2-(2-(4-fluorophenyl)allyl)isoindoline-1,3-dione

• 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-(2-(4-fluorophenyl)allyl)isoindoline-1,3-dione
• 英文别名: 2-[2-(4-Fluorophenyl)prop-2-enyl]isoindole-1,3-dione
• 化学式: C₁₇H₁₂FNO₂
• 分子量: 281.286
• InChiKey: BFENMGQUHKLTDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(4-fluorophenyl)allyl)isoindoline-1,3-dione 在 4-二甲氨基吡啶 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-bromo-N-[2-(4-fluorophenyl)allyl]benzamide
  参考文献：
  名称：

  不饱和酰胺的催化不对称氯环化

  摘要：

  （DHQD）2 PHAL催化不饱和酰胺的不对称氯环化反应，生成恶唑啉和二氢恶嗪衍生物（参见方案）。该反应操作简单，并使用1-2 mol％的市售（DHQD）2 PHAL（氢奎尼丁1,4-萘二甲酰二醚）催化剂。烯烃以及芳族和脂族烯烃取代基的不同取代方式具有良好的耐受性。DCDPH = N，N-二氯-5,5-二苯基乙内酰脲。

  DOI：

  10.1002/anie.201006910
• 作为产物：
  描述：

  4-氟-Alpha-甲基苯乙烯 在 N-溴代丁二酰亚胺(NBS) 、 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 2-(2-(4-fluorophenyl)allyl)isoindoline-1,3-dione
  参考文献：
  名称：

  2-芳基烯丙基邻苯二甲酰亚胺的铱的高对映选择性催化氢化。

  摘要：

  提出了铱催化的2-芳基烯丙基邻苯二甲酰亚胺的不对称氢化，以提供对映体富集的β-芳基-β-甲基胺。最近开发的Ir-MaxPHOX催化剂用于该对映选择性转化。温和的反应条件和邻苯二甲酰亚胺基团的可行去除使得该催化方法易于扩展，并且对于提供手性胺具有极大的兴趣。（R）-酪蛋白，OTS514和对映体富集的3-甲基二氢吲哚的正式合成例证了这种新方法的重要性。

  DOI：

  10.1021/acs.orglett.9b03865

文献信息

• Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides
  作者：Albert Cabré、Elia Romagnoli、Pol Martínez-Balart、Xavier Verdaguer、Antoni Riera

  DOI：10.1021/acs.orglett.9b03865

  日期：2019.12.6

  The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The

  提出了铱催化的2-芳基烯丙基邻苯二甲酰亚胺的不对称氢化，以提供对映体富集的β-芳基-β-甲基胺。最近开发的Ir-MaxPHOX催化剂用于该对映选择性转化。温和的反应条件和邻苯二甲酰亚胺基团的可行去除使得该催化方法易于扩展，并且对于提供手性胺具有极大的兴趣。（R）-酪蛋白，OTS514和对映体富集的3-甲基二氢吲哚的正式合成例证了这种新方法的重要性。
• <i>N</i>-Bromoimide/DBU Combination as a New Strategy for Intermolecular Allylic Amination
  作者：Ying Wei、Fushun Liang、Xintong Zhang

  DOI：10.1021/ol402287n

  日期：2013.10.18

  Allylic amination reactions of alkenes, with an NBP (N-bromophthalimide) or NBS (N-bromosuccinimide)/DBU combination, were developed, in which both internal and external nitrogen nucleophiles can be installed directly. Dual activation of NBS or NBP by DBU leads to more electrophilic bromine and more nucleophilic nitrogen atoms simultaneously. This protocol may provide a novel and complementary access

  烯烃的烯丙基胺化反应中，与NBP（Ñ -bromophthalimide）或NBS（ñ溴代琥珀酰亚胺）/ DBU组合，被开发，其中内部和外部氮亲核试剂可以直接安装。DBU对NBS或NBP的双重激活会同时产生更多的亲电子溴和更多的亲核氮原子。该方案可以在温和条件下提供新颖和互补的烯丙基胺化途径。
• 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.
• Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines
  作者：Zhiyang Yan、Bin Sun、Panyi Huang、Haiyun Zhao、Hao Ding、Weike Su、Can Jin

  DOI：10.1016/j.cclet.2021.09.067

  日期：2022.4

  An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions

  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。