N-(5,6,7,8-tetrahydro-7-methyl-2,5-dioxo-2H-1-benzopyran-3-yl)benzamide | 125812-06-8

• 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: N-(5,6,7,8-tetrahydro-7-methyl-2,5-dioxo-2H-1-benzopyran-3-yl)benzamide
• 英文别名: N-(7-methyl-2,5-dioxo-7,8-dihydro-6H-chromen-3-yl)benzamide
• CAS: 125812-06-8
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: QMNLTOHGWKHSPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5,6,7,8-tetrahydro-7-methyl-2,5-dioxo-2H-1-benzopyran-3-yl)benzamide 在 氧气 、 甲烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以46%的产率得到N-(5-hydroxy-7-methyl-2-oxo-2H-chromen-3-yl)-benzamide
  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
• 作为产物：
  描述：

  (Z)-4-(ethoxymethylene)-2-phenyloxazol-5(4H)-one 、 5-甲基环己烷-1,3-二酮 以 溶剂黄146 为溶剂， 反应 7.5h， 以35%的产率得到N-(5,6,7,8-tetrahydro-7-methyl-2,5-dioxo-2H-1-benzopyran-3-yl)benzamide
  参考文献：
  名称：

  Kepe, Vladimir; Kocevar, Marijan; Petric, Andrej, Heterocycles, 1992, vol. 33, # 2, p. 843 - 849

  摘要：

  DOI：

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。
• Selective and efficient transformation of 5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones with hydrazines to 5-hydrazono-2H-1-benzopyran-2-ones and quinoline-2,5-diones. Extension to related systems
  作者：Polonca Trebše、Slovenko Polanc、Marijan Kočevar、Tomaž Šolmajer、Simona GoličGrdadolnik

  DOI：10.1016/s0040-4020(96)01050-2

  日期：1997.1

  derivative 14 with hydrazides, phenylhydrazines and heterocyclic hydrazines as nitrogen-containing nucleophiles were investigated. The benzopyran-2,5-diones were converted to the corresponding 5-hydrazono-2H-1-benzopyrans of type a and further to quinolines of type b. In the 2H-pyran-2-one series the corresponding hydrazone 15 and pyrazole 16 were obtained. In some cases, using interatomic distances

  5,6,7,8-四氢-2 H -1-苯并吡喃-2,5-二酮1-3和5-乙酰基2 H-吡喃-2-酮衍生物14的高选择性转化反应，包括酰肼，苯肼和杂环研究了肼作为含氮亲核试剂。将苯并吡喃-2，5-二酮转化为相应的类型a的5-肼基-2 H -1-苯并吡喃，并进一步转化为类型b的喹啉。在2 H-吡喃-2-酮系列中，相应的15和吡唑16获得了。在某些情况下，使用从NOESY光谱获得的原子间距离，进行构象分析并计算形成热。
• Selective synthesis of some 5-hydrazono-5,6,7,8-tetrahydro-2<i>H</i>-1-benzopyran-2-ones
  作者：Polonca Trebše、Boris Recelj、Marijan Kočevar、Slovenko Polanc

  DOI：10.1002/jhet.5570340425

  日期：1997.7

  A simple, highly selective transformation of 5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones 1–3 and 14 with some phenylhydrazines and heterocyclic hydrazines to 5-hydrazono-2H-1-benzopyran-2-ones 4–12 and 15–16 is described. Under more severe conditions the hydrazonoquinoline derivative 17 was obtained from the benzopyran derivative 3 and Phenylhydrazine.

  简单，高选择性地将5,6,7,8-tetrahydro-2 H -1-苯并吡喃-2,5-二酮1-3和14与一些苯肼和杂环肼一起转化为5-hydrazono-2 H -1-描述了苯并吡喃-2-酮4-12和15-16。在更严格的条件下，从苯并吡喃衍生物3和苯肼获得了肼基喹啉衍生物17。
• Diels–Alder reaction of fused pyran-2-ones with ethyl vinyl ether
  作者：Amadej Juranovič、Krištof Kranjc、Slovenko Polanc、Franc Perdih、Marijan Kočevar

  DOI：10.1007/s00706-012-0734-4

  日期：2012.5

  AbstractEthyl vinyl ether was found to be an appropriate synthetic equivalent of acetylene for a set of Diels–Alder reactions with fused pyran-2-ones that yield fused carbocyclic systems. Transformations were conducted under microwave irradiation with DABCO (as a catalyst for the elimination of ethanol) and with n-butanol as the additive. A single-crystal X-ray diffraction structure is presented for

  摘要发现乙基乙烯基醚是乙炔的适当合成当量，适用于与稠合吡喃-2-酮的一系列Diels-Alder反应，产生稠合碳环系统。在微波辐射下，用DABCO（作为消除乙醇的催化剂）和正丁醇作为添加剂进行转化。提出了N-（5,6,7,8-四氢-6-甲基-8-氧代萘-2-基）苯甲酰胺的单晶X射线衍射结构。 图形概要
• Regioselectivity in the Schmidt Reaction: First Synthesis of Pyrano[3,2-b]azepines
  作者：Marijan Kočevar、Franc Pozgan、Slovenko Polanc

  DOI：10.3987/com-01-s(k)53

  日期：——

  The Schmidt reaction of 5,6,7,8-tetrahydro-2H-1-benzopyran-2-ones (1) has been investigated. Derivatives of pyrano[3,2-c]azepines (2) and isomeric pyrano[3,2-b]azepines (3) were isolated by the application of trimethylsilyl azide or sodium azide in a methylene chloride or a chloroform solution in the presence of sulfuric acid At low temperature products (2) were almost sole products, while at higher

  已经研究了 5,6,7,8-四氢-2H-1-苯并吡喃-2-酮 (1) 的施密特反应。吡喃并[3,2-c]氮杂 (2) 和异构体吡喃并[3,2-b]氮杂 (3) 的衍生物通过在二氯甲烷或氯仿溶液中应用三甲基甲硅烷基叠氮化物或叠氮化钠在存在的情况下进行分离硫酸在低温下的产物 (2) 几乎是唯一的产物，而在高温下的衍生物 (3) 也以合理的收率被分离出来。吡喃并[3,2-c]吡啶(5)的衍生物可以使用相同的方法由环戊-[b]吡喃-2,5-二酮(4)制备。