(Z)-N-(4-phenylbut-3-enyl)phthalimide | 74591-93-8

• 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: (Z)-N-(4-phenylbut-3-enyl)phthalimide
• 英文别名: (Z)-N-(4-phenyl-3-butenyl)phthalimide；2-[(Z)-4-phenylbut-3-enyl]isoindole-1,3-dione
• CAS: 74591-93-8
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: DORKDNPQZDMUGX-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 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：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-(4-phenylbut-3-enyl)phthalimide 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 N-acetyl-(Z)-4-phenyl-but-3-enylamine
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines

  摘要：

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.

  DOI：

  10.1021/ol025659j
• 作为产物：
  描述：

  N-(3-溴丙基)苯二胺 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 44.0h， 生成 (Z)-N-(4-phenylbut-3-enyl)phthalimide
  参考文献：
  名称：

  Preparation and stereochemistry of 4-aryl-3-butenylamines. A novel synthesis of an oxazolo[2,3-a]isoindole

  摘要：

  DOI：

  10.1021/jo01308a022

文献信息

• Palladium-catalysed anti-Markovnikov selective oxidative amination
  作者：Daniel G. Kohler、Samuel N. Gockel、Jennifer L. Kennemur、Peter J. Waller、Kami L. Hull

  DOI：10.1038/nchem.2904

  日期：2018.3

  functional group intolerance. As such, a general approach to the synthesis of nitrogen-containing compounds from readily available and benign starting materials is highly desirable. Here we present a palladium-catalysed oxidative amination reaction in which the addition of the nitrogen occurs at the less-substituted carbon of a double bond, in what is known as anti-Markovnikov selectivity. Alkenes are shown

  近年来，胺和其他含氮基序的合成一直是有机化学研究的一个主要领域，因为它们广泛地存在于生物活性分子中。当前的策略依赖于多步骤方法，并要求在形成碳氮键之前先活化一种反应物。这导致反应效率低下和官能团不耐受。因此，非常需要从容易获得的和良性的起始原料合成含氮化合物的一般方法。这里，我们提出一个钯催化的胺化的氧化反应，其中在添加氮的发生在双键的较少取代的碳，在所谓的抗马尔可夫尼科夫选择性。已显示烯烃在palladate催化剂的存在下与酰亚胺反应，以通过反式-氨基palladation生成末端酰亚胺。随后，发生烯烃异构化以提供热力学上有利的产物。既报告了转换范围，也报告了机制研究。
• Convenient Route to Primary (<i>Z</i>)-Allyl Amines and Homologs
  作者：Alejandra Gerpe、Mariela Bollini、Mercedes González、Hugo Cerecetto

  DOI：10.1080/00397910802369596

  日期：2008.12.16

  A convenient two-step procedure for the synthesis of primary (Z)-allyl amines, (Z)-homoallyl amines [(Z)-but-3-enylamines], and (Z)-pent-4-enylamines using the Wittig reaction was achieved. The use of nonstabilized ylides from triphenylphosphonium salt, potassium salt, and apolar solvent produced (Z/E)geometric isomer ratios generally greater than 1.6. The amine moiety was masked using a phtalimide group that was removed successfully in the last step of the process in two different conditions, NH2NH2/EtOH/rt or CH3NH2/EtOH/rt. However, in some cases, reduction of the C=C double bond in the deprotection with hydrazine was concomitantly observed.
• OLSEN D. K.; TORIAN B. E.; MORGAN C. D.; BRAUN L. L., J. ORG. CHEM., 1980, 45, NO 20, 4049-4052
  作者：OLSEN D. K.、 TORIAN B. E.、 MORGAN C. D.、 BRAUN L. L.

  DOI：——

  日期：——
• MCEWEN, W. E.;COONEY, J. V., J. ORG. CHEM., 1983, 48, N 7, 983-987
  作者：MCEWEN, W. E.、COONEY, J. V.

  DOI：——

  日期：——
• Brønsted Acid-Catalyzed Intramolecular Hydroamination of Protected Alkenylamines. Synthesis of Pyrrolidines and Piperidines
  作者：Björn Schlummer、John F. Hartwig

  DOI：10.1021/ol025659j

  日期：2002.5.1

  [GRAPHIC]The cyclization of aminoalkenes bearing an electron-withdrawing group on the nitrogen atom was catalyzed by triflic or sulfuric acid in toluene. Pyrrolidines and piperidines were formed in excellent yields. N-Phenylanilides also underwent cyclization to form gamma-lactams.