1-((triisopropylsilyl)ethynyl)cyclopropanol | 208652-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((triisopropylsilyl)ethynyl)cyclopropanol
• 英文别名: 1-[2-Tri(propan-2-yl)silylethynyl]cyclopropan-1-ol
• CAS: 208652-28-2
• 化学式: C₁₄H₂₆OSi
• 分子量: 238.445
• InChiKey: KMRNZSODMUWDDF-UHFFFAOYSA-N

物化性质

• 沸点：
  278.8±19.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  1-((triisopropylsilyl)ethynyl)cyclopropanol 在 indium(III) triflate 、 C₄₅H₃₆ClP₂Ru 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到(Z)-2-((triisopropylsilyl)methylene)cyclopropanone
  参考文献：
  名称：

  Stereoselective, Dual-Mode Ruthenium-Catalyzed Ring Expansion of Alkynylcyclopropanols

  摘要：

  A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or P-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.

  DOI：

  10.1021/ja807894t
• 作为产物：
  描述：

  三异丙基硅基乙炔 、 iodomagnesium salt of cyclopropanol hemiacetal 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以84%的产率得到1-((triisopropylsilyl)ethynyl)cyclopropanol
  参考文献：
  名称：

  Stereoselective, Dual-Mode Ruthenium-Catalyzed Ring Expansion of Alkynylcyclopropanols

  摘要：

  A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or P-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.

  DOI：

  10.1021/ja807894t

文献信息

• Rearrangement of 1-(1-Alkynyl)cyclopropanols to 2-Cyclopentenones via Their Hexacarbonyldicobalt Complexes. A New Use of Alkyne−Co₂(CO)₆ Complexes in Organic Synthesis
  作者：Nobuharu Iwasawa、Takeshi Matsuo、Mari Iwamoto、Taketo Ikeno

  DOI：10.1021/ja9734004

  日期：1998.4.1

  protective group of the substrates. This rearrangement was successfully applied to cyclopentenone annulation reactions onto cycloalkenes. An efficient synthesis of alkynyl-substituted bicyclo[n.1.0]alkanol derivatives from the corresponding cycloalkenes according to Danheiser's protocol was developed, and bicyclic cyclopentenones were obtained in moderate to good yield by applying to these the cobalt-mediated

  1-(1-炔基) 环丙醇向 2-环戊烯-1-酮的新重排是在其炔基部分与八羰基二钴 (Co2(CO8)) 络合后进行的。1-(1-炔基) 环丙醇在其炔烃末端具有广泛的取代基，以良好的产率重排为相应的 3-取代的 2-环戊烯-1-酮。In case of the reactions of 1-alkynylcyclopropanols with an alkyl substituent on the cyclopropane ring, either 4-substituted or 5-substituted 2-cyclopenten-1-ones could be selectively obtained by appropriate choice of stereochemistry and protective group of the substrates. 这种重排成功地应用于环戊烯酮环化成环烯烃的反应。根据