2-[5-(tert-butyldimethylsilyloxy)pent-3-ynyl]cyclopentanone | 1234391-52-6

• 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: 2-[5-(tert-butyldimethylsilyloxy)pent-3-ynyl]cyclopentanone
• 英文别名: 2-[5-[Tert-butyl(dimethyl)silyl]oxypent-3-ynyl]cyclopentan-1-one
• CAS: 1234391-52-6
• 化学式: C₁₆H₂₈O₂Si
• 分子量: 280.483
• InChiKey: YOPDWGAHMAJXFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  三乙基硅烷 、 2-[5-(tert-butyldimethylsilyloxy)pent-3-ynyl]cyclopentanone 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以99%的产率得到(3aRS,6aSR,E)-1-(2-tert-buthyldimethylsiloxyethylidene)-6a-triethylsiloxyoctahydropentalene
  参考文献：
  名称：

  A Facile Construction of Bi- or Tricyclic Skeletons by Nickel-Catalyzed Stereoselective Cyclization of Alkynylcycloalkanone

  摘要：

  A nickel-catalyzed intramolecular cyclization of alkynylalkanone in the presence of Et(3)SiH using an NHC ligand produced various carbo- and heterocycles In a stereoselective manner. The reaction would proceed via formation of oxanickelacycle followed by sigma-bond metathesis with silane to give a bi- or tricyclic compound.

  DOI：

  10.1021/ol101329d
• 作为产物：
  描述：

  2-(5-Hydroxypent-3-ynyl)cyclopentan-1-one 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到2-[5-(tert-butyldimethylsilyloxy)pent-3-ynyl]cyclopentanone
  参考文献：
  名称：

  A Facile Construction of Bi- or Tricyclic Skeletons by Nickel-Catalyzed Stereoselective Cyclization of Alkynylcycloalkanone

  摘要：

  A nickel-catalyzed intramolecular cyclization of alkynylalkanone in the presence of Et(3)SiH using an NHC ligand produced various carbo- and heterocycles In a stereoselective manner. The reaction would proceed via formation of oxanickelacycle followed by sigma-bond metathesis with silane to give a bi- or tricyclic compound.

  DOI：

  10.1021/ol101329d

文献信息

• A Facile Construction of Bi- or Tricyclic Skeletons by Nickel-Catalyzed Stereoselective Cyclization of Alkynylcycloalkanone
  作者：Nozomi Saito、Yasuyuki Sugimura、Yoshihiro Sato

  DOI：10.1021/ol101329d

  日期：2010.8.6

  A nickel-catalyzed intramolecular cyclization of alkynylalkanone in the presence of Et(3)SiH using an NHC ligand produced various carbo- and heterocycles In a stereoselective manner. The reaction would proceed via formation of oxanickelacycle followed by sigma-bond metathesis with silane to give a bi- or tricyclic compound.