tert-butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)acrylate

• 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: tert-butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)acrylate
• 英文别名: Tert-butyl 2-[(1,3-dioxoisoindol-2-yl)methyl]prop-2-enoate
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: SCGQXWMOIBIGKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)acrylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-((1,3-dioxoisoindolin-2-yl)methyl)acrylic acid
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Olefinic C–H Alkynylation of Acrylamides Using Tosyl-Imide as Directing Group

  摘要：

  The Rh(III)-catalyzed CH alkynylation of acrylamide derivative is realized using a hypervalent alkynyl iodine reagent. The use of a weakly coordinating directing group proved to be of critical importance. This reaction displays broad functional group tolerance and high efficiency, which opens a new synthetic pathway to access functionalized 1,3-enyne skeletons.

  DOI：

  10.1021/ol502984g
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 tert-butyl 2-hydroxymethylacrylate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)acrylate
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Olefinic C–H Alkynylation of Acrylamides Using Tosyl-Imide as Directing Group

  摘要：

  The Rh(III)-catalyzed CH alkynylation of acrylamide derivative is realized using a hypervalent alkynyl iodine reagent. The use of a weakly coordinating directing group proved to be of critical importance. This reaction displays broad functional group tolerance and high efficiency, which opens a new synthetic pathway to access functionalized 1,3-enyne skeletons.

  DOI：

  10.1021/ol502984g

文献信息

• Enantioselective Rhodium Enolate Protonations. A New Methodology for the Synthesis of β²-Amino Acids
  作者：Mukund P. Sibi、Hiroto Tatamidani、Kalyani Patil

  DOI：10.1021/ol050630b

  日期：2005.6.1

  [reaction: see text] Rhodium-catalyzed conjugate addition of an aryl boronic acid to alpha-methylamino acrylates followed by enantioselective protonation of the oxa-pi-allylrhodium intermediate provides access to aryl-substituted beta(2)-amino acids. The impact of the different variables of the reaction on the levels of enantioselectivity has been assessed.

  [反应：见正文]芳基硼酸向α-甲基氨基丙烯酸酯的铑催化共轭加成，然后氧杂-π-烯丙基铑中间体的对映选择性质子化，提供了被芳基取代的β（2）-氨基酸的途径。已经评估了反应的不同变量对对映选择性水平的影响。
• Preparation of Tetrasubstituted Olefins Using Mono or Double Aerobic Direct C–H Functionalization Strategies: Importance of Steric Effects
  作者：Nicolas Gigant、François Quintin、Jan-E. Bäckvall

  DOI：10.1021/acs.joc.5b00148

  日期：2015.3.6

  A novel protocol for the synthesis of tetrasubstituted olefins through a biomimetic approach has been explored. Both mono- and diarylations were performed under ambient oxygen pressure, giving a range of highly hindered tetrasubstituted alkenes. For diarylation of disubstituted substrates, it was demonstrated that the second arylation is the rate-limiting step of the overall transformation.
• Enantioselective H-Atom Transfer Reactions: A New Methodology for the Synthesis ofβ2-Amino Acids
  作者：Mukund P. Sibi、Kalyani Patil

  DOI：10.1002/anie.200353000

  日期：2004.2.27
• Enantioselective Oxidation of Alkenes with Potassium Permanganate Catalyzed by Chiral Dicationic Bisguanidinium
  作者：Chao Wang、Lili Zong、Choon-Hong Tan

  DOI：10.1021/jacs.5b05792

  日期：2015.8.26

  Chiral anion-controlled ion-pairing catalysis was demonstrated to be a wide-ranging strategy that can utilize a variety of cationic metal species. In a similar manner, we envision a complementary strategy using chiral cation in partnership with inorganic anionic metal salts. Herein, we report a chiral dicationic bisguanidinium-catalyzed asymmetric oxidation reaction of alkenes with potassium permanganate. Chiral induction is attributed to ion-pairing interaction between chiral cation and enolate anion. The success of the current permanganate oxidation reaction together with mechanistic insights should provide inspiration for expansion to other anionic metal salts and would open up new paradigms for asymmetric transition metal catalysis, phase-transfer catalysis, and ion-pairing catalysis.