2-[(Z)-2-phenylvinyl]-1H-isoindole-1,3(2H)-dione | 136613-13-3

• 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: 2-[(Z)-2-phenylvinyl]-1H-isoindole-1,3(2H)-dione
• 英文别名: (Z)-N-(2-phenylethenyl)phthalimide；(Z)-2-styrylisoindoline-1,3-dione；N-[(Z)-2-phenylvinyl]phthalimide；(Z)-N-styrylphthalimide；2-[(Z)-2-phenylethenyl]isoindole-1,3-dione
• CAS: 136613-13-3
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: WAYYQTOFXYMTHX-KHPPLWFESA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  426.1±38.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-phenylethyl)phthalimide 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过氧化苯甲酰 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-[(Z)-2-phenylvinyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Benzylphthalimides and Phenethylphthalimides with Thalidomide-Like Activity on the Production of Tumor Necrosis Factor .ALPHA..

  摘要：

  苄基邻苯二甲酰亚胺类化合物（P1P's）和苯乙基邻苯二甲酰亚胺类化合物（P2P's）被发现能够在通过12-O-十四酸酯磷酸酯（TPA）刺激的人类白血病细胞系HL-60中表现出类沙利度胺的活性，促进肿瘤坏死因子（TNF）-α的产生。基于TNF-α产生增强活性，讨论了结构-活性关系。苄基邻苯二甲酰亚胺（P1P-00）表现出的活性弱于沙利度胺，但在苄基的邻位引入甲基（P1P-10）后，其活性增强至与沙利度胺相当的水平。苯乙基邻苯二甲酰亚胺（P2P-00）的活性比沙利度胺更强，其氟化衍生物2-苯乙基-4, 5, 6, 7-四氟-1H-异苯并吡咯-1, 3-二酮（FP2P-00）在极低浓度下表现出强效活性。

  DOI：

  10.1248/bpb.18.1228

文献信息

• Synthesis of Aminocyclobutanes by Iron-Catalyzed [2+2] Cycloaddition
  作者：Florian de Nanteuil、Jérôme Waser

  DOI：10.1002/anie.201303803

  日期：2013.8.19

  Fab Four: An iron‐catalyzed [2+2] cycloaddition furnishes aminocyclobutanes with a broad range of substituents in excellent yields and diastereoselectivities. The products can be obtained on a gram scale and can be further converted to β‐peptide derivatives in a few steps. Furthermore, a [4+2] cycloaddition between an aminocyclobutane and an olefin leads to the corresponding cyclohexylamines.

  第四工厂：铁催化的[2 + 2]环加成反应可提供具有广泛取代基的氨基环丁烷，并具有出色的收率和非对映选择性。这些产物可以克量级获得，并且可以在几个步骤中进一步转化为β-肽衍生物。此外，在氨基环丁烷和烯烃之间的[4 + 2]环加成产生相应的环己胺。
• Photoinduced Addition of Phthalimide to Unactivated Alkynes†
  作者：Francisco Nájera、Rafael García-Segura、Ezequiel Pérez-Inestrosa、Cristóbal Sánchez-Sánchez、Rafael Suau

  DOI：10.1562/2005-05-30-ra-555

  日期：——

  with its conjugated base produces the regioselective hydrophthalimidation of conjugated alkynes. The vinylphthalimide thus obtained is hydrolyzed to the corresponding carbonyl compound. With unconjugated alkynes, the outcome is a double addition of phthalimide to the triple bond. The reaction is assumed to take place via single electron transfer from either the alkyne or the phthalimide anion to the

  摘要 与其共轭碱平衡的光激发邻苯二甲酰亚胺产生共轭炔烃的区域选择性氢化邻苯二甲酰亚胺。如此获得的乙烯基邻苯二甲酰亚胺水解成相应的羰基化合物。对于非共轭炔烃，结果是邻苯二甲酰亚胺双加成到三键上。假设该反应是通过从炔烃或邻苯二甲酰亚胺阴离子到激发的邻苯二甲酰亚胺的单电子转移发生的，这是主要的光处理过程。
• Stereospecific One-pot Synthesis of Enamides and Enimides by the Copper Iodide Promoted Vinylic Substitution
  作者：Takuji Ogawa、Toshiyuki Kiji、Kazuo Hayami、Hitomi Suzuki

  DOI：10.1246/cl.1991.1443

  日期：1991.8

  Enamides and enimides were prepared stereospecifically from vinyl bromides by direct vinylic substitution in the presence of copper salt in aprotic polar solvents.

  在铜盐存在下，通过在非沸腾极性溶剂中直接进行乙烯基取代，以乙烯基溴化物为原料制备了立体定向的酰胺和酰亚胺。
• Ru-Catalyzed Stereoselective Addition of Imides to Alkynes
  作者：Lukas J. Goossen、Mathieu Blanchot、Claus Brinkmann、Käthe Goossen、Ralph Karch、Andreas Rivas-Nass

  DOI：10.1021/jo061966h

  日期：2006.12.1

  A catalyst system formed in situ from bis(2-methylallyl)cycloocta- 1,5-dieneruthenium(II) ((cod)Ru[met](2)), a phosphine, and scandium(III) trifluoromethanesulfonate (Sc-(OTf)(3)) was found to efficiently catalyze the anti-Markovnikov addition of imides to terminal alkynes, allowing mild and atom-economic synthesis of enimides. Depending on the phosphine employed, both the (E)- and the (Z)-isomer can be accessed stereoselectively.
• Synthesis and photophysical properties of<i>N</i>-styrylazinones
  作者：Su-Dong Cho、Jaeyoung Hwang、Ho-Kyun Kim、Heung-Sup Yim、Jeum-Jong Kim、Sang-Gyeong Lee、Yong-Jin Yoon

  DOI：10.1002/jhet.5570440435

  日期：2007.7

  Abstractmagnified imageN‐Styrylazinones and 1‐styrylbenzotriazine were synthesized, and their photophysical properties were investigated. (Z)‐ and/or (E)‐N‐Styrylazinones (or azine) 4 were prepared from the corresponding heterocycles 1 and benzaldehyde (3) by four methods. The absorption maxima of (Z)‐ and/or (E)‐4a‐4j were measured in four solvents. Their absorption maxima showed a moderate dependence upon solvents. The absorption maxima of (Z)‐isomers were blue‐shifted as compared the corresponding (E)‐isomers. Emission maxima, fluorescence band half‐widths, 0,0 transition energies, Stokes shifts, and quantum yields of (Z)‐ and/or (E)‐4a, 4b, 4d, 4e and 4j were measured in organic solvents. The fluorescence spectra show moderate solvatochroism. The fluorescence properties of N‐styrylheterocycles vary with every heterocycles.