsilane
• CAS: 1075184-35-8
• 化学式: C₁₃H₂₀OSi
• 分子量: 220.387
• InChiKey: DNJDUTUPENCZOS-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (3-(3-methoxyphenyl)prop-1-en-1-yl)trimethylsilane 在 sodium dihydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(3-(3-methoxybenzyl)oxiran-2-yl)trimethylsilane
  参考文献：
  名称：

  Carbocupration−Functionalization of Arynes: Rapid Access to Variably Ortho-Substituted ((E)-3-Phenylprop-1-enyl)silanes

  摘要：

  A consecutive three-component coupling reaction involving a lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, variably substituted ortho-arynes, and a selection of common electrophiles is described. The method affords readily functionalized homobenzylic vinylsilanes with exceptional E-diastereoselectivity and allows for in situ incorporation of carbon- or heteroatom-based electrophiles into the arene.

  DOI：

  10.1021/ol8021885
• 作为产物：
  描述：

  2-iodo-3-methoxyphenyl triflate 、 烯丙基三甲基硅烷 在 仲丁基锂 、 copper(l) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到(3-(3-methoxyphenyl)prop-1-en-1-yl)trimethylsilane
  参考文献：
  名称：

  Carbocupration−Functionalization of Arynes: Rapid Access to Variably Ortho-Substituted ((E)-3-Phenylprop-1-enyl)silanes

  摘要：

  A consecutive three-component coupling reaction involving a lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, variably substituted ortho-arynes, and a selection of common electrophiles is described. The method affords readily functionalized homobenzylic vinylsilanes with exceptional E-diastereoselectivity and allows for in situ incorporation of carbon- or heteroatom-based electrophiles into the arene.

  DOI：

  10.1021/ol8021885

文献信息

• Iron-Catalyzed Cross-Coupling of Functionalized Benzylmanganese Halides with Alkenyl Iodides, Bromides, and Triflates
  作者：Alexandre Desaintjean、Sophia Belrhomari、Lidie Rousseau、Guillaume Lefèvre、Paul Knochel

  DOI：10.1021/acs.orglett.9b03292

  日期：2019.11.1

  substituted benzylic manganese chlorides were prepared by insertion of magnesium turnings in the presence of MnCl2·2LiCl in THF at −5 °C within 2 h. These benzylic manganese reagents underwent smooth cross-couplings with various functionalized alkenyl iodides, bromides, and triflates or iodoacrylates in the presence of 10 mol % FeCl2 at 25 °C for 1–12 h. Mechanistic studies showed that benzylic manganese

  在MnCl 2 ·2LiCl的存在下，在-5°C的THF中，在2小时内插入镁屑，制备了各种取代的苄基氯化锰。这些苄基锰试剂在25℃下在10 mol％FeCl 2存在下与各种官能化的烯基碘化物，溴化物和三氟甲酸酯或碘丙烯酸酯进行平滑的交叉偶联1–12小时。机理研究表明，在FeCl 2的存在下，苄基卤化锰产生了一种非常活泼的铁酸盐络合物。
• Carbocupration−Functionalization of Arynes: Rapid Access to Variably Ortho-Substituted ((<i>E</i>)-3-Phenylprop-1-enyl)silanes
  作者：Ashok Ganta、Timothy S. Snowden

  DOI：10.1021/ol8021885

  日期：2008.11.20

  A consecutive three-component coupling reaction involving a lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, variably substituted ortho-arynes, and a selection of common electrophiles is described. The method affords readily functionalized homobenzylic vinylsilanes with exceptional E-diastereoselectivity and allows for in situ incorporation of carbon- or heteroatom-based electrophiles into the arene.