3-(benzoyl)amino-7,7-dimetyl-5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-one | 125812-05-7

• 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-(benzoyl)amino-7,7-dimetyl-5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-one
• 英文别名: 3-(benzoyl)amino-5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-one；N-(7,7-dimethyl-2,5-dioxo-5,6,7,8-tetrahydro-2H-chromen-3-yl)benzamide；N-(7,7-dimethyl-2,5-dioxo-6,8-dihydrochromen-3-yl)benzamide
• CAS: 125812-05-7
• 化学式: C₁₈H₁₇NO₄
• mdl: MFCD00695483
• 分子量: 311.337
• InChiKey: FKKXTRANJLQERZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  3-(benzoyl)amino-7,7-dimetyl-5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-one 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 3-(benzoylamino)-5,6,7,8-tetrahydro-7,7-dimethyl-2,5-dioxo-1(2H)-quinolineacetate
  参考文献：
  名称：

  Pyrano[3,2-c]azepine, a New Heterocyclic System. A New Approach to Pyrido[3,2-c]azepines

  摘要：

  DOI：

  10.3987/com-89-s8
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 0.42h， 生成 3-(benzoyl)amino-7,7-dimetyl-5-oxo-5,6,7,8-tetrahydro-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Kocevar, Marijan; Polanc, Slovenko; Vercek, Bojan, Liebigs Annalen der Chemie, 1990, # 5, p. 501 - 503

  摘要：

  DOI：

文献信息

• Intermediate products, methods for their preparation and use thereof
  申请人：Personal Chemistry i Uppsala AB

  公开号：EP1367045A1

  公开（公告）日：2003-12-03

  Novel solid supported intermediate products of the general formula coupled to a solid polymeric support through one or both of the R1 groups or through the R4 group which are suitable for synthesis of heterocyclic compounds are disclosed. Methods for preparing such intermediate products are also disclosed and also the use of the intermediate products in simple and fast methods on solid phase for synthesis of heterocycles.

  揭示了一种新型的固体支持中间产物，其一般公式为，通过R1基团中的一个或两个或通过R4基团与固体聚合物支持物耦合，适用于合成杂环化合物。还公开了制备这种中间产物的方法，以及在固相上简单快速地合成杂环化合物的方法中使用这些中间产物。
• Solid Phase Synthesis of Aminopropenonesand Aminopropenoates; Efficient and Versatile Synthons for CombinatorialSynthesis of Heterocycles
  作者：Jacob Westman、Ronny Lundin

  DOI：10.1055/s-2003-39156

  日期：——

  Simple and fast solid phase methods for the synthesis of heterocycles will be described. Two different three-step methods are presented. The first method includes esterifications of N-protected glycine derivatives to a solid support (Merrifield resin), formation of aminopropenoates and subsequent reaction with dinucleophiles. The second method includes methylamination of a Merrifield resin, formation of aminopropenones via in-situ formation of an active intermediate in a three-component reaction and finally treatment with dinucleophiles to form heterocycles. These procedures lead not only to the formation of heterocycles but also to simultaneous intramolecular cleavage of the products from the resin giving the product in pure form in the solution. In addition, the use of microwave dielectric heating enhanced the velocity of all reaction steps and was found to be a very efficient complement to the solid phase synthesis.

  简单快速的固相合成杂环化合物方法将被描述。介绍了两种不同的三步骤方法。第一种方法包括将N-保护的甘氨酸衍生物酯化到固相载体（Merrifield树脂）上，形成氨基丙烯酸酯，随后与双亲核试剂反应。第二种方法包括对Merrifield树脂进行甲基化，通过三组分反应中活性中间体的原位形成来生成氨基丙烯酮，最后通过与双亲核试剂处理形成杂环。这些过程不仅导致了杂环的形成，还导致了产物从树脂上的同时分子内切割，使产物以纯形式存在于溶液中。此外，微波介电加热的使用提高了所有反应步骤的速度，并且被发现是对固相合成非常有效的补充。
• 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。