(S)-8-(trimethylsilyl)oct-6-yn-3-ol | 1021489-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-8-(trimethylsilyl)oct-6-yn-3-ol
• 英文别名: (3S)-8-trimethylsilyloct-6-yn-3-ol
• CAS: 1021489-58-6
• 化学式: C₁₁H₂₂OSi
• 分子量: 198.381
• InChiKey: DESSUJXSQCYDBR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-8-(trimethylsilyl)oct-6-yn-3-ol 、 苯甲醛 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙醚 为溶剂， 以83%的产率得到(2R,6S)-6-ethyl-2-phenyl-3-vinylidenetetrahydro-2H-pyran
  参考文献：
  名称：

  Enantioselective route to 3-vinylidene tetrahydropyrans and 3-vinylidene oxepanes based on a silyl-Prins cyclization

  摘要：

  A general method has been developed for the asymmetric synthesis of 3-vinylidene tetrahydropyrans and 3-vinylidene oxepanes based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with propargylsilanes. The observed excellent diastereoselectivity and a high asymmetric induction offer a new synthetic method with a wide scope and generality. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.123
• 作为产物：
  描述：

  diethylzinc 、 6-(trimethylsilyl)-4-hexynal 在 titanium(IV) isopropylate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.0h， 以67%的产率得到(S)-8-(trimethylsilyl)oct-6-yn-3-ol
  参考文献：
  名称：

  Enantioselective route to 3-vinylidene tetrahydropyrans and 3-vinylidene oxepanes based on a silyl-Prins cyclization

  摘要：

  A general method has been developed for the asymmetric synthesis of 3-vinylidene tetrahydropyrans and 3-vinylidene oxepanes based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with propargylsilanes. The observed excellent diastereoselectivity and a high asymmetric induction offer a new synthetic method with a wide scope and generality. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.123

文献信息

• Enantioselective route to 3-vinylidene tetrahydropyrans and 3-vinylidene oxepanes based on a silyl-Prins cyclization
  作者：Bartłomiej Furman、Magdalena Dziedzic、Iwona Justyniak

  DOI：10.1016/j.tet.2008.01.123

  日期：2008.3

  A general method has been developed for the asymmetric synthesis of 3-vinylidene tetrahydropyrans and 3-vinylidene oxepanes based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with propargylsilanes. The observed excellent diastereoselectivity and a high asymmetric induction offer a new synthetic method with a wide scope and generality. (c) 2008 Elsevier Ltd. All rights reserved.