5-{(hydroxy)[(4-nitrophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione | 1414585-31-1

• 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: 5-{(hydroxy)[(4-nitrophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[hydroxy((4-nitrophenyl)amino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[hydroxy(4-nitrophenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1414585-31-1
• 化学式: C₁₃H₁₂N₂O₇
• 分子量: 308.247
• InChiKey: IODPPEJKAJKNLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  128.0
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-{(hydroxy)[(4-nitrophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以55%的产率得到5-[difluoroboroxy(4-nitrophenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Boron difluoride complexes of carbamoyl Meldrum's acids

  摘要：

  5-[Hydroxy(aryl/alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones react with BF3 center dot Et2O in mild conditions leading to the formation of boron difluoride complexes of carbamoyl Meldrum's acids. The X-ray structure has been obtained for one representative complex. The obtained new compounds are air and moisture stable at standard ambient conditions and easily isolable. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.07.004
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 异氰酸对硝基苯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到5-{(hydroxy)[(4-nitrophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Boron difluoride complexes of carbamoyl Meldrum's acids

  摘要：

  5-[Hydroxy(aryl/alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones react with BF3 center dot Et2O in mild conditions leading to the formation of boron difluoride complexes of carbamoyl Meldrum's acids. The X-ray structure has been obtained for one representative complex. The obtained new compounds are air and moisture stable at standard ambient conditions and easily isolable. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.07.004

文献信息

• Thermal Decomposition of Carbamoyl Meldrum's Acids: A Starting Point for the Preparation of 1,3-Oxazine Derivatives
  作者：Sławomir Makowiec、Ewelina Najda、Karolina Janikowska

  DOI：10.1002/jhet.2028

  日期：2015.1

  The ability to undergo [4 + 2] versus [2 + 2] cycloaddition was under investigation for ketenes thermally generated from carbamoyl Meldrum's acid. Usually, 1,3‐oxazino‐5‐carbamoylo‐4,6‐diones are formed when carbamoyl Meldrum's acid reacts with imine. However, in some cases, a reaction takes an unexpected course, leading to the formation of tetraponerines alkaloids derivatives or cyclic iminoethers.

  对于由氨基甲酰基梅尔德鲁姆酸热生成的乙烯酮，正在研究[4 + 2]与[2 + 2]环加成反应的能力。通常，当氨基甲酰基梅德鲁姆的酸与亚胺反应时，会形成1,3-恶嗪基-5-氨基甲酰基-4,6-二酮。但是，在某些情况下，反应会发生意想不到的过程，导致四皂素生物碱衍生物或环状亚氨基醚的形成。
• A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties
  作者：Anna Zakaszewska、Ewelina Najda-Mocarska、Sławomir Makowiec

  DOI：10.1039/c7nj00445a

  日期：——

  One-pot synthesis of optically active 1,4-disubstituted-3-carbamoyl-azetidinones from 5-[(N-arylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines is achieved via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition. Three possible chiral induction approaches were tested and (R)-(+)-1-phenylethylamine was confirmed as the best chiral auxiliary. Among

  由5-[（N-芳基氨基）（羟基）亚甲基] -2,2-二甲基-1,3-二氧杂-4,6-二酮一锅法合成旋光的1,4-二取代-3-氨基甲酰基-氮杂环丁酮通过氨基甲酰基烯酮的热生成和随后的[2 + 2]环加成反应可得到手性醛亚胺。测试了三种可能的手性诱导方法，并证实（R）-（+）-1-苯基乙胺是最佳手性助剂。在四种可能的非对映异构体中，仅形成了两种，其中一种明显过量。
• Evidence for an umpolung type of [2+2] cycloaddition of 2-carbamoyl ketenes
  作者：Anna Zakaszewska、Ewelina Najda-Mocarska、Sławomir Makowiec

  DOI：10.1039/c7nj00830a

  日期：——

  Ketenes generated during the thermal decomposition of 5-[(N-aryl/alkylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones react with highly electrophilic iminium ions. The initial [2+2] cycloaddition product rearranges to 2-arylidene malonamide. Mechanistic aspects of the process are presented.

  5-[（N-芳基/烷基氨基）（羟基）亚甲基] -2,2-二甲基-1,3-二氧杂-4,6-二酮热分解过程中产生的酮与高亲电性亚胺离子反应。初始的[2 + 2]环加成产物重排为2-亚芳基丙二酰胺。介绍了过程的机械方面。
• Synthesis of 3-Carbamoyl<i>β</i>-Lactams<i>via</i>Manganese(III)-Promoted Cyclization of<i>N</i>-Alkenylmalonamides
  作者：Paweł Punda、Łukasz Ponikiewski、Sławomir Makowiec

  DOI：10.1002/hlca.201200646

  日期：2013.11

  Manganese(III)‐promoted cyclization of N‐alkenylmalonamides (=N‐alkenylpropanediamides) gave 3‐(aryl/(alkylamino)carbonyl) β‐lactams as well as 3‐(aryl/(alkylamino)thiocarbonyl) β‐lactams. The relative configuration of the obtained products was unambiguously determined by X‐ray crystallography. The proposed method is very useful for the one‐pot synthesis of a number of 3‐(aryl/(alkylamino)carbonyl)

  锰（III）促进的N-链烯基丙二酰胺（= N-链烯基丙烷二酰胺）的环化反应生成3-（芳基/（烷基氨基）羰基）β-内酰胺以及3-（芳基/（烷基氨基）硫羰基）β-内酰胺。所得产物的相对构型是由X射线晶体学确定的。所提出的方法对于一锅合成许多3-（芳基/（烷基氨基）羰基）β-内酰胺非常有用，尤其是那些含有氨基（硫羰基）部分的内酰胺，而其他方法无法选择性地获得这些内酰胺。