3-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-yl]propyl 2,2,5-trimethyl-1,3-dioxane-5-carboxylate | 1032997-14-0

• 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: 3-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-yl]propyl 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• CAS: 1032997-14-0
• 化学式: C₁₉H₂₅NO₇
• 分子量: 379.41
• InChiKey: NUMWDQGTRSOCLJ-KPWCQOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-yl]propyl 2,2,5-trimethyl-1,3-dioxane-5-carboxylate 以 甲苯 为溶剂， 以98%的产率得到3-(2,5-Dioxopyrrol-1-yl)propyl 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
  参考文献：
  名称：

  Segment Block Dendrimers via Diels−Alder Cycloaddition

  摘要：

  Segment block dendrimers consisting of polyester and polyaryl ether dendrons were synthesized using reagent free Diels-Alder cycloaddition reactions. Three generations of furan functionalized polyaryl ether dendrons were reacted with maleimide functionalized polyester dendrons of the same generation to obtain segment block dendrimers in good yields. The thermoreversible nature of these macromolecules was investigated by subjecting them to elevated temperatures in the presence of anthracene as a scavenger diene.

  DOI：

  10.1021/ol800553t
• 作为产物：
  描述：

  exo-3a,4,7,7a-tetrahydro-2-(3-hydroxypropyl)-4,7-epoxy-1H-isoindole-1,3(2H)-dione 、 2,2,5-trimethyl-1,3-dioxane-5-carboxylic anhydride 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到3-[(3aR,4S,7R,7aS)-1,3-dioxo-3a,4,7,7a-tetrahydro-4,7-epoxyisoindol-2-yl]propyl 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
  参考文献：
  名称：

  通过Diels–Alder“点击”反应进行的Dendronized聚合物

  摘要：

  使用狄尔斯-阿尔德“点击”反应，开发了一种用于合成包含树枝状基团作为侧链的聚合物的模块化方法。为此，合成了带有蒽基作为反应性侧链的苯乙烯基聚合物。合成了第一至第三代在焦点处含有呋喃保护的马来酰亚胺基团的聚酯树枝状分子。含蒽的聚合物和潜在反应性树突之间的简便，无试剂的热Diels-Alder环加成反应导致聚合物链的定量官能化，从而得到了树突化的聚合物。使用1 H和13监控此功能化步骤的效率C NMR光谱以及FTIR和UV-vis光谱。©2009 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：410–416，2010年

  DOI：

  10.1002/pola.23799

文献信息

• Dendronized polymers via Diels-Alder “click” reaction
  作者：Murat Tonga、Nergiz Cengiz、Meliha Merve Kose、Tuna Dede、Amitav Sanyal

  DOI：10.1002/pola.23799

  日期：2010.1.15

  synthesis of polymers containing dendron groups as side chains is developed using the Diels–Alder “click” reaction. For this purpose, a styrene‐based polymer appended with anthracene groups as reactive side chains was synthesized. First through third‐generation polyester dendrons containing furan‐protected maleimide groups at their focal point were synthesized. Facile, reagent‐free, thermal Diels–Alder cycloaddition

  使用狄尔斯-阿尔德“点击”反应，开发了一种用于合成包含树枝状基团作为侧链的聚合物的模块化方法。为此，合成了带有蒽基作为反应性侧链的苯乙烯基聚合物。合成了第一至第三代在焦点处含有呋喃保护的马来酰亚胺基团的聚酯树枝状分子。含蒽的聚合物和潜在反应性树突之间的简便，无试剂的热Diels-Alder环加成反应导致聚合物链的定量官能化，从而得到了树突化的聚合物。使用1 H和13监控此功能化步骤的效率C NMR光谱以及FTIR和UV-vis光谱。©2009 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem 48：410–416，2010年
• Sequence-controlled polymerization using dendritic macromonomers: precise chain-positioning of bulky functional clusters
  作者：Nathalie Baradel、Ozgul Gok、Mirela Zamfir、Amitav Sanyal、Jean-François Lutz

  DOI：10.1039/c3cc43501f

  日期：——

  A simple strategy to insert functional dendrons at precise positions along a linear polymer backbone is reported. Sequence controlled copolymerization of styrene and polyester dendrons containing a maleimide unit at their focal points was utilized to yield such polymers.

  报告中介绍了一种在线性聚合物骨架的精确位置插入功能性树枝的简单策略。利用苯乙烯和聚酯树枝的序列控制共聚，在其焦点处含有马来酰亚胺单元，从而得到了这种聚合物。
• Diels-Alder Coupled Proppant Binder Resins
  申请人：Battelle Memorial Institute

  公开号：US20170051200A1

  公开（公告）日：2017-02-23

  Methods and materials for sand control in water injection sites are disclosed. Proppant particles may be coated with some particles coated with a diene and other proppant particles coated with a dienophile that would bind the particles through a Diels-Alder reaction. In some other embodiments, proppant particles may be coated with alternating layers of diene and dienophile that would react through a Diels-Alder reaction. The invention may be advantageous for forming underground structures useful in the extraction of hydrocarbons.
• Segment Block Dendrimers via Diels−Alder Cycloaddition
  作者：M. Merve Kose、Gulen Yesilbag、Amitav Sanyal*

  DOI：10.1021/ol800553t

  日期：2008.6.1

  Segment block dendrimers consisting of polyester and polyaryl ether dendrons were synthesized using reagent free Diels-Alder cycloaddition reactions. Three generations of furan functionalized polyaryl ether dendrons were reacted with maleimide functionalized polyester dendrons of the same generation to obtain segment block dendrimers in good yields. The thermoreversible nature of these macromolecules was investigated by subjecting them to elevated temperatures in the presence of anthracene as a scavenger diene.
• Orthogonally “Clickable” Biodegradable Dendrons
  作者：Meliha Merve Kose、Sebla Onbulak、Idil Ipek Yilmaz、Amitav Sanyal

  DOI：10.1021/ma200593r

  日期：2011.4.26

  with thiol containing molecules. Multiarm poly(ethylene glycol) polymer with a maleimide-based reactive focal point was synthesized using such a dendron. Solubilization of a hydrophobic dye, BODIPY-SH, in aqueous solution via conjugation to these reactive multiarm PEGs demonstrate possible applications of such dendrons to design water-soluble scaffolds for drug delivery.

  合成了一种新型的可正交降解的可生物降解的聚酯树枝状分子，并证明了它们的多功能性。这些树突的表面附加有炔基，可以进行有效的Huisgen型“喀哒”环加成反应，而它们的焦点由反应性马来酰亚胺基组成，可以与含硫醇的分子轻松偶联。使用这种树枝状分子合成具有马来酰亚胺基反应性焦点的多臂聚（乙二醇）聚合物。疏水染料BODIPY-SH通过与这些反应性多臂PEG结合而在水溶液中溶解，证明了此类树枝状分子在设计用于药物递送的水溶性支架方面的可能应用。