spiro[4.5]dec-2-ene-6,10-dione | 247040-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiro[4.5]dec-2-ene-6,10-dione
• 英文别名: Spiro[4.5]dec-2-ene-6,10-dione
• CAS: 247040-81-9
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: NYAVIESPWYYPKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro[4.5]dec-2-ene-6,10-dione 在 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以53%的产率得到spiro[4.5]deca-2,8-diene-6,7,10-trione
  参考文献：
  名称：

  Access to Dienophilic Ene-Triketone Synthons by Oxidation of Diketones with an Oxoammonium Salt

  摘要：

  Here we describe the oxidation of 1,3-cyclohexanediones with 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt's salt) to generate 5-ene-1,2,4-triones in moderate-to-good (40-80%) yields. This inexpensive oxidant facilitated an unprecedented cascade of oxidation and elimination to yield novel ene-triketones. The reactivity of these products was explored in the Diets-Alder reaction and provided moderate-to-good yields of cycloaddition products. The products described in this study represent unique, densely functionalized, and versatile building blocks for the synthesis of more complex molecules.

  DOI：

  10.1021/ol2030873
• 作为产物：
  描述：

  2,2-di(prop-2-en-1-yl)cyclohexane-1,3-dione 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到spiro[4.5]dec-2-ene-6,10-dione
  参考文献：
  名称：

  通过串联闭环复分解反应合成角稠合三环化合物

  摘要：

  通过使用选择性串联闭环复分解反应，已经开发出一种新颖且高效的角度稠合三轮车方法。

  DOI：

  10.1039/b002136i

文献信息

• Diversity-oriented approach to spirocycles with indole moiety via Fischer indole cyclization, olefin metathesis and Suzuki–Miyaura cross-coupling reactions
  作者：Sambasivarao Kotha、Rashid Ali、Venu Srinivas、Nimita G. Krishna

  DOI：10.1016/j.tet.2014.11.024

  日期：2015.1

  A range of aryl substituted spirocycles containing the indole moiety have been assembled through Claisen rearrangement, Fischer indole cyclization, ring-closing metathesis and the Suzuki–Miyaura cross-coupling reactions. Some of these molecules contain either a spirocyclic system or an indeno[1,2-b]indole framework, which is present in diverse bioactive targets. Here, we have used simple and readily

  通过克莱森重排，费歇尔吲哚环化，闭环易位和铃木-宫浦交叉偶联反应，已组装了一系列含有吲哚部分的芳基取代螺环。这些分子中的一些包含螺环系统或茚并[1,2- b ]吲哚骨架，它们存在于各种生物活性靶标中。在这里，我们使用了简单易用的起始材料来生成螺环化合物库，其中螺环化合物的结构具有吲哚单元。
• Spiro-Annulation <i>via</i> Ring Closing Metathesis Reaction
  作者：Sambasivarao Kotha、Ethirajan Manivannan、Thota Ganesh、Nampally Sreenivasachary、Ashoke Deb

  DOI：10.1055/s-1999-2896

  日期：——

  Various spiro cyclic systems are prepared from β-di-carbonyl compounds and active methylene substrates via palladium catalyzed allylation and ring-closing metathesis (RCM) reaction as key steps.

  各种螺环系统是通过钯催化的烯丙基化和环闭合复分解（RCM）反应，这两个关键步骤从β-二羰基化合物和活泼的亚甲基底物制备而成。
• An Unexpected Directing Effect in the Asymmetric Transfer Hydrogenation of α,α-Disubstituted Ketones
  作者：Rina Soni、John-Michael Collinson、Guy C. Clarkson、Martin Wills

  DOI：10.1021/ol201643v

  日期：2011.8.19

  alpha,alpha-Disubstituted ketones containing an aromatic ring or alkene are reduced in high enantiomeric excess using an asymmetric transfer hydrogenation catalyst. The sense of reduction indicates that the unsaturated region of the ketone adopts a position adjacent to the Ru-bound eta(6)-arene ring in the reduction transition state.
• Development of a One-Pot Four C–C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis
  作者：Anne-Doriane Manick、Farouk Berhal、Guillaume Prestat

  DOI：10.1021/acs.orglett.7b03556

  日期：2018.1.5

  A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).
• Allylic Alkylation and Ring-Closing Metathesis in Sequence:  A Successful Cohabitation of Pd and Ru
  作者：Claire Kammerer、Guillaume Prestat、Thomas Gaillard、David Madec、Giovanni Poli

  DOI：10.1021/ol702694v

  日期：2008.2.1

  An allylic alkylation/ring-closing metathesis domino catalytic process, wherein a palladium and a ruthenium catalyst are concomitantly present in the reaction mixture from the outset of the reaction, is developed. Evidence for Grubbs' catalysts activity in allylic alkylation is also reported.