3-Benzoylamino-5,6,7,8-tetrahydro-cumarin | 92963-44-5

• 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: 3-Benzoylamino-5,6,7,8-tetrahydro-cumarin
• 英文别名: 3-benzoylamino-5,6,7,8-tetrahydro-chromen-2-one；Benzamide, N-(5,6,7,8-tetrahydro-2-oxo-2H-1-benzopyran-3-yl)-；N-(2-oxo-5,6,7,8-tetrahydrochromen-3-yl)benzamide
• CAS: 92963-44-5
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: XQHPJJWTTDYOJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Benzoylamino-5,6,7,8-tetrahydro-cumarin 在 氧气 、 甲烷 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以12%的产率得到3-benzamidocoumarin
  参考文献：
  名称：

  Oxydehydrogenative aromatization of fused 3-aminopyran-2-ones on carbon surfaces: a simple approach towards 3-amino-5-hydroxycoumarin derivatives

  摘要：

  Aromatization of selected 3-acylamino-5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones, yielding the corresponding 3-acylamino-5-hydroxycoumarins, was achieved by dehydrogenation with molecular oxygen in the presence of activated carbon. The use of nonpolar solvents and high temperatures was crucial for attaining satisfactory conversions. The 3-benzoylamino-5,6,7,8-tetrahydrocoumarin without a 5-keto group and the 8-oxo analogue as well as the 5-oxo-5,6,7,8-tetrahydrocoumarins containing a free 3-amino group were less efficiently aromatized..

  DOI：

  10.1007/s00706-014-1227-4

文献信息

• Diels−Alder Reactions of Fused Pyran-2-ones with Maleimides:  Efficient Syntheses of Benz[<i>e</i>]isoindoles and Related Systems
  作者：Krištof Kranjc、Slovenko Polanc、Marijan Kočevar

  DOI：10.1021/ol034852q

  日期：2003.8.1

  N-substituted maleimides (2a-c) leading to fused isoindole derivatives (5a-n, 7) or, in a few cases, to bridged double cycloadducts (fused bicyclo[2.2.2]octene derivatives) (6a-f) is presented. When X = CO, the first efficient, substituent-driven aromatization of an intermediary-formed cycloadduct was observed, resulting in substituted benz[e]isoindoles (5a-k). The same type of aromatization can also

  [反应：参见文本]一些取代的5,6,7,8-四氢-2H-1-苯并吡喃-2-酮（1a-f）与N-取代的马来酰亚胺（2a-c）的Diels-Alder反应导致提出了稠合的异吲哚衍生物（5a-n，7），或在少数情况下与桥连的双环加合物（稠合的双环[2.2.2]辛烯衍生物）（6a-f）。当X = CO时，观察到中间体形成的环加合物的第一个有效的，取代基驱动的芳构化，生成取代的苯并[e]异吲哚（5a-k）。在Rh / C前所未有的催化作用下，也可以实现相同类型的芳构化。
• Effect of Ring Size on the<i>Exo</i>/<i>Endo</i>Selectivity of a Thermal Double Cycloaddition of Fused Pyran-2-ones
  作者：Kris̆tof Kranjc、Franc Perdih、Marijan Koc̆evar

  DOI：10.1021/jo9011199

  日期：2009.8.21

  A study of an unusual effect of the size of the ring fused to 2H-pyran-2-ones on the exo/endo selectivity of a thermal double cycloaddition of N-substituted maleimides or maleic anhydride yielding bicyclo[2.2.2]octene derivatives is presented. With subtle variations of starting compounds and reaction conditions exclusively exo,exo or exo,endo products can be prepared.

  研究2 H-吡喃-2-酮稠合的环的大小对N-取代的马来酰亚胺或马来酸酐热双环加成反应生成双环[2.2.2]辛烯衍生物的外/内选择性的异常影响被表达。用的起始化合物和反应条件的细微变化专门外，外切或外切，远藤产品可以制备。
• Intensification of a Reaction by the Addition of a Minor Amount of Solvent: Diels-Alder Reaction of 2H-Pyran-2-ones with Alkynes
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1135/cccc20060667

  日期：——

  Diels-Alder transformation of substituted 3-benzoylamino-2H-pyran-2-ones 1 with a variety of alkynes 2 under microwave (MW) irradiation in a closed system can be intensified in a novel way by addition of a minor amount of butan-1-ol. When the reagents are not volatile under the used conditions, the reactions do not seem to be influenced by the addition of butan-1-ol, as demonstrated by the cycloaddition of a fused 2H-pyran-2-one 5 with N-ethylmaleimide (6) giving adduct 7.

  用微波（MW）辐射在封闭系统中对取代的3-苯甲酰氨基-2H-吡喃-2-酮 1 与多种炔烃 2 进行 Diels-Alder 变换，通过添加少量丁醇可以以一种新颖的方式加强反应。当试剂在所用条件下不挥发时，添加丁醇似乎不会影响反应，这由融合的2H-吡喃-2-酮 5 与 N-乙基马来酰亚胺 (6) 发生的环加成反应，生成产物 7 所证明。
• Kranjc, Kristof; Leban, Ivan; Polanc, Slovenko, Heterocycles, 2002, vol. 58, p. 183 - 190
  作者：Kranjc, Kristof、Leban, Ivan、Polanc, Slovenko、Kocevar, Marijan

  DOI：——

  日期：——
• Oxydehydrogenative aromatization of fused 3-aminopyran-2-ones on carbon surfaces: a simple approach towards 3-amino-5-hydroxycoumarin derivatives
  作者：Bogdan Štefane、Franc Požgan

  DOI：10.1007/s00706-014-1227-4

  日期：2014.8

  Aromatization of selected 3-acylamino-5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones, yielding the corresponding 3-acylamino-5-hydroxycoumarins, was achieved by dehydrogenation with molecular oxygen in the presence of activated carbon. The use of nonpolar solvents and high temperatures was crucial for attaining satisfactory conversions. The 3-benzoylamino-5,6,7,8-tetrahydrocoumarin without a 5-keto group and the 8-oxo analogue as well as the 5-oxo-5,6,7,8-tetrahydrocoumarins containing a free 3-amino group were less efficiently aromatized..