trans-1-<2-(2-Oxopropyl)cyclopentyl>-2-propanone | 136202-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-1-<2-(2-Oxopropyl)cyclopentyl>-2-propanone
• 英文别名: 1,1'-(trans-cyclopentane-1,2-diyl)dipropan-2-one；1-[(1R,2R)-2-(2-oxopropyl)cyclopentyl]propan-2-one
• CAS: 136202-51-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: UHIHKBRKJNYORB-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  戊二醛 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 氯仿 、 苯 为溶剂， 生成 trans-1-<2-(2-Oxopropyl)cyclopentyl>-2-propanone
  参考文献：
  名称：

  Cyclization Reactions of Allylic O-Stannyl Ketyls

  摘要：

  This is a summary of an investigation of the tributyltin hydride-induced cyclization reactions of unsaturated ketones with electronically deficient olefins. This reaction was initiated by an O-stannyl ketyl formed by the addition of a tributyltin radical to a carbonyl, which has both anionic and radical character. The intramolecular coupling produced functionalized cyclopentanes, bearing two synthetically useful carbon appendages. An activating or electron-withdrawing function on the alkene was essential to the cyclization. A dilution study revealed that excellent anti stereoselectivities (>50:1) could be achieved, and this was attributed to a reversible cyclization. Another goal of this study was to separate the radical reactivity from the anionic reactivity of the O-stannyl ketyl by the participation of labile functional groups and external electrophiles. The presence of minor products and enolate-trapping studies demonstrated that the anionic character of the ketyl could be utilized in the form of a tin enolate. This work represents the first free radical- and reagent-based approach to the study of the intramolecular hydrodimerization of activated alkenes.

  DOI：

  10.1021/jo00120a031

文献信息

• Nickel-Catalyzed Organozinc-Promoted Carbocyclizations of Electron-Deficient Alkenes with Tethered Unsaturation
  作者：John Montgomery、Eric Oblinger、Alexey V. Savchenko

  DOI：10.1021/ja9702125

  日期：1997.5.1

  A nickel-catalyzed method for cyclizations of electron-deficient alkenes with tethered unsaturation in the presence of organozincs was developed. Considerable flexibility in the structure of each reactive component was observed. Enones, alkylidene malonates, unsaturated β-ketoesters, and nitroalkenes participated as the electron-deficient alkene; alkynes, enones, 1,3-dienes, and aldehydes participated

  开发了一种镍催化的方法，用于在有机锌存在下对具有束缚不饱和度的缺电子烯烃进行环化。观察到每个反应组件的结构具有相当大的灵活性。烯酮、亚烷基丙二酸酯、不饱和β-酮酯和硝基烯烃作为缺电子烯烃参与；炔烃、烯酮、1,3-二烯和醛作为系链不饱和键参与；以及各种 sp2 和 sp3 杂化的有机锌，包括那些具有 β-氢的有机锌，作为亲核组分参与其中。底物结构、有机锌结构和配体结构都在决定产物选择性方面发挥了重要作用。具有特殊合成意义的是从普通炔烃制备 E 或 Z 三或四取代烯烃的机会。
• The development of a new catalytic process: Bu3SnH-catalyzed reductive cyclization of enals and enones
  作者：David S Hays、Gregory C Fu

  DOI：10.1016/s0040-4020(99)00446-9

  日期：1999.7

  By sequencing two known reactions, a new catalytic carbon-carbon bond-forming process, the Bu3SnH-catalyzed, PhSiH3-mediated reductive cyclization of enals and enones, has been developed. The addition of EtOH to the reactions leads to reproducibly good yields of the cyclized products; a rationale for including this additive is provided.

  通过对两个已知的反应进行测序，已开发出一种新的催化碳-碳键形成过程，即Bu 3 SnH催化的PhSiH 3介导的烯和烯酮的还原环化反应。将EtOH添加到反应中可导致环化产物的可重复生产的良好收率；提供了包括这种添加剂的理由。
• A Cooperative Hydrogen-Bond-Promoted Organophotoredox Catalysis Strategy for Highly Diastereoselective, Reductive Enone Cyclization
  作者：Matthias Neumann、Kirsten Zeitler

  DOI：10.1002/chem.201204573

  日期：2013.5.27

  Metal‐free cooperation: The cooperative combination of Eosin Y as a photoredox catalyst with organocatalytic thiourea allows for the highly diastereoselective construction of trans‐1,2‐cycloalkanes and heterocycles. This new efficient, cooperative organophotoredox/organocatalysis protocol presents a valuable alternative to metal‐based photoredox approaches and is the first example of combining photoredox

  无金属配合：曙红Y作为一种光氧化还原催化剂与有机催化硫脲的配合组合，可实现对反式1,2-环烷烃和杂环的高度非对映选择性。这种新的高效，协作的有机光氧化还原/有机催化方案为基于金属的光氧化还原方法提供了一种有价值的替代方法，并且是将光氧化还原与氢键催化结合使用的第一个示例（参见方案）。
• Organotin Hydride Catalyzed Carbon−Carbon Bond Formation:  Radical-Mediated Reductive Cyclization of Enals and Enones
  作者：David S. Hays、Gregory C. Fu

  DOI：10.1021/jo951827s

  日期：1996.1.1
• Enholm, Eric J.; Kinter, Kevin S., Journal of the American Chemical Society, 1991, vol. 113, # 20, p. 7784 - 7785
  作者：Enholm, Eric J.、Kinter, Kevin S.

  DOI：——

  日期：——