2-(2-phenylacetyl)cyclopentanone | 62808-74-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-phenylacetyl)cyclopentanone
• 英文别名: 2-(2-phenylacetyl)cyclopentan-1-one；2-Phenylacetyl-cyclopentanon；2-Phenylacetylcyclopentanon
• CAS: 62808-74-6
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: NVFMGALWSAGMDB-UHFFFAOYSA-N

物化性质

• 沸点：
  340.2±30.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-phenylacetyl)cyclopentanone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 6-oxo-7-phenyl-heptanoic acid
  参考文献：
  名称：

  Untersuchungen �ber die Bildung von 2-Acylcyclopentanonen aus 1-(1-�thynyl)-cyclopentenen und Perameisens�ure

  摘要：

  DOI：

  10.1007/bf01153928
• 作为产物：
  描述：

  1-(苯基乙炔基)环戊烷-1-醇 在 吡啶 、 甲酸 、 双氧水 、 三氯氧磷 作用下， 反应 2.0h， 生成 2-(2-phenylacetyl)cyclopentanone
  参考文献：
  名称：

  Untersuchungen �ber die Bildung von 2-Acylcyclopentanonen aus 1-(1-�thynyl)-cyclopentenen und Perameisens�ure

  摘要：

  DOI：

  10.1007/bf01153928

文献信息

• Catalytic Enantioselective Michael Reaction of 1,3-Dicarbonyl Compoundsvia Formation of Chiral Palladium Enolate
  作者：Yoshitaka Hamashima、Daido Hotta、Natsuko Umebayashi、Yasunori Tsuchiya、Takeyuki Suzuki、Mikiko Sodeoka

  DOI：10.1002/adsc.200505199

  日期：2005.10

  catalytic enantioselective Michael reaction has been developed using chiral palladium complexes. Various substrates including β-keto esters and 1,3-diketones reacted with α,β-unsaturated carbonyl compounds to give the corresponding Michael adducts in good yield with up to 99% ee, thereby affording chiral quaternary carbon centers. In these reactions, chiral palladium enolates were generated as key intermediates

  使用手性钯配合物已经开发了有效的催化对映选择性迈克尔反应。包括β-酮酸酯和1,3-二酮在内的各种底物与α，β-不饱和羰基化合物反应，以高达99％ee的高收率得到相应的迈克尔加合物，从而提供了手性季碳中心。在这些反应中，生成了手性钯烯醇盐作为关键中间体，它们与强质子酸协同作用，激活了迈克尔受体，从而促进了CC键形成反应。
• Synthesis of 2-Substituted 1,3-Cycloheptanedione via a Lewis Acid Mediated Ring Expansion Reaction
  作者：Kohei Inomata、Yasuyuki Endo

  DOI：10.3987/com-13-s(s)55

  日期：——

  We have established a new route to provide 2-substituted 1,3-cycloheptanediones via a Lewis acid mediated ring expansion reaction of cyclobutanones as the key step. The ring expansion reactions were mediated by a series of Lewis acids. Among the used Lewis acids, ZnI2 was the most practical mediator. This route has succeeded in providing the title compounds even on a multi-gram scale. During the research, the Baeyer-Villiger oxidation of the cyclobutanones to obtain the new bicyclic lactones was also examined. The regioselective oxidation was observed in the case of chlorinated cyclobutanones.
• Targeting remote axial chirality control of N-(2-tert-butylphenyl)succinimides by means of Michael addition type reactions
  作者：Nicola Di Iorio、Florian Champavert、Agostino Erice、Paolo Righi、Andrea Mazzanti、Giorgio Bencivenni

  DOI：10.1016/j.tet.2016.02.052

  日期：2016.8

  The efficient desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael addition reaction of a series of carbon nucleophiles generating the corresponding axially chiral succinimides in high yields. The use of (DHQD)(2)Pyr as catalyst was fundamental to achieve the remote control of the stereogenic chiral axis with the concurrent construction of adjacent quaternary and tertiary stereocenters. (C) 2016 Elsevier Ltd. All rights reserved.