2-((triisopropylsilyloxy)methyl)pent-4-en-1-ol | 1345697-98-4

• 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: 2-((triisopropylsilyloxy)methyl)pent-4-en-1-ol
• 英文别名: 2-[Tri(propan-2-yl)silyloxymethyl]pent-4-en-1-ol；2-[tri(propan-2-yl)silyloxymethyl]pent-4-en-1-ol
• CAS: 1345697-98-4
• 化学式: C₁₅H₃₂O₂Si
• 分子量: 272.503
• InChiKey: GLHRXYXQAZBIJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((triisopropylsilyloxy)methyl)pent-4-en-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 乙醚 为溶剂， 以42%的产率得到
  参考文献：
  名称：

  Intramolecular palladium-catalyzed alkene carboalkynylation

  摘要：

  Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbonyl compounds as nucleophiles and an alkynyl bromide as an electrophile, the reaction gives access to cyclopentanes in 44-93% yield and one example of cyclohexane in 31% yield with simultaneous formation of a SP3-SP C-C bond. The reaction therefore combines ring formation with the introduction of a versatile triple bond for further functionalization. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.030
• 作为产物：
  描述：

  烯丙基丙二酸二甲酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 mineral oil 为溶剂， 生成 2-((triisopropylsilyloxy)methyl)pent-4-en-1-ol
  参考文献：
  名称：

  Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines

  摘要：

  The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of acetylenes is further exploited to access key building blocks for the synthesis of bioactive natural products.

  DOI：

  10.1021/ol2029383

文献信息

• Pd(0)-Catalyzed Oxy- and Aminoalkynylation of Olefins for the Synthesis of Tetrahydrofurans and Pyrrolidines
  作者：Stefano Nicolai、Jérôme Waser

  DOI：10.1021/ol2029383

  日期：2011.12.2

  The first Pd(0)-catalyzed intramolecular oxy- and aminoalkynylation of nonactivated olefins is reported. The reaction gives access to important tetrahydrofuran and pyrrolidine heterocycles with high diastereoselectivity. The unique synthetic potential of acetylenes is further exploited to access key building blocks for the synthesis of bioactive natural products.
• Intramolecular palladium-catalyzed alkene carboalkynylation
  作者：Stefano Nicolai、Peter Swallow、Jerome Waser

  DOI：10.1016/j.tet.2015.06.030

  日期：2015.9

  Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbonyl compounds as nucleophiles and an alkynyl bromide as an electrophile, the reaction gives access to cyclopentanes in 44-93% yield and one example of cyclohexane in 31% yield with simultaneous formation of a SP3-SP C-C bond. The reaction therefore combines ring formation with the introduction of a versatile triple bond for further functionalization. (C) 2015 Elsevier Ltd. All rights reserved.