2-trimethylsilylethynyl-2-cyclopentenol | 152202-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-trimethylsilylethynyl-2-cyclopentenol
• 英文别名: 2-(2-Trimethylsilylethynyl)cyclopent-2-en-1-ol
• CAS: 152202-55-6
• 化学式: C₁₀H₁₆OSi
• 分子量: 180.322
• InChiKey: IQRTXMCOXBZWQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  249.7±40.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-trimethylsilylethynyl-2-cyclopentenol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 120.0h， 生成 (R)-2-<(trimethylsilyl)ethynyl>-2-cyclopenten-1-ol
  参考文献：
  名称：

  Enantiocomplementary preparation of optically pure 2-trimethylsilylethynyl-2-cyclopentenol by homochiralization of racemic precursors: a new route to the key intermediate of 1,25-dihydroxycholecalciferol and vincamine

  摘要：

  Treatment of racemic 2-trimethylsilylethynyl-2-cyclopentenol [(+/-)-1] with vinyl acetate in the presence of lipase PS in toluene yielded a 1:1 mixture of the unreacted (S)-alcohol [(S)-1] and the (R)-acetate [(R)-7] which without isolation afforded the chirally homogeneous (R)-alcohol [(R)-1] in 73% overall yield on reaction with acetic acid in the same reaction medium in the presence of diisopropyl azodicarboxylate and triphenylphosphine, followed by reductive deacylation of the resulting (R)-acetate [(R)-7]. On the other hand, hydrolysis of the racemic acetate [(+/-)-7], obtained from [(+/-)-1], in a phosphate buffer solution in the presence of lipase PS yielded a 1:1 mixture of the (R)-alcohol [(R)-1] and the unreacted (S)-acetate [(S)-7] which without separation, furnished the enantiomerically homogeneous (S)-alcohol [(S)-1] in 75% overall yield on treatment with acetic acid under the above Mitsunobu conditions, followed by reductive deacylation of the resulting (S)-acetate [(S)-7].

  DOI：

  10.1016/s0957-4166(00)80151-2
• 作为产物：
  描述：

  2-碘-2-环戊烯-1-酮 在 sodium tetrahydroborate 、 copper(l) iodide 、 四(三苯基膦)钯 、 cerium(III) chloride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-trimethylsilylethynyl-2-cyclopentenol
  参考文献：
  名称：

  Enantiocomplementary preparation of optically pure 2-trimethylsilylethynyl-2-cyclopentenol by homochiralization of racemic precursors: a new route to the key intermediate of 1,25-dihydroxycholecalciferol and vincamine

  摘要：

  Treatment of racemic 2-trimethylsilylethynyl-2-cyclopentenol [(+/-)-1] with vinyl acetate in the presence of lipase PS in toluene yielded a 1:1 mixture of the unreacted (S)-alcohol [(S)-1] and the (R)-acetate [(R)-7] which without isolation afforded the chirally homogeneous (R)-alcohol [(R)-1] in 73% overall yield on reaction with acetic acid in the same reaction medium in the presence of diisopropyl azodicarboxylate and triphenylphosphine, followed by reductive deacylation of the resulting (R)-acetate [(R)-7]. On the other hand, hydrolysis of the racemic acetate [(+/-)-7], obtained from [(+/-)-1], in a phosphate buffer solution in the presence of lipase PS yielded a 1:1 mixture of the (R)-alcohol [(R)-1] and the unreacted (S)-acetate [(S)-7] which without separation, furnished the enantiomerically homogeneous (S)-alcohol [(S)-1] in 75% overall yield on treatment with acetic acid under the above Mitsunobu conditions, followed by reductive deacylation of the resulting (S)-acetate [(S)-7].

  DOI：

  10.1016/s0957-4166(00)80151-2

文献信息

• A Dynamic Kinetic Resolution of Allyl Alcohols by the Combined Use of Lipases and [VO(OSiPh3)3]
  作者：Shuji Akai、Kouichi Tanimoto、Yukiko Kanao、Masahiro Egi、Tomoko Yamamoto、Yasuyuki Kita

  DOI：10.1002/anie.200503765

  日期：2006.4.10
• Enantiocomplementary preparation of optically pure 2-trimethylsilylethynyl-2-cyclopentenol by homochiralization of racemic precursors: a new route to the key intermediate of 1,25-dihydroxycholecalciferol and vincamine
  作者：Seiichi Takano、Mahito Suzuki、Kunio Ogasawara

  DOI：10.1016/s0957-4166(00)80151-2

  日期：1993.5

  Treatment of racemic 2-trimethylsilylethynyl-2-cyclopentenol [(+/-)-1] with vinyl acetate in the presence of lipase PS in toluene yielded a 1:1 mixture of the unreacted (S)-alcohol [(S)-1] and the (R)-acetate [(R)-7] which without isolation afforded the chirally homogeneous (R)-alcohol [(R)-1] in 73% overall yield on reaction with acetic acid in the same reaction medium in the presence of diisopropyl azodicarboxylate and triphenylphosphine, followed by reductive deacylation of the resulting (R)-acetate [(R)-7]. On the other hand, hydrolysis of the racemic acetate [(+/-)-7], obtained from [(+/-)-1], in a phosphate buffer solution in the presence of lipase PS yielded a 1:1 mixture of the (R)-alcohol [(R)-1] and the unreacted (S)-acetate [(S)-7] which without separation, furnished the enantiomerically homogeneous (S)-alcohol [(S)-1] in 75% overall yield on treatment with acetic acid under the above Mitsunobu conditions, followed by reductive deacylation of the resulting (S)-acetate [(S)-7].