4-(tert-butyldimethylsilyloxy) butyl vinyl ether | 197230-93-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4-(tert-butyldimethylsilyloxy) butyl vinyl ether
• 英文别名: 4-(t-Butyldimethylsilyloxy)butyl vinyl ether；tert-butyl-(4-ethenoxybutoxy)-dimethylsilane
• CAS: 197230-93-6
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: YSRMIFMHJVOTBX-UHFFFAOYSA-N

物化性质

• 沸点：
  250.3±23.0 °C(Predicted)
• 密度：
  0.852±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(tert-butyldimethylsilyloxy) butyl vinyl ether 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 四丁基氟化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 25.0~170.0 ℃ 、6.67 Pa 条件下， 反应 6.5h， 生成 2-methyl-2-phenyl-1,3-dioxepane
  参考文献：
  名称：

  Direct Synthesis of Cyclic Ketals of Acetophenones by Palladium-Catalyzed Arylation of Hydroxyalkyl Vinyl Ethers

  摘要：

  Reaction of 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, or di(ethylene glycol) vinyl ether with aryl triflates, aryl bromides, or iodobenzene in presence of a catalytical amount of palladium acetate and the bidentate ligand DPPP provides a direct entry to cyclic ketals of acetophenones. It is postulated that the reaction proceeds via an initial alpha-arylation of the vinyl ethers to give labile aryl vinyl ether intermediates, which undergo subsequent ketalization in presence of protons in the reaction media. The method merits attention due to the simplicity of the experimental procedure and the possibility of selective ketal formation in the presence of an additional carbonyl group.

  DOI：

  10.1021/jo971454q
• 作为产物：
  描述：

  4-羟丁基乙烯基醚 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到4-(tert-butyldimethylsilyloxy) butyl vinyl ether
  参考文献：
  名称：

  Direct Synthesis of Cyclic Ketals of Acetophenones by Palladium-Catalyzed Arylation of Hydroxyalkyl Vinyl Ethers

  摘要：

  Reaction of 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, or di(ethylene glycol) vinyl ether with aryl triflates, aryl bromides, or iodobenzene in presence of a catalytical amount of palladium acetate and the bidentate ligand DPPP provides a direct entry to cyclic ketals of acetophenones. It is postulated that the reaction proceeds via an initial alpha-arylation of the vinyl ethers to give labile aryl vinyl ether intermediates, which undergo subsequent ketalization in presence of protons in the reaction media. The method merits attention due to the simplicity of the experimental procedure and the possibility of selective ketal formation in the presence of an additional carbonyl group.

  DOI：

  10.1021/jo971454q

文献信息

• An efficient synthesis of indane-derived bis(oxazoline) and its application to hetero Diels–Alder reactions on polymer support
  作者：Michio Kurosu、James R Porter、Michael A Foley

  DOI：10.1016/j.tetlet.2003.10.097

  日期：2004.1

  Indane-derived bis(oxazolines) were synthesized in two steps and 93% overall yield starting from commercially available substrates. This ligand is as effective as tert-butyl bis(oxazoline) in hetero Diels–Alder reaction both in solution and on polymer support.

  从市售底物开始，分两步合成了茚满衍生的双（恶唑啉），总产率为93％。该配体在溶液和聚合物载体上的杂Diels-Alder反应中与叔丁基双（恶唑啉）一样有效。
• 10.1021/acscatal.4c02211
  作者：Guan, Meihui、Yin, Ting、Wang, Yue、Miao, Huanran、Zhang, Ge、Zhang, Qian

  DOI：10.1021/acscatal.4c02211

  日期：——

  with alkynyl trifluoroborates is described, proceeding through a cobalt hydride-mediated radical-polar crossover metal hydrogen-atom-transfer process. This method affords structurally diverse alkynyl-containing compounds in high yields under mild conditions and features a wide substrate scope, good functional group tolerance, and suitability for late-stage functionalization of relatively complex natural

  描述了钴催化的烯烃与三氟硼酸炔基的加氢炔基化反应，通过氢化钴介导的自由基极性交叉金属氢原子转移过程进行。该方法在温和条件下以高产率提供结构多样的含炔基化合物，具有底物范围广、官能团耐受性良好、适合相对复杂的天然产物和生物活性分子的后期功能化的特点。将范围扩大到烯基三氟硼酸盐进一步增加了所开发方法的实用性。这种方法为烯烃与亲核炔基/烯基试剂的自由基参与的炔基化和烯基化反应开辟了一条替代途径。
• Direct Synthesis of Cyclic Ketals of Acetophenones by Palladium-Catalyzed Arylation of Hydroxyalkyl Vinyl Ethers
  作者：Mats Larhed、Anders Hallberg

  DOI：10.1021/jo971454q

  日期：1997.10.1

  Reaction of 2-hydroxyethyl vinyl ether, 4-hydroxybutyl vinyl ether, or di(ethylene glycol) vinyl ether with aryl triflates, aryl bromides, or iodobenzene in presence of a catalytical amount of palladium acetate and the bidentate ligand DPPP provides a direct entry to cyclic ketals of acetophenones. It is postulated that the reaction proceeds via an initial alpha-arylation of the vinyl ethers to give labile aryl vinyl ether intermediates, which undergo subsequent ketalization in presence of protons in the reaction media. The method merits attention due to the simplicity of the experimental procedure and the possibility of selective ketal formation in the presence of an additional carbonyl group.