2-(4-苯基丁-3-烯基)异吲哚-1,3-二酮 | 143741-67-7

• 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
• 中文名称: 2-(4-苯基丁-3-烯基)异吲哚-1,3-二酮
• 英文名称: N-(4-phenyl-3-butenyl)phthalimide
• 英文别名: 2-(4-Phenylbut-3-en-1-yl)-1H-isoindole-1,3(2H)-dione；2-(4-phenylbut-3-enyl)isoindole-1,3-dione
• CAS: 143741-67-7
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: DORKDNPQZDMUGX-UHFFFAOYSA-N

物化性质

• 沸点：
  458.4±34.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

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：

  2-(4-苯基丁-3-烯基)异吲哚-1,3-二酮 在 palladium on activated charcoal 氢气 、 甲胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 苯基-4-丁胺
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists

  摘要：

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.

  DOI：

  10.1021/jm9707840
• 作为产物：
  描述：

  (2,6-dimethoxyphenyl)diphenylphosphine 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 2-(4-苯基丁-3-烯基)异吲哚-1,3-二酮
  参考文献：
  名称：

  Role of the through-space 2p-3d overlap effect in the Wittig reaction

  摘要：

  DOI：

  10.1021/jo00155a010

文献信息

• Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines
  作者：Lei Zhao、Xiao Meng、Yifeng Zou、Junsong Zhao、Lili Wang、Lanlan Zhang、Chao Wang

  DOI：10.1021/acs.orglett.1c03210

  日期：2021.11.5

  directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize

  我们在此报告了使用 Ni(II) 催化剂的烯基胺与两种不同的有机卤化物（碘化物和溴化物）的分子间顺芳基烷基化和烯基烷基化。可切割的双齿喹啉酰胺在广泛的定向基团筛选后使用，以实现具有高水平区域、化学和非对映控制的烯烃双官能化。这种通用且实用的方案与α-或β-取代的末端烯烃和内部烯烃兼容，可快速获取带有两个跳跃和邻位立体中心的支链脂肪胺，这些立体中心具有高非对映选择性，否则很难合成。
• Palladium-Catalyzed Direct Arylation of Allylamines with Simple Arenes
  作者：Yichao Lei、Ruiying Qiu、Lingjuan Zhang、Conghui Xu、Yixiao Pan、Xubo Qin、Huanrong Li、Lijin Xu、Yuheng Deng

  DOI：10.1002/cctc.201403019

  日期：2015.4.20

  The Pd(OAc)2‐catalyzed direct CH bond olefination of unreactive arenes with allylamines in the presence of AgOAc was developed. A variety of allylamines including β‐substituted substrates underwent smooth coupling reactions with various arenes to give exclusively the terminal arylation products in high yields with excellent regioselectivities and stereoselectivities. The reaction is compatible with

  将Pd（OAc）2催化的直接Ç 与AgOAc的存在下反应性烯丙胺芳烃H键烯化的开发。包括β-取代的底物在内的各种烯丙胺与各种芳烃进行了平滑偶联反应，从而以高收率独家提供了具有出色的区域选择性和立体选择性的末端芳基化产物。该反应与两个偶联配偶体中的一系列官能团均相容。烯丙基胺底物中的羰基对催化至关重要，观察到的高区域和立体控制归因于羰基O和Pd原子之间的配位。
• 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.
• Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists
  作者：Tomoyuki Yasunaga、Takenori Kimura、Ryo Naito、Toru Kontani、Fumikazu Wanibuchi、Hiroshi Yamashita、Tamako Nomura、Shin-ichi Tsukamoto、Tokio Yamaguchi、Toshiyasu Mase

  DOI：10.1021/jm9707840

  日期：1998.7.1

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.
• Role of the through-space 2p-3d overlap effect in the Wittig reaction
  作者：William E. McEven、John V. Cooney

  DOI：10.1021/jo00155a010

  日期：1983.4