N-(4-methoxyphenyl)-N-methyloct-2-ynamide | 1078120-24-7

• 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: N-(4-methoxyphenyl)-N-methyloct-2-ynamide
• CAS: 1078120-24-7
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: MABSAZOVWRGLSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-N-methyloct-2-ynamide 在 copper(l) iodide 、 1-fluoro-2,4,6-trimethylpyridin-1-ium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以32%的产率得到N-methyl-3-iodo-4-pentyl-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
• 作为产物：
  描述：

  在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 20.0h， 生成 N-(4-methoxyphenyl)-N-methyloct-2-ynamide
  参考文献：
  名称：

  Silver-catalyzed carbon–phosphorus functionalization of N-(p-methoxyaryl)propiolamides coupled with dearomatization: access to phosphorylated aza-decenones

  摘要：

  银催化的级联二官能团化反应与去芳构化相结合，成功实现了N-(对甲氧基苯基)丙炔酰胺的转化，并在温和条件下以中等至优异的产率区域选择性地构建了一系列邻近季碳中心的磷酸化氮杂十碳烯酮。

  DOI：

  10.1039/c4cc06923d

文献信息

• 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。
• K₂S₂O₈‐Mediated Access to Alkylsulfonated Spiro[4,5] Trienones from <i>N</i>‐Arylpropiolamides with the Insertion of Sulfur Dioxide
  作者：Xin‐Qian Liu、Peng‐Fei Huang、Bi‐Quan Xiong、Ke‐Wen Tang、Yu Liu

  DOI：10.1002/adsc.202301279

  日期：2024.2.19

  A four‐component reaction of N‐arylpropiolamides, Hantzsch esters, Na₂S₂O₅ and water via a radical cascade cyclization process with the insertion of sulfur dioxide mediated by K₂S₂O₈ is reported. A series of alkylsulfonated spiro[4,5] trienones are prepared up to 86% yield with a good functional group tolerance and substrate applicability. Preliminary mechanism experiments indicate that carbonyl oxygen of spiro[4,5] trienones originated from water.

  摘要 通过 K2S2O8 介导的自由基级联环化过程插入二氧化硫，报告了 N-芳基丙炔酰胺、Hantzsch 酯、Na2S2O5 和水的四组分反应。该研究制备了一系列烷基磺化螺[4,5]三烯酮，收率高达 86%，具有良好的官能团耐受性和底物适用性。初步机理实验表明，螺[4,5] 三烯酮的羰基氧来源于水。