(E)-1-trimethylsilyl-4-octen-1-yn-3-one | 227750-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-trimethylsilyl-4-octen-1-yn-3-one
• 英文别名: 1-Trimethylsilyl-4-octen-1-yl-3-one；(E)-1-trimethylsilyloct-4-en-1-yn-3-one
• CAS: 227750-97-2
• 化学式: C₁₁H₁₈OSi
• 分子量: 194.349
• InChiKey: DLGHYEWTWHLABM-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-trimethylsilyl-4-octen-1-yn-3-one 在 dimethyl sulfide borane 、 (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo<1,2-c><1,3,2>oxazaborole-borane 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.92h， 生成 (S)-(+)-3-辛醇
  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
• 作为产物：
  描述：

  (E)-1-Trimethylsilanyl-oct-4-en-1-yn-3-ol 在 manganese(IV) oxide 作用下， 以 正己烷 为溶剂， 生成 (E)-1-trimethylsilyl-4-octen-1-yn-3-one
  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

• A Synthesis of Petrofuran Based on the Enantioselective Reduction of 1-Trimethylsilyl-4-alken-1-yn-3-ones
  作者：J. Garcia、M. López、J. Romeu

  DOI：10.1055/s-1999-6183

  日期：1999.4

  Highly enantioenriched 4-alken-1-yn-3-ol moiety (1), present in many bioactive acetylenic metabolites from sponges, has been efficiently obtained by reduction of the parent 1-trimethyl-silyl-4-alken-1-yn-3-one (2) with Alpine-Borane or with BH3 · SMe2 in the presence of chiral oxazaborolidines, followed by desilylation of the resulting alcohol. This strategy has been applied to the first stereoselective synthesis of petrofuran 3.

  高度对映体富集的 4-alken-1-yn-3-ol 部分 (1) 存在于海绵的许多生物活性炔属代谢物中，通过还原母体 1-三甲基-甲硅烷基-4-alken-1-yn- 可以有效获得在手性恶唑硼烷存在下，与 Alpine-Borane 或 BH3·SMe2 进行 3-一 (2) 反应，然后对所得醇进行脱甲硅烷基化。该策略已应用于石油呋喃3的首次立体选择性合成。