(E)-1-Trimethylsilanyl-oct-4-en-1-yn-3-ol | 188349-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-Trimethylsilanyl-oct-4-en-1-yn-3-ol
• 英文别名: (E)-1-trimethylsilyloct-4-en-1-yn-3-ol
• CAS: 188349-75-9
• 化学式: C₁₁H₂₀OSi
• 分子量: 196.365
• InChiKey: GNHQNSGTABMJCS-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (E)-1-Trimethylsilanyl-oct-4-en-1-yn-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (E)-4-octen-1-yn-3-ol
  参考文献：
  名称：

  活化的乙磺酰胺和叔乙磺酰胺的无金属合成。

  摘要：

  描述了活化的炔磺酰胺和烯磺酰胺的操作简单的合成。可以通过在室温下短时间内使磺酰胺类化合物与活化的溴炔烃和Triton B反应来获得丙磺酰胺。同样，末端炔烃与磺酰胺反应以提供烯磺酰胺。Z / E磺酰胺可以仅转化为E磺酰胺。

  DOI：

  10.1039/c9ob00947g
• 作为产物：
  描述：

  (4E)-4-己烯醛 、 三甲基乙炔基硅 在 正丁基锂 作用下， 生成 (E)-1-Trimethylsilanyl-oct-4-en-1-yn-3-ol
  参考文献：
  名称：

  Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

  摘要：

  The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00251-7

文献信息

• Lipase catalysed resolution of (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols: useful intermediates for the synthesis of optically active γ-lactones
  作者：Pietro Allevi、Pierangela Ciuffreda、Mario Anastasia

  DOI：10.1016/s0957-4166(96)00475-2

  日期：1997.1

  Various (R)- and (S)-1-trimethylsilyl-1-alkyn-3-ols, chiral building units useful for the synthesis of biologically active compounds, have been efficiently resolved by enantioselective acetylation mediated by immobilized lipase PS. The resolution is applied to the synthesis of (R)- and (S)-5-octyl-2-(5H)-furanones. (C) 1997, Elsevier Science Ltd. All rights reserved.
• Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides
  作者：Lucile Andna、Laurence Miesch

  DOI：10.1039/c9ob00947g

  日期：——

  An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.

  描述了活化的炔磺酰胺和烯磺酰胺的操作简单的合成。可以通过在室温下短时间内使磺酰胺类化合物与活化的溴炔烃和Triton B反应来获得丙磺酰胺。同样，末端炔烃与磺酰胺反应以提供烯磺酰胺。Z / E磺酰胺可以仅转化为E磺酰胺。
• Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum
  作者：Jordi Garcia、Marta López、Joan Romeu

  DOI：10.1016/s0957-4166(99)00251-7

  日期：1999.7

  The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol, an immunosuppressive and antitumoral metabolite isolated from the Caribbean sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediated reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-one in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science Ltd. All rights reserved.