2-(4-phenylbut-3-ynyl)cyclopentanone | 626249-35-2

• 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: 2-(4-phenylbut-3-ynyl)cyclopentanone
• 英文别名: 2-(4-phenylbut-3-ynyl)cyclopentan-1-one
• CAS: 626249-35-2
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: ZJGMCONYZZKJEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(4-phenylbut-3-ynyl)cyclopentanone 在 bis(1,5-cyclooctadiene)nickel (0) 、 四甲基乙二胺 、 sodium hydride 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 3-phenyl-1,2,4,5,5a,6,7,8-octahydrocyclopenta[c]pentalen-2-ol
  参考文献：
  名称：

  Cascade Cyclizations and Couplings Involving Nickel Enolates

  摘要：

  A new strategy for effecting cascade cyclization processes using nickel enolates has been developed. Nickel enolates may be cleanly generated by the oxidative cyclization of an enal and alkyne with Ni(0), and the resulting enolate may be functionalized by a variety of alkylation processes. Partially and fully intramolecular versions of the process allow the rapid synthesis of complex polycyclics from simple achiral, acyclic precursors.

  DOI：

  10.1021/ja037423w
• 作为产物：
  描述：

  1-(1-吡咯烷)环戊烯 、 (4-iodobut-1-yn-1-yl)benzene 以 甲苯 为溶剂， 反应 18.0h， 以45%的产率得到2-(4-phenylbut-3-ynyl)cyclopentanone
  参考文献：
  名称：

  Cascade Cyclizations and Couplings Involving Nickel Enolates

  摘要：

  A new strategy for effecting cascade cyclization processes using nickel enolates has been developed. Nickel enolates may be cleanly generated by the oxidative cyclization of an enal and alkyne with Ni(0), and the resulting enolate may be functionalized by a variety of alkylation processes. Partially and fully intramolecular versions of the process allow the rapid synthesis of complex polycyclics from simple achiral, acyclic precursors.

  DOI：

  10.1021/ja037423w

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.