1-Phenylethynyl-2-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-cyclopentanol | 209533-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Phenylethynyl-2-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-cyclopentanol
• CAS: 209533-06-2
• 化学式: C₁₉H₂₂OSi
• 分子量: 294.469
• InChiKey: YULMCPPNQHZZFK-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-Phenylethynyl-2-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-cyclopentanol 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 苯 为溶剂， 反应 5.0h， 以86%的产率得到(2R,3R)-4-Phenylethynyl-2-trimethylsilanylethynyl-1-oxa-spiro[2.4]heptan-4-ol
  参考文献：
  名称：

  Two distinct epoxide ring opening pathways in a monocyclic model system of the kedarcidin chromophore

  摘要：

  Two monocyclic model compounds 2 and 3 were synthesized from (Z)-ketoeneyne 5 for studying the epoxide ring opening pathways related to activation of the kedarcidin chromophore (1). The solvent-derived S(N)1 products 8a,b and 9a,b were formed from 2 and 3 in MeOH while the S(N)2 products 10a,b were produced from 2 and 3 with methyl thioglycolate in buffer (pH 7.0)-iPrOH; the latter reaction may provide a new scenario for bioreductive activation of the kedarcidin chromophore via an S(N)2 attack of thiol at the propargylic carbon atom. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(98)00664-9
• 作为产物：
  描述：

  (Z)-2-(trifluoromethanesulfonyloxymethylene)cyclopentanone 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.17h， 生成 1-Phenylethynyl-2-[3-trimethylsilanyl-prop-2-yn-(Z)-ylidene]-cyclopentanol
  参考文献：
  名称：

  Two distinct epoxide ring opening pathways in a monocyclic model system of the kedarcidin chromophore

  摘要：

  Two monocyclic model compounds 2 and 3 were synthesized from (Z)-ketoeneyne 5 for studying the epoxide ring opening pathways related to activation of the kedarcidin chromophore (1). The solvent-derived S(N)1 products 8a,b and 9a,b were formed from 2 and 3 in MeOH while the S(N)2 products 10a,b were produced from 2 and 3 with methyl thioglycolate in buffer (pH 7.0)-iPrOH; the latter reaction may provide a new scenario for bioreductive activation of the kedarcidin chromophore via an S(N)2 attack of thiol at the propargylic carbon atom. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(98)00664-9