4-methyl-3-(triethylsilyloxy)pentanal | 147753-24-0

• 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: 4-methyl-3-(triethylsilyloxy)pentanal
• 英文别名: 4-Methyl-3-(triethylsiloxy)pentanal；4-Methyl-3-triethylsilyloxypentanal
• CAS: 147753-24-0
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: BOVXZBFTKHXFJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-3-(triethylsilyloxy)pentanal 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (E)-N-Methoxy-N-methyl-5-hydroxy-6-methyl-2-heptenamide
  参考文献：
  名称：

  Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal-derived alkoxide nucleophiles

  摘要：

  Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.

  DOI：

  10.1021/jo00061a018
• 作为产物：
  描述：

  2-甲基-5-己烯-3-醇 在 吡啶 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-methyl-3-(triethylsilyloxy)pentanal
  参考文献：
  名称：

  A Strategy for Exploiting the Pseudosymmetry of the C1−C13 Stretch of Discodermolide

  摘要：

  The pseudo-C-2 symmetry of the C1 to C13 stretch of the discodermolide structure offers a potential strategic advantage for synthetic design Two approaches based on this recognition were devised, and one was shown to be effective in a model series.

  DOI：

  10.1021/ol049735p

文献信息

• Chelation-controlled stannylacetylene additions to β-alkoxy aldehydes promoted by alkylaluminum halide Lewis acids
  作者：David A. Evans、David P. Halstead、Brett D. Allison

  DOI：10.1016/s0040-4039(99)00740-6

  日期：1999.6

  Lewis acid-mediated additions of stannylacetylenes to β-alkoxy aldehydes are reported. High levels of chelation control are observed with dimethylaluminum chloride (Me2AlCl) and methylaluminum dichloride (MeAlCl2).

  报道了路易斯酸介导的苯乙烯基乙炔向β-烷氧基醛的加成。用二甲基氯化铝（Me 2 AlCl）和二氯化甲基铝（MeAlCl 2）观察到高水平的螯合控制。
• Evans David A., Gauchet-Prunet Joelle A., J. Org. Chem., 58 (1993) N 9, S 2446-2453
  作者：Evans David A., Gauchet-Prunet Joelle A.

  DOI：——

  日期：——
• Diastereoselective synthesis of protected syn 1,3-diols by base-catalyzed intramolecular conjugate addition of hemiacetal-derived alkoxide nucleophiles
  作者：David A. Evans、Joelle A. Gauchet-Prunet

  DOI：10.1021/jo00061a018

  日期：1993.4

  Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R2 = H, Me) and amides (X = N(Me)OMe, R2 = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported. The resulting benzylidene acetals are obtained in good yields (71-84%) and with high selectivity (>90: 10). In addition to an exploration of the scope of the reaction, a mechanistic study, involving the use of deuterated benzaldehyde to ascertain the rate-determining step of the process, is described.
• A Strategy for Exploiting the Pseudosymmetry of the C1−C13 Stretch of Discodermolide
  作者：Kathlyn A. Parker、Ioannis A. Katsoulis

  DOI：10.1021/ol049735p

  日期：2004.4.1

  The pseudo-C-2 symmetry of the C1 to C13 stretch of the discodermolide structure offers a potential strategic advantage for synthetic design Two approaches based on this recognition were devised, and one was shown to be effective in a model series.