3-(4-methoxybenzoyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione | 1607433-07-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-methoxybenzoyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 英文别名: 3-(4-Methoxybenzoyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
• CAS: 1607433-07-7
• 化学式: C₂₄H₁₉NO₄
• 分子量: 385.419
• InChiKey: ZOWJRTBMIOSYSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-methoxyphenyl)-N-methyl-3-phenylpropiolamide 、 对甲氧基苯乙醛酸 在 dipotassium peroxodisulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以85%的产率得到3-(4-methoxybenzoyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  Metal-free spirocyclization of N-arylpropiolamides with glyoxylic acids: access to complex azaspiro-fused tricycles

  摘要：

  一种高效的K₂S₂O₈介导的氧化级联螺环化反应被证明可用于构建氮杂螺[4,5]-三烯酮和复杂的氮杂螺合并结构。

  DOI：

  10.1039/d0cc04800c

文献信息

• Visible-Light-Mediated <i>Ipso</i>-Carboacylation of Alkynes: Synthesis of 3-Acylspiro[4,5]trienones from <i>N</i>-(<i>p</i>-Methoxyaryl)propiolamides and Acyl Chlorides
  作者：Yu Liu、Qiao-Lin Wang、Cong-Shan Zhou、Bi-Quan Xiong、Pan-Liang Zhang、Chang-an Yang、Ke-Wen Tang

  DOI：10.1021/acs.joc.7b03104

  日期：2018.2.16

  A novel visible-light-mediated ipso-carboacylation of N-(p-methoxyaryl)propiolamides with acyl chloride has been established for the synthesis of diverse 3-acylspiro[4,5]trienones with high selectivity and efficiency. This method represents a new difunctionalization of alkynes through cross coupling of the acyl chloride C–Cl bonds with an ipso-aromatic carbon by simultaneously forming two new carbon–carbon

  一种新颖的可见光介导的本位的-carboacylation ñ - （p -methoxyaryl）与酰氯propiolamides成立已经多样化3- acylspiro的合成[4,5] trienones以高选择性和效率。该方法通过同时形成两个新的碳-碳键和一个碳-氧双键，将酰氯C-Cl键与ipso-芳族碳交叉偶联，代表了炔烃的新双官能团。
• Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones
  作者：Pu Chen、Jun Xie、Zan Chen、Bi‐Quan Xiong、Yu Liu、Chang‐An Yang、Ke‐Wen Tang

  DOI：10.1002/adsc.202100852

  日期：2021.9.21

  A nitrogen-centered radical strategy for the preparation of 3-acylated spiro[4,5]trienones via visible-light-mediated acylation/ipso-cyclization of alkynes with acyl oxime esters is reported. The alkyl- and aryl-substituted acyl radicals, which generate from the cleavage of carbon-carbon σ-bonds in acyl oxime esters via nitrogen-centered radical pathway, attack the carbon-carbon triple bonds in propiolamides

  为3-酰化螺的制备氮为中心的自由基的策略[4,5] trienones经由可见光介导的酰化/本位与酰基肟酯炔-cyclization报道。所述烷基和芳基取代的酰基的基团，其由碳-碳裂解生成σ -键在酰基肟酯经由氮为中心的自由基途径，攻击在propiolamides碳-碳三键，并且然后经受本位-cyclization。该方法为构建3-酰基取代的螺[4,5]三烯酮提供了一种方法，可以将芳基或烷基取代的酰基引入螺[4,5]三烯酮骨架中。
• Metal-Free Oxidative <i>Ipso</i>-Carboacylation of Alkynes: Synthesis of 3-Acylspiro[4,5]trienones from <i>N</i>-Arylpropiolamides and Aldehydes
  作者：Xuan-Hui Ouyang、Ren-Jie Song、Yang Li、Bang Liu、Jin-Heng Li

  DOI：10.1021/jo5005982

  日期：2014.5.16

  A general and metal-free radical route to synthesis of 3-acylspiro[4,5]trienones is established that utilizes TBHP (tert-butyl hydrogenperwdde) as an oxidation and a reaction partner to trigger the oxidative ipso-carboacylation of N-arylpropiolamides with aldehydes. This method offers a new difunctionalization of alkynes through oxidative cross coupling of the aldehyde C(sp(2))-H bond with an ipso-aromatic carbon.
• Metal-free spirocyclization of <i>N</i>-arylpropiolamides with glyoxylic acids: access to complex azaspiro-fused tricycles
  作者：Akshay M. Nair、Anand H. Shinde、Shreemoyee Kumar、Chandra M. R. Volla

  DOI：10.1039/d0cc04800c

  日期：——

  An efficient K₂S₂O₈-mediated oxidative cascade spirocyclization of N-arylpropiolamides with aryl glyoxylic acids was demonstrated for constructing azaspiro[4,5]-trienones and complex azaspiro-fused architectures.

  一种高效的K₂S₂O₈介导的氧化级联螺环化反应被证明可用于构建氮杂螺[4,5]-三烯酮和复杂的氮杂螺合并结构。