Triethyl(7-oxa-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraen-3-yl)silane | 1420009-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Triethyl(7-oxa-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraen-3-yl)silane
• CAS: 1420009-74-0
• 化学式: C₁₆H₂₃NOSi
• 分子量: 273.45
• InChiKey: LLTCNQHWECRQOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-碘-3-硝基苯酚 在 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 lithium chloride 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 Triethyl(7-oxa-2-azatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraen-3-yl)silane
  参考文献：
  名称：

  分子内Larock吲哚合成：3,4-融合三环吲哚的制备和Fargesine的全合成

  摘要：

  核心强度：已开发出一种新的通用策略，用于构建3,4-稠合的三环吲哚，这是众多天然产物和生物活性分子的核心结构。该方法涉及一步法分子内Larock吲哚化，并已成功地应用于Fargesine的第一个全合成。

  DOI：

  10.1002/anie.201300571

文献信息

• Intramolecular Larock indole synthesis for the preparation of tricyclic indoles and its application in the synthesis of tetrahydropyrroloquinoline and fargesine
  作者：Yan Gao、Dong Shan、Yanxing Jia

  DOI：10.1016/j.tet.2014.05.108

  日期：2014.8

  A general and efficient strategy for fused tricyclic indoles from substituted 2-halogenanilines via the palladium-catalyzed intramolecular Larock indolization process has been developed. Using this strategy, a number of 3,4- and 3,5-fused indoles with a variety of ring sizes can been prepared. The utility of this method is demonstrated through the synthesis of the known tetrahydropyrrolo[4,3,2-de]quinoline

  已经开发了通过钯催化的分子内Larock吲哚化过程从取代的2-卤代苯胺中稠合三环吲哚的通用和有效策略。使用这种策略，可以制备许多具有各种环尺寸的3，4-和3，5-稠合的吲哚。该方法的实用性通过已知的四氢吡咯并[4,3,2- de ]喹啉10的合成和Fargesine的第一个全合成来证明。
• A Pd(0)-Mediated Indole (Macro)cyclization Reaction
  作者：Steven P. Breazzano、Yam B. Poudel、Dale L. Boger

  DOI：10.1021/ja3121394

  日期：2013.1.30

  Herein we report a systematic study of the Larock indole annulation designed to explore the scope and define the generality of its use in macrocyclization reactions, its use in directly accessing the chloropeptin I versus II DEF ring system as well as key unnatural isomers, its utility for both peptide-derived and more conventional carbon-chain based macrocycles, and its extension to intramolecular cyclizations with formation of common ring sizes. The studies define a powerful method complementary to the Stile or Suzuki cross-coupling reactions for the synthesis of cyclic or macrocyclic ring systems containing an embedded indole, tolerating numerous functional groups and incorporating various (up to 28-membered) ring sizes. As a result of the efforts to expand the usefulness and scope of the reaction, we also disclose a catalytic variant of the reaction, along with a powerful Pd-2(dba)(3)-derived catalyst system, and an examination of the factors impacting reactivity and catalysis.