bis(2,2,2-trifluoroethyl) 2-(1,3-dioxoisoindolin-2-yl)cyclopropane-1,1-dicarboxylate | 1446102-97-1

• 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: bis(2,2,2-trifluoroethyl) 2-(1,3-dioxoisoindolin-2-yl)cyclopropane-1,1-dicarboxylate
• 英文别名: 2-Phthalimidylcyclopropane-1,1-dicarboxylic acid bis(2,2,2-trifluoroethyl) ester；bis(2,2,2-trifluoroethyl) 2-(1,3-dioxoisoindol-2-yl)cyclopropane-1,1-dicarboxylate
• CAS: 1446102-97-1
• 化学式: C₁₇H₁₁F₆NO₆
• 分子量: 439.268
• InChiKey: GSEOIVPOZUBGEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis(2,2,2-trifluoroethyl) 2-(1,3-dioxoisoindolin-2-yl)cyclopropane-1,1-dicarboxylate 在 potassium carbonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.33h， 生成 dimethyl 2-(2-(1,3-dioxoisoindolin-2-yl)-2-(1H-indol-3-yl)ethyl)malonate
  参考文献：
  名称：

  Catalytic Friedel–Crafts Reaction of Aminocyclopropanes

  摘要：

  A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups and substitution patterns. In the case of C3-substituted indoles, C2 alkylation was observed. The reaction gives a rapid access to gamma amino acid derivatives present in numerous bioactive molecules.

  DOI：

  10.1021/ol401616a
• 作为产物：
  描述：

  bis(2,2,2-trifluoroethyl) malonate 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 bis(2,2,2-trifluoroethyl) 2-(1,3-dioxoisoindolin-2-yl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Catalytic Friedel–Crafts Reaction of Aminocyclopropanes

  摘要：

  A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups and substitution patterns. In the case of C3-substituted indoles, C2 alkylation was observed. The reaction gives a rapid access to gamma amino acid derivatives present in numerous bioactive molecules.

  DOI：

  10.1021/ol401616a

文献信息

• Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes
  作者：Johannes Preindl、Shyamal Chakrabarty、Jérôme Waser

  DOI：10.1039/c7sc03197a

  日期：——

  Many abundant and highly bioactive natural alkaloids contain an indolizidine skeleton. A simple, high yielding method to synthesize this scaffold from N-heterocycles was developed. A wide range of pyridines, quinolines and isoquinolines reacted with Donor-Acceptor (DA)-aminocyclopropanes via an ytterbium(III) catalyzed [3+2] annulation reaction to give tetrahydroindolizine derivatives. The products

  许多丰富且具有高生物活性的天然生物碱都含有吲哚并立啶骨架。开发了一种简单，高产的方法，可从N-杂环合成该支架。各种吡啶，喹啉和异喹啉通过Don（III）催化的[3 + 2]环化反应与施主-受体（DA）-氨基环丙烷反应，得到四氢吲哚嗪衍生物。获得具有高非对映选择性（dr> 20：1）的产物作为抗异构体。另外，形成的缩醛可以通过形成亚胺，然后还原或添加亲核试剂而容易地转化为仲胺和叔胺。这种转化构成了贫电子的六元杂环通过DA环丙烷的[3 + 2]环芳烃脱芳香化作用的第一个例子。
• Annulation Reactions of Donor–Acceptor Cyclopropanes with (1-Azidovinyl)benzene and 3-Phenyl-2<i>H</i>-azirine
  作者：Joanne E. Curiel Tejeda、Lauren C. Irwin、Michael A. Kerr

  DOI：10.1021/acs.orglett.6b02409

  日期：2016.9.16

  Under the influence of heat and Lewis acid, donor/acceptor cyclopropanes underwent annulation reactions with (1-azidovinyl)benzene and 3-phenyl-2H-azirine to form an unusual azabicyclic scaffold with an imbedded aziridine. The mechanism of reaction is believed to proceed via a vinyl nitrene intermediate.

  在热和路易斯酸的影响下，供体/受体环丙烷与（1-叠氮基乙烯基）苯和3-苯基-2 H-叠氮基发生环化反应，形成一种具有嵌入的氮丙啶的不寻常的氮杂双环骨架。据信反应机理是通过乙烯基腈中间体进行的。