2-methyl-7,11b-dihydro-4H,6H-[1,3]oxazino[2,3-a]isoquinolin-4-one | 256378-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-methyl-7,11b-dihydro-4H,6H-[1,3]oxazino[2,3-a]isoquinolin-4-one
• 英文别名: 2-methyl-7,11b-dihydro-6H-[1,3]oxazino[2,3-a]isoquinolin-4-one
• CAS: 256378-46-8
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: WDXFKUMGRRLLPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-7,11b-dihydro-4H,6H-[1,3]oxazino[2,3-a]isoquinolin-4-one 在 水 作用下， 生成 3,4-二氢异喹啉-1(2H)-酮 、 1-(1-oxo-3,4-dihydroisoquinolin-2-yl)butane-1,3-dione
  参考文献：
  名称：

  Unusual dirhodium tetraacetate catalyzed intramolecular cyclization of isoquinoline diazoamides

  摘要：

  The dirhodium(II) tetraacetate catalyzed decomposition of an isoquinoline diazoamide leads to the unexpected formation of a 1,3-oxazin-4-one ring which is consistent with a rare example of an intramolecular metal-carbene hydride-abstraction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01738-4
• 作为产物：
  描述：

  1-(1,2,3,4-tetrahydroisoquinolin-2-yl)butane-1,3-dione 在 dirhodium tetraacetate 、 对甲苯磺酰叠氮 、 TEA 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 2-methyl-7,11b-dihydro-4H,6H-[1,3]oxazino[2,3-a]isoquinolin-4-one
  参考文献：
  名称：

  Unusual dirhodium tetraacetate catalyzed intramolecular cyclization of isoquinoline diazoamides

  摘要：

  The dirhodium(II) tetraacetate catalyzed decomposition of an isoquinoline diazoamide leads to the unexpected formation of a 1,3-oxazin-4-one ring which is consistent with a rare example of an intramolecular metal-carbene hydride-abstraction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01738-4

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。
• Unusual dirhodium tetraacetate catalyzed intramolecular cyclization of isoquinoline diazoamides
  作者：Giorgio Chelucci、Nicola Culeddu、Antonio Saba、Raffaela Valenti

  DOI：10.1016/s0040-4039(99)01738-4

  日期：1999.11

  The dirhodium(II) tetraacetate catalyzed decomposition of an isoquinoline diazoamide leads to the unexpected formation of a 1,3-oxazin-4-one ring which is consistent with a rare example of an intramolecular metal-carbene hydride-abstraction mechanism. (C) 1999 Elsevier Science Ltd. All rights reserved.