2-oxo-cyclopentanecarboxylic acid-[1]naphthylamide | 51089-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-oxo-cyclopentanecarboxylic acid-[1]naphthylamide
• 英文别名: 2-Oxo-cyclopentancarbonsaeure-[1]naphthylamid；2-(N-α-Naphthylcarbamoyl)cyclopentan-1-on；2-Oxo-cyclopentancarbonsaeure-naphth-1-ylamid；N-naphthalen-1-yl-2-oxocyclopentane-1-carboxamide
• CAS: 51089-07-7
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: JXVKISRLZUSRSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  526.6±43.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-oxo-cyclopentanecarboxylic acid-[1]naphthylamide 在 硫酸 、 三氯氧磷 作用下， 生成 12-Chloro-15,16-dihydro-11-azacyclopentaphenanthren
  参考文献：
  名称：

  40.合成氮杂类固醇的实验。第一部分

  摘要：

  DOI：

  10.1039/jr9530000192
• 作为产物：
  描述：

  2-Trimethylsilanyloxy-cyclopent-1-enecarboxylic acid naphthalen-1-ylamide 以97%的产率得到
  参考文献：
  名称：

  INABA S.; OJIMA I.; YOSHIDA K.; NAGAI M., J. ORGANOMETAL. CHEM., 1979, 164, NO 2, 123-134

  摘要：

  DOI：

文献信息

• Origin of the Enantioselectivity in Organocatalytic Michael Additions of β-Ketoamides to α,β-Unsaturated Carbonyls: A Combined Experimental, Spectroscopic and Theoretical Study
  作者：Adrien Quintard、Diana Cheshmedzhieva、Maria del Mar Sanchez Duque、Anouk Gaudel-Siri、Jean-Valère Naubron、Yves Génisson、Jean-Christophe Plaquevent、Xavier Bugaut、Jean Rodriguez、Thierry Constantieux

  DOI：10.1002/chem.201404481

  日期：2015.1.7

  The organocatalytic enantioselective conjugate addition of secondary β‐ketoamides to α,β‐unsaturated carbonyl compounds is reported. Use of bifunctional Takemoto’s thiourea catalyst allows enantiocontrol of the reaction leading either to simple Michael adducts or spirocyclic aminals in up to 99 % ee. The origin of the enantioselectivity has been rationalised based on combined DFT calculations and kinetic

  据报道，β-酮酰胺仲胺向α，β-不饱和羰基化合物的有机催化对映选择性共轭加成反应。使用双功能Takemoto's硫脲催化剂可以对反应进行对映体控制，从而导致简单的Michael加合物或高达99％ee的螺环缩醛 。基于组合的DFT计算和动力学分析，对映选择性的起源已经合理化。这项研究提供了对反应机理的更深入的了解，其中涉及仲酰胺质子的主要作用，并阐明了底物与催化剂之间发生的复杂相互作用。
• Construction of Complex 1,3-Cyclohexadienes via Phosphine-Catalyzed (4 + 2) Annulations of δ-Acetoxy Allenoates and Ketones
  作者：Yuwen Zhang、Xiaofeng Tong

  DOI：10.1021/acs.orglett.7b02787

  日期：2017.10.6

  The phosphine-catalyzed substrate-dependent (4 + 2) annulations of δ-acetoxy allenoates with ketones is described. Allenoates 1 with an alkyl substituent at δC are able to react with cyclic 1,3-diketones 2, wherein the δC is attacked by the methenyl carbon of 2 while the αC attacks the ketone of 2. Allenoates 5 with an aryl group at δC is poised to react with cyclic β-carbonyl amides 6, in which the

  描述了膦催化的δ-乙酰氧基烯丙酸酯与酮的底物依赖性（4 + 2）环。在δC处具有烷基取代基的脲基甲酸酯1能够与环状1,3-二酮2反应，其中δC受到2的亚甲基碳的攻击，而αC侵袭2的酮。可以与环状β-羰基酰胺6反应，其中αC受到6的亚甲基碳的攻击，而δC经过1,2加成至6的酮。
• A Cooperative Participation of the Amido Group in the Organocatalytic Construction of All-Carbon Quaternary Stereocenters by Michael Addition with β-Ketoamides
  作者：Maria del Mar Sanchez Duque、Olivier Baslé、Nicolas Isambert、Anouk Gaudel-Siri、Yves Génisson、Jean-Christophe Plaquevent、Jean Rodriguez、Thierry Constantieux

  DOI：10.1021/ol200924e

  日期：2011.7.1

  The secondary amido group of a-substituted beta-ketoamides plays a crucial role in the control of the reactivity and spatial arrangement (selectivity) in the organocatalyzed Michael addition to unsaturated carbonyls. This results in an unprecedented activation mode of substrates through H-bonding interactions allowing the construction of enantiomerically enriched functionalized all-carbon quaternary centers and spiroaminals of high synthetic potential.
• Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Functionalized Cyclohexanes
  作者：Xavier Bugaut、Damien Bonne、Wilfried Raimondi、Maria Sanchez Duque、Sébastien Goudedranche、Adrien Quintard、Thierry Constantieux、Jean Rodriguez

  DOI：10.1055/s-0033-1338844

  日期：——

  Several reactive sites of 1,2- and 1,3-ketoamides were successively exploited in two complementary domino transformations for the synthesis of polysubstituted monocyclic or bridged bicyclic cyclohexanes, with the creation of up to six stereogenic centers. In both cases, a chiral bifunctional thiourea organocatalyst allowed efficient control of chirality in the final carbocycle.