N-[2-(4'-methoxy)-2-propenyl]phthalimide | 327619-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-[2-(4'-methoxy)-2-propenyl]phthalimide
• 英文别名: 2-(4-methoxyphenyl)-3-N-phthalimido-1-propene；2-[2-(4-Methoxyphenyl)prop-2-enyl]isoindole-1,3-dione
• CAS: 327619-99-8
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: ZMKHIJPUCNCYLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(4'-methoxy)-2-propenyl]phthalimide 在 4-二甲氨基吡啶 、 hydrazine hydrate 、 三乙胺 、 rose bengal 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 40.0h， 生成 5-(4-methoxyphenyl)-5-neopentyl-2-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  烯丙基酰胺与 N-羟基邻苯二甲酰亚胺酯的可见光促进自由基烷基化/环化：恶唑啉的合成

  摘要：

  开发了一种高效的光催化烯丙基酰胺与N-羟基邻苯二甲酰亚胺酯的烷基化/环化反应。该转化利用烷基自由基攻击烯丙基酰胺，并辅以廉价的玫瑰红作为光催化剂，以中等至优异的产率制备一系列烷基取代的恶唑啉。区域选择性高、操作安全、条件温和、底物通用性好，使该协议具有广阔的应用前景。

  DOI：

  10.1016/j.cclet.2021.09.067
• 作为产物：
  描述：

  1-异丙烯基-4-甲氧基苯 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-[2-(4'-methoxy)-2-propenyl]phthalimide
  参考文献：
  名称：

  烯丙基酰胺与 N-羟基邻苯二甲酰亚胺酯的可见光促进自由基烷基化/环化：恶唑啉的合成

  摘要：

  开发了一种高效的光催化烯丙基酰胺与N-羟基邻苯二甲酰亚胺酯的烷基化/环化反应。该转化利用烷基自由基攻击烯丙基酰胺，并辅以廉价的玫瑰红作为光催化剂，以中等至优异的产率制备一系列烷基取代的恶唑啉。区域选择性高、操作安全、条件温和、底物通用性好，使该协议具有广阔的应用前景。

  DOI：

  10.1016/j.cclet.2021.09.067

文献信息

• Regioselective Palladium-Catalyzed Synthesis of <i>β</i>-Arylated Primary Allylamine Equivalents by an Efficient Pd−N Coordination
  作者：Kristofer Olofsson、Helena Sahlin、Mats Larhed、Anders Hallberg

  DOI：10.1021/jo001416y

  日期：2001.1.1

  system, can be performed at the internal, beta-carbon of Boc- and phthalimido-protected allylamines, yielding arylated primary allylamine equivalents. The very high regioselectivity obtained with secondary Boc-protected allylamides is suggested to be caused by an efficient coordination between an anionic nitrogen and palladium. Single-mode microwave irradiation has been utilized to shorten the reaction

  利用芳基三氟甲磺酸酯和钯/ dppf催化体系，可以在Boc和邻苯二甲酰亚胺基保护的烯丙胺的内部β-碳上进行高度区域选择性的Heck芳基化反应，生成芳基化的伯烯丙胺当量。建议用Boc保护的烯丙基仲胺获得很高的区域选择性，这是由于阴离子氮和钯之间的有效配位引起的。利用单模微波辐射可以缩短反应时间，并且在Boc保护的烯丙基酰胺的情况下，可以提高两种贫电子芳基三氟甲磺酸酯的收率。
• Characterization of a Series of 3-Amino-2-phenylpropene Derivatives as Novel Bovine Chromaffin Vesicular Monoamine Transporter Inhibitors
  作者：Rohan P. Perera、D. Shyamali Wimalasena、Kandatege Wimalasena

  DOI：10.1021/jm030004p

  日期：2003.6.1

  A series of 3-amino-2-phenylpropene (APP) derivatives have been synthesized and characterized as novel competitive inhibitors, with K-i values in the muM range, for the bovine chromaffin granule membrane monoamine transporter(s) (bVMAT). Although, these inhibitors are structurally similar to the bVMAT substrate tyramine, none of them were measurably transported into the granule. Structure-activity studies have revealed that, while the 3'- or 4'-OH groups on the aromatic ring enhance the inhibition potency, Me or OMe groups in these positions reduce the inhibition potency. Halogen substitution on the 4'-position of the aromatic ring causes gradual increase of the inhibition potency parallel to the electron donor ability of the halogen. Substituents on the NH2 as well as on the 3-position of the alkyl chain reduce the inhibition potency. Comparative structure-activity analyses of APP derivatives with tyramine and the neurotoxin 1-methyl-4-phenylpyridinium suggest that the flexibility of the side chain and the relative orientation of the NH2 group may be critical for the efficient transport of the substrate through the bVMAT. Comparable bVMAT affinities of these inhibitors to that of DA and other pharmacologically active amines suggest that they are suitable for the structure-activity and mechanistic studies of monoamine transporters and may also be useful in modeling the mechanism of action of amphetamine-related derivatives.
• Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines
  作者：Patrícia Prediger、Laís Ferreira Barbosa、Yves Génisson、Carlos Roque Duarte Correia

  DOI：10.1021/jo201105z

  日期：2011.10.7

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.