1-(phenyl)non-2-en-7-yn-1-one

• 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-(phenyl)non-2-en-7-yn-1-one
• 英文别名: (E)-1-phenylnon-2-en-7-yn-1-one
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: LLIXOZATSIHPJF-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(phenyl)non-2-en-7-yn-1-one 在 bis(1,5-cyclooctadiene)nickel (0) 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以52%的产率得到(1RS,5SR)-2-methyl-3-(phenyl)bicyclo[3.3.0]oct-2-en-1-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：

  2-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 3.66h， 生成 1-(phenyl)non-2-en-7-yn-1-one
  参考文献：
  名称：

  Synthesis of High-Value 1,6-Enynes by Tandem Fragmentation/Olefination

  摘要：

  A tandem process provides high-value 1,6-enynes that are otherwise difficult to prepare. Two base-mediated reactions-fragmentation and olefination-are executed in a coordinated manner that is overall more efficient than either reaction on its own. The 1,6-enynes can be strategically employed in conjunction with carbocyclization to deliver important targets, as noted for reported syntheses of hirsutene and illudol.

  DOI：

  10.1021/ol401839e

文献信息

• Nickel-Catalyzed Cyclizations and Couplings with Vinylzirconium Reagents
  作者：Yike Ni、Kande K. D. Amarasinghe、John Montgomery

  DOI：10.1021/ol025812+

  日期：2002.5.1

  [reaction: see text] 1,3-Dienes were prepared by a variety of nickel-catalyzed couplings and cyclization processes. Intermolecular or partially intramolecular couplings of alkynes, vinylzirconium reagents, and either aldehydes or enones efficiently proceeded to generate a broad range of functionalized dienes.

  [反应：见正文] 1,3-二烯是通过各种镍催化的偶联和环化过程制备的。炔烃，乙烯基锆试剂以及醛或烯酮的分子间或部分分子内偶联有效地进行，以产生各种官能化的二烯。
• Palladium(0)-catalyzed cis-selective alkylative and arylative cyclization of alkynyl enones with organoboron reagents
  作者：Hirokazu Tsukamoto、Takamichi Suzuki、Tomomi Uchiyama、Yoshinori Kondo

  DOI：10.1016/j.tetlet.2008.04.111

  日期：2008.6

  A palladium(0)-tricyclohexylphosphine catalyzes cis-selective alkylative and arylative cyclization of alkyne-containing electron-deficient alkenes with organoboron reagents to provide five- or six-membered rings with exo tri- or tetra-substituted alkenes. The opposite stereoselectivity to that for the alkyne–aldehyde cyclization using the same reagents would result from palladacycle-forming oxidative

  钯（0）-三环己基膦与有机硼试剂一起催化含炔的缺电子的烯烃的顺式选择性烷基化和芳基化环化反应，以提供带有外三或四取代烯烃的五元或六元环。与使用相同试剂进行炔醛缩合反应的立体选择性相反，这是由于将Palladacycle形成了将底物氧化添加到Pd 0催化剂中，然后用硼试剂进行了重金属化，质子化和还原性消除作用而产生的。试剂的官能团相容性，可用性，稳定性和无毒性以及不需要添加剂的事实使该方法比Ni 0更实用-有机锌试剂催化环化反应。
• Chiral Cationic Cp^xRu(II) Complexes for Enantioselective Yne-Enone Cyclizations
  作者：David Kossler、Nicolai Cramer

  DOI：10.1021/jacs.5b08232

  日期：2015.10.7

  cyclopentadienyl (Cp) group is a ligand of great importance for many transition-metal complexes used in catalysis. Cationic CpRu(II) complexes with three free coordination sites are highly versatile catalysts for many atom-economic transformations. We report the synthesis of a family of Cp(x)Ru(II) complexes with chiral Cp ligands keeping the maximum number of available coordination sites. The cationic

  环戊二烯基 (Cp) 基团是许多用于催化的过渡金属配合物的重要配体。具有三个自由配位点的阳离子 CpRu(II) 配合物是用于许多原子经济转化的高度通用的催化剂。我们报告了具有手性 Cp 配体的 Cp(x)Ru(II) 复合物家族的合成，可保持最大数量的可用协调位点。阳离子成员是通过正式的异狄尔斯-阿尔德反应进行炔-烯酮环化的有效且选择性的催化剂。转化在 -20 °C 下进行 <1 小时，并提供高达 99:1 er 的吡喃。不饱和酯或 Weinreb-酰胺底物直接产生环烯醚萜骨架。
• Diverse Reactivity Manifolds of Alkynyl Enone- and Alkynyl Enal-Derived Nickelacycles:  Discovery of Nickel-Promoted [3+2] and [2+1] Cycloadditions
  作者：Sanjoy K. Chowdhury、Kande K. D. Amarasinghe、Mary Jane Heeg、John Montgomery

  DOI：10.1021/ja0012624

  日期：2000.7.1
• Cascade Cyclizations and Couplings Involving Nickel Enolates
  作者：Gireesh M. Mahandru、Andy R. L. Skauge、Sanjoy K. Chowdhury、Kande K. D. Amarasinghe、Mary Jane Heeg、John Montgomery

  DOI：10.1021/ja037423w

  日期：2003.11.1

  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.