N-(2-iodobenzyl)-N-(4-methoxyphenyl)-3-phenylpropiolamide | 1078120-15-6

• 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-(2-iodobenzyl)-N-(4-methoxyphenyl)-3-phenylpropiolamide
• 英文别名: N-[(2-iodophenyl)methyl]-N-(4-methoxyphenyl)-3-phenylprop-2-ynamide
• CAS: 1078120-15-6
• 化学式: C₂₃H₁₈INO₂
• 分子量: 467.306
• InChiKey: AEDRGHVGHBCJMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  N-(2-iodobenzyl)-N-(4-methoxyphenyl)-3-phenylpropiolamide 在 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以80%的产率得到N-(2-iodobenzyl)-3-bromo-4-phenyl-1-azaspiro[4,5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  Electrophilic ipso-Cyclization of N-(p-Methoxyaryl)propiolamides Involving an Electrophile-Exchange Process

  摘要：

  A novel electrophilic ipso-cyclization involving an electrophile-exchange process has been developed. In the presence of CuX (X = I, Br, SCN) and electrophilic fluoride reagents, a variety of N-(p-methoxyaryl)propiolamides and 4-methoxyphenyl 3-phenylpropiolate were cyclized to selectively afford the corresponding spiro[4.5]decenones in moderate to good yields. It is noteworthy that two azaquaternary tricyclic products were synthesized through a two-step pathway involving an electrophilic ipso-cyclization and then an intramolecular Heck reaction.

  DOI：

  10.1021/jo8018297

文献信息

• Ag-Catalyzed Oxidative <i>ipso</i>-Cyclization via Decarboxylative Acylation/Alkylation: Access to 3-Acyl/Alkyl-spiro[4.5]trienones
  作者：Chada Raji Reddy、Dattahari H. Kolgave、Muppidi Subbarao、Mounika Aila、Santosh Kumar Prajapti

  DOI：10.1021/acs.orglett.0c01588

  日期：2020.7.17

  A strategy to functionalized spiro[4.5]trienones, by domino silver-catalyzed decarboxylative acylation or alkylation/ ipso-cyclization of N-arylpropiolamides with α-keto acids/alkyl carboxylic acids, is presented. This transformation offers a wide range of substituted 3-acyl/alkyl-spiro[4.5]trienones in high yields with a broad substrate scope. The approach was further extended to access fused tricyclic

  的策略官能螺[4.5] trienones，通过多米诺银催化的脱羧酰化或烷基化/烷基本位的-cyclization Ñ与-arylpropiolamidesα酮酸/烷基羧酸，被呈现。该转化以高收率和广泛的底物范围提供了广泛的取代的3-酰基/烷基-螺[4.5]三烯酮。该方法进一步延长到接入稠合三环框架，6,7-二氢-3- ħ吡咯并[2,1- Ĵ ]喹啉-3,9-（5 ħ） -二酮。
• Visible-Light-Mediated ipso-Carbosulfonylation of Alkynes: Synthesis of 3-Sulfonylspiro[4,5]trienones from Propiolamides and Sulfonyl Chlorides under Transition-Metal-Free Conditions
  作者：Yu Liu、Quan Zhou、Qiao-Lin Wang、Bi-Quan Xiong、Pan-Liang Zhang、Chang-An Yang、Yan-Xia Gong、Jing Liao

  DOI：10.1055/s-0037-1609948

  日期：2018.11

  sulfonylation and ipso-cyclization of alkynes. In this transformation, the O atom in the newly generated carbonyl is derived from H2O and it features a broad substrates scope, especially for alkyl propiolamides and aliphatic sulfonyl chlorides.

  已开发出一种高效便捷的合成多种 3-磺酰基螺[4,5] 三烯酮的策略。这种炔烃的同位碳磺酰化在无过渡金属条件下通过可见光催化进行，代表了炔烃的新磺酰化和同位环化。在这种转化中，新生成的羰基中的 O 原子来源于 H2O，它具有广泛的底物范围，特别是对于烷基丙酰胺和脂肪族磺酰氯。
• Visible-light promoted one-pot synthesis of sulfonated spiro[4,5]trienones from propiolamides, anilines and sulfur dioxide under transition metal-free conditions
  作者：Yu Liu、Qiao-Lin Wang、Zan Chen、Quan Zhou、Bi-Quan Xiong、Pan-Liang Zhang、Ke-Wen Tang

  DOI：10.1039/c9cc05949k

  日期：——

  A novel visible-light promoted sulfonylation/ipso-cyclization of N-arylpropiolamides with aromatic amines and DABCO·(SO₂)₂ to synthesize various sulfonated spiro[4,5]trienones is reported.

  报道了一种新颖的可见光促进的N-芳基丙炔酰胺与芳香胺和DABCO·(SO2)2进行磺化/ipso-环化反应，合成各种磺化的螺[4,5]三烯酮。
• 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。