(Z)-N-(戊-2-烯-1-基)邻苯二甲酰亚胺 | 89351-97-3

• 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
• 中文名称: (Z)-N-(戊-2-烯-1-基)邻苯二甲酰亚胺
• 英文名称: (Z)-N-(pent-2-ene-1-yl)phthalimide
• 英文别名: cis-N-(pent-2-en-1-yl)phthalimide；N-((Z)-pent-2-enyl)phthalimide；2-[(Z)-pent-2-enyl]isoindole-1,3-dione
• CAS: 89351-97-3
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: QGTHJMPVMWOZAV-UTCJRWHESA-N

物化性质

• 沸点：
  125 °C(Press: 15 Torr)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-(戊-2-烯-1-基)邻苯二甲酰亚胺 在 一水合肼 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以74%的产率得到(Z)-pent-2-enamine hydrochloride
  参考文献：
  名称：

  N-Alkenyl and cycloalkyl carbamates as dual acting histamine H3 and H4 receptor ligands

  摘要：

  Previous studies have shown that several imidazole derivatives posses affinity to histamine H-3 and H-4 receptors. Continuing our study on structural requirements responsible for affinity and selectivity for H-3/H-4 receptor subtypes, two series of 3-(1H-imidazol-4-yl) propyl carbamates were prepared: a series of unsaturated alkyl derivatives (1-9) and a series possessing a cycloalkyl group different distances to the carbamate moiety (10-13). The compounds were tested for their affinities at the human histamine H3 receptor, stably expressed in CHO-K1 cells. Compounds 1, 2, 5-7, 10-13 were investigated for their affinities at the human histamine H-4 receptor co-expressed with G alpha(i2) and G beta(1)gamma(2) subunits in Sf9 cells. To expand the pharmacological profile, compounds were further tested for their H3 receptor antagonist activity on guinea pig ileum and in vivo after oral administration to mice. All tested compounds exhibited good affinity for the human histamine H-3 receptor with K-i values in the range from 14 to 194 nM. All compounds were active in vivo after peroral administration (p.o.) to Swiss mice, thus demonstrating their ability to cross the blood-brain barrier. The most potent H-3 receptor ligand of these series was compound 5, 3-(1H-imidazol-4-yl) propyl pent-4-enylcarbamate with the highest affinity (K-i = 14 nM). Additionally, compound 3 showed remarkable central nervous system (CNS) H3R activity, increasing the N-tau-methylhistamine levels in mice with an ED50 value of 0.55 mg/kg, p.o. evidencing therefore, a twofold increase of inverse agonist/antagonist potency compared to the reference inverse agonist/antagonist thioperamide. In this study, the imidazole propyloxy carbamate moiety was kept constant. The different lipophilic moieties connected to the carbamate functionality in the eastern part of the molecule had a range of influences on the human H-4 receptor affinity (154-1326 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.046
• 作为产物：
  描述：

  顺-2-戊烯醇 在 三溴化磷 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (Z)-N-(戊-2-烯-1-基)邻苯二甲酰亚胺
  参考文献：
  名称：

  超越两亲平衡：改变亚基立体化学会改变 Nylon-3 聚合物的成孔活性

  摘要：

  据报道，两亲性尼龙 3 聚合物可模仿天然抗菌肽的生物活性，具有高效的抗菌能力和对真核细胞的最小毒性。由亲水和亲脂亚基的比例决定的两亲平衡被认为是尼龙 3 聚合物和许多其他抗菌聚合物实现这种活性特征的最重要特征之一。疏水性不足通常与针对细菌的弱活性相关，而疏水性过度则与对真核细胞的高毒性相关。为了探究两亲平衡以外的因素是否会影响聚合物活性，我们合成并评估了具有两个立体异构亚基的新型尼龙-3 聚合物，每个亚基均带有乙基侧链和氨甲基侧链。预计仅立体化学不同的亚基对两亲平衡的贡献相同，但我们观察到立体化学差异与生物活性谱的显着变化相关。亚基立体化学对抗菌活性影响不大，但破坏真核细胞膜的能力差异很大。平面脂质双层和合成脂质体的实验表明，真核细胞膜破坏是由聚合物介导的大孔形成引起的。总的来说，我们的结果表明，两亲平衡以外的因素也会影响合成聚合物的膜活性。立体化学不同的亚基可能具有不同的构象倾向，这可能

  DOI：

  10.1021/jacs.0c12731

文献信息

• A Cooperative Strategy for the Highly Selective Intermolecular Oxycarbonylation Reaction of Alkenes using a Palladium Catalyst
  作者：Ming Li、Feng Yu、Xiaoxu Qi、Pinhong Chen、Guosheng Liu

  DOI：10.1002/anie.201607248

  日期：2016.10.24

  terminal and internal alkenes has been designed. The electrophilic reagent, hypervalent iodine, plays a key role in this process by activating the alkene C=C bond for nucleophilic addition of the palladium catalyst. This process generates an iodonium‐containing palladium species which undergoes CO insertion. The new approach, intermolecular oxycarbonylaton reactions of alkenes, has been achieved and

  设计了一种新型的末端和内部烯烃分子间官能化方法。亲电子试剂，高价碘，在此过程中起关键作用，它通过激活烯的C = C键来亲核加成钯催化剂。这个过程产生了含碘的钯物质，该钯物质经历了CO的插入。已经实现并在温和的反应条件下进行了烯烃的分子间氧羰基质子反应这一新方法，以产生具有优异效率和区域和非对映选择性的相应β-氧羰基酸。
• Stereoselective iron-catalyzed alkyne hydrogenation in ionic liquids
  作者：Tim N. Gieshoff、Alice Welther、Michael T. Kessler、Martin H. G. Prechtl、Axel Jacobi von Wangelin

  DOI：10.1039/c3cc49679a

  日期：——

  Iron(0) nanoparticles in ionic liquids (ILs) have been shown to catalyse the semi-hydrogenation of alkynes. In the presence of a nitrile-functionalised IL or acetonitrile, stereoselective formation of (Z)-alkenes was observed. The biphasic solvent system allowed facile separation and re-use of the catalyst.

  在离子液体（ILs）中，铁(0)纳米颗粒已被证明可以催化炔烃的半氢化。在含有腈基功能化的离子液体或乙腈的情况下，观察到了立体选择性生成(Z)-烯烃。双相溶剂系统便于催化剂的分离和再使用。
• [EN] EFFICIENT METHODS FOR Z- OR CIS-SELECTIVE CROSS-METATHESIS<br/>[FR] PROCÉDÉS EFFICACES DE MÉTATHÈSE CROISÉE Z-SÉLECTIVE OU CIS-SÉLECTIVE
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2011097642A1

  公开（公告）日：2011-08-11

  The present invention generally relates to methods for performing metathesis reactions, including cross-metathesis reactions. Methods described herein exhibit enhanced activity and stereoselectivity, relative to known methods, and are useful in the synthesis of a large assortment of biologically and therapeutically significant agents.

  本发明通常涉及进行重要反应的方法，包括交叉重要反应。本文描述的方法相对于已知方法表现出增强的活性和立体选择性，并且在合成大量生物学和治疗上重要的药物方面非常有用。
• Alkenylcopper Derivatives; 21^1,2. Synthesis of Allylic Amides and Amines by Amidomethylation of Alkenyl-Copper and -Cuprate Reagents
  作者：C. Germon、A. Alexakis、J. F. Normant

  DOI：10.1055/s-1984-30725

  日期：——
• GERMON, C.;ALEXAKIS, A.;NORMANT, F., SYNTHESIS, BRD, 1984, N 1, 40-43
  作者：GERMON, C.、ALEXAKIS, A.、NORMANT, F.

  DOI：——

  日期：——