(S)-4-methyl-1-trimethylsilylhex-1-yn-3-one | 87569-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-methyl-1-trimethylsilylhex-1-yn-3-one
• 英文别名: (4S)-4-Methyl-1-(trimethylsilyl)hex-1-yn-3-one；(4S)-4-methyl-1-trimethylsilylhex-1-yn-3-one
• CAS: 87569-10-6
• 化学式: C₁₀H₁₈OSi
• 分子量: 182.338
• InChiKey: QKBZSGYDDBXVJV-VIFPVBQESA-N

物化性质

• 沸点：
  88 °C(Press: 20 Torr)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (S)-4-methyl-1-trimethylsilylhex-1-yn-3-one 在 potassium permanganate 、 lithium aluminium tetrahydride 作用下， 生成 S-(-)-2-甲基-1-丁醇
  参考文献：
  名称：

  Chiral acetylenes as synthetic intermediates. 4. Synthesis and chiroptical properties of optically active .alpha.,.beta.-acetylenic ketones

  摘要：

  DOI：

  10.1021/jo00173a021
• 作为产物：
  描述：

  (S)-(+)-2-甲基丁酸 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 51.5h， 生成 (S)-4-methyl-1-trimethylsilylhex-1-yn-3-one
  参考文献：
  名称：

  A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones

  摘要：

  The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00905-4

文献信息

• Stereoselective reduction of α′-branched α,β-ynones. Application to the synthesis of the Octalactin A ring
  作者：Jordi Bach、Jordi Garcia

  DOI：10.1016/s0040-4039(98)01420-8

  日期：1998.9

  A flexible, efficient route to chiral 3-hydroxy-4-methyl- and 3-hydroxy-4-methoxyalkanoic acids, with high control of the C(3) configuration, has been disclosed, which is based on the borane-mediated reduction of 1-trimethylsilyl-1-alkyn-3-ones (6) in the presence of oxazaborolidine 7 followed by hydroboration of the resulting propargylic alcohols 4 and 5. This strategy has been applied to the synthesis of the Octalactin A ring. (C) 1998 Elsevier Science Ltd. All rights reserved.
• GIACOMELLI, G.;ROSINI, C.;CAPORUSSO, A. M.;PALLA, F., J. ORG. CHEM., 1983, 48, N 25, 4887-4891
  作者：GIACOMELLI, G.、ROSINI, C.、CAPORUSSO, A. M.、PALLA, F.

  DOI：——

  日期：——
• FALORNI M.; LARDICCI L.; GIACOMELLI G., GAZZ. CHIM. ITAL., 117,(1987) N 1, 7-10
  作者：FALORNI M.、 LARDICCI L.、 GIACOMELLI G.

  DOI：——

  日期：——
• A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones
  作者：Carme Alemany、Jordi Bach、Jordi Garcia、Marta López、Ana B. Rodrı́guez

  DOI：10.1016/s0040-4020(00)00905-4

  日期：2000.11

  The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chiral acetylenes as synthetic intermediates. 4. Synthesis and chiroptical properties of optically active .alpha.,.beta.-acetylenic ketones
  作者：Giampaolo Giacomelli、Carlo Rosini、Anna Maria Caporusso、Fabio Palla

  DOI：10.1021/jo00173a021

  日期：1983.12