2-methyl-4-N-(4-methoxyphenyl)amino-4-(2-furyl)butene-1 | 433972-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methyl-4-N-(4-methoxyphenyl)amino-4-(2-furyl)butene-1
• 英文别名: N-[1-(furan-2-yl)-3-methylbut-3-en-1-yl]-4-methoxyaniline；N-[1-(furan-2-yl)-3-methylbut-3-enyl]-4-methoxyaniline
• CAS: 433972-28-2
• 化学式: C₁₆H₁₉NO₂
• mdl: MFCD03075602
• 分子量: 257.332
• InChiKey: XCCWMCURSMVEQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-4-N-(4-methoxyphenyl)amino-4-(2-furyl)butene-1 在 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 sodium iodide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 25.0h， 生成 (3S,5R)-5-(furan-2-yl)-3-(iodomethyl)-1-(4-methoxyphenyl)-3-methylpyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of substituted γ-lactam via Pd(0)-catalyzed cyclization of alkene-tethered carbamoyl chloride

  摘要：

  Pd(0)-catalyzed carboiodonation of but-3-enylcarbamic chloride has been developed with NaI as additive, which provides a ready access to substituted gamma-lactam bearing an alkyl iodide group. This reaction features alkyl iodide reductive elimination as a key step in catalytic cycle, indicating the crucial role of additive NaI. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.019
• 作为产物：
  描述：

  1-(呋喃-2-基)-N-(4-甲氧基苯基)甲亚胺 、 2-Methylallylmagnesium Chloride 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-methyl-4-N-(4-methoxyphenyl)amino-4-(2-furyl)butene-1
  参考文献：
  名称：

  Synthesis of substituted γ-lactam via Pd(0)-catalyzed cyclization of alkene-tethered carbamoyl chloride

  摘要：

  Pd(0)-catalyzed carboiodonation of but-3-enylcarbamic chloride has been developed with NaI as additive, which provides a ready access to substituted gamma-lactam bearing an alkyl iodide group. This reaction features alkyl iodide reductive elimination as a key step in catalytic cycle, indicating the crucial role of additive NaI. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.019

文献信息

• Intramolecular [4+2] cycloaddition of furfurylsubstituted homoallylamines to allylhalides, acryloyl chloride and maleic anhydride
  作者：Alexey V. Varlamov、Ekaterina V. Boltukhina、Fedor I. Zubkov、Eugenia V. Nikitina、Konstantin F. Turchin

  DOI：10.1002/jhet.5570430611

  日期：2006.11

  chloride or allylhalides provided 3-aza-10-oxatricyclo[5.2.1.01,5]decenes. The tricycles are formed via an initial amide formation followed by a stereoselective exo-IMDAF (Intramolecular Diels-Alder of Furan). In case of competing cycloaddition (for compounds possessing two furan or two dienophilic moieties) the most substituted fivemembered cycle is preferably annulated. Refluxing of 4-R-4-furfurylaminobut-1-enes

  的4-（呋喃基-2-基）-4-酰化ř -aminobut -1-烯烃和4- [R -4- furfurylaminobut -1-烯烃与马来酸酐，丙烯酰氯或allylhalides提供3-氮杂-10-氧杂三环[5.2。 1.0 1,5 ]癸烯。三环化合物是通过最初的酰胺形成，然后是立体选择性的exo -IMDAF（分子内Diels-Alder of Furan）形成的。在竞争性环加成的情况下（对于具有两个呋喃或两个双亲二烯基的化合物），最好对最取代的五元环进行环化。4- R -4-糠基氨基丁-1-烯在乙酸酐中的回流导致exo -3-aza-11-oxatricyclo [6.2.1.0 1,6具有伪赤道取代基R -4的十一碳烯。在90-110°C下用PPA处理3-氮杂-10-氧杂三环[5.2.1.0 1,5 ]癸烯可促进环醚的打开，芳构化和分子内环化反应顺序，从而得到相应的四环化合物-四氢异吲哚并[2
• New synthetic approach to substituted isoindolo[2,1-a]quinoline carboxylic acids via intramolecular Diels–Alder reaction of 4-(N-furyl-2)-4-arylaminobutenes-1 with maleic anhydride
  作者：Fedor I. Zubkov、Ekaterina V. Boltukhina、Konstantin F. Turchin、Roman S. Borisov、Alexey V. Varlamov

  DOI：10.1016/j.tet.2005.02.017

  日期：2005.4

  Acylation of substituted 4-(furyl-2)-4-arylaminobut-1-enes with maleic anhydride provided 2-allyl-6-carboxy-4-oxo-3-aza-10-oxatricyclo[5.2.1.01,5]dec-8-enes in high yield under mild reaction conditions. The Diels–Alder adducts are formed via an initial amide formation followed by a stereoselective intramolecular [4+2] exo-cycloaddition reaction. Treatment of the tricyclic compounds with phosphoric

  用马来酸酐酰化取代的4-（呋喃基-2）-4-芳基氨基丁-1-烯，得到2-烯丙基-6-羧基-4-氧代-3-氧杂-3-氮杂-10-氧杂三环[5.2.1.0 1,5 ] dec在温和的反应条件下，高产率的-8-烯。的狄尔斯-阿德耳加合物通过初始酰胺形成随后是立体选择性的分子内[4 + 2]形成外型-环反应。在高温（70–120°C）下用磷酸处理三环化合物可促进环醚的打开，分子内环化和芳构化，从而得到相应的四环化合物5,6,6a，11-四氢-10-羧基异吲哚[2， 1- a ]喹啉，产量中等。还讨论了酸和反应温度对环化反应的影响。
• A general strategy for the synthesis of oxoisoindolo[2,1-a]quinoline derivatives: the first efficient synthesis of 5,6,6a,11-tetrahydro-11-oxoisoindolo[2,1-a]quinoline-10-carboxylic acids
  作者：Alexey V. Varlamov、Fedor I. Zubkov、Ekaterina V. Boltukhina、Natalya V. Sidorenko、Roman S. Borisov

  DOI：10.1016/s0040-4039(03)00705-6

  日期：2003.4

  An efficient two-step synthesis of new isoindolo[2,1-a]quinoline-10-carboxylic acids via [4+2] cycloaddition of the 4-alpha-furyl-4-N-arylaminobut-1-enes and maleic anhydride is described. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of substituted γ-lactam via Pd(0)-catalyzed cyclization of alkene-tethered carbamoyl chloride
  作者：Chen Chen、Jian Hu、Jianhua Su、Xiaofeng Tong

  DOI：10.1016/j.tetlet.2014.04.019

  日期：2014.5

  Pd(0)-catalyzed carboiodonation of but-3-enylcarbamic chloride has been developed with NaI as additive, which provides a ready access to substituted gamma-lactam bearing an alkyl iodide group. This reaction features alkyl iodide reductive elimination as a key step in catalytic cycle, indicating the crucial role of additive NaI. (C) 2014 Elsevier Ltd. All rights reserved.