(1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione
• 英文别名: 3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]oct-3-ene-2,8-dione；rac-(1R,5R,6R,7R)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]oct-3-ene-2,8-dione；(1S,5S,6S,7S)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]oct-3-ene-2,8-dione
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: NNZIYNPPLWPXDN-IMJCEVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione 在 二苯甲酮 作用下， 以 乙腈 为溶剂， 反应 0.03h， 以89%的产率得到
  参考文献：
  名称：

  光化学转化的多维反应筛选作为发现新化学型的工具

  摘要：

  我们开发了一种自动化光化学微流体平台，该平台集成了 1 kW 高压汞蒸气灯，并允许分析脉冲流或制备性连续流反应。在此，我们将讨论使用该平台通过多维反应筛选发现新化学型。我们将强调使用滤光片离散控制波长的能力，从而控制反应结果。

  DOI：

  10.1021/jo500190b
• 作为产物：
  描述：

  甲基苯乙烯 、 3,4,4-三甲氧基-2,5-环己二烯-1-酮 在 camphor-10-sulfonic acid 、 水 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以52%的产率得到(1RS,5RS,6RS,7RS)-3-methoxy-6-methyl-7-phenylbicyclo[3.2.1]-oct-3-ene-2,8-dione
  参考文献：
  名称：

  Multidimensional Screening and Methodology Development for Condensations Involving Complex 1,2-Diketones

  摘要：

  描述了利用复杂环庚烷-1,2-二酮进行的多维度反应筛选。研究结果发现了区域选择性的路易斯酸介导的与取代脲的缩合反应，以及通过有趣的烯丙基钯氢化物异构化过程进行的非对映选择性氢化反应。

  DOI：

  10.1055/s-0029-1218813

文献信息

• Synthesis and Reactivity of Bicyclo[3.2.1]octanoid-Derived Cyclopropanes
  作者：John R. Goodell、Jennifer L. Poole、Aaron B. Beeler、Jeffrey Aubé、John A. Porco

  DOI：10.1021/jo2018922

  日期：2011.12.2

  Photochemical oxa-di-π-methane rearrangement of bicyclo[3.2.1]octanoid scaffolds affords multifunctional, donor–acceptor cyclopropanes. A related photochemical reaction of an iminium ether substrate uncovered an unprecedented aza-di-π-methane rearrangement of a β,γ-unsaturated iminium. Donor–acceptor cyclopropanes have been evaluated as substrates for reactions generating several new chemotypes.

  双环[3.2.1]辛烷支架的光化学氧杂-二-π-甲烷重排提供了多功能的供体-受体环丙烷。亚胺醚底物的相关光化学反应揭示了 β,γ-不饱和亚胺的前所未有的氮杂-二-π-甲烷重排。供体 - 受体环丙烷已被评估为产生几种新化学型的反应的底物。
• Development of an Automated Microfluidic Reaction Platform for Multidimensional Screening: Reaction Discovery Employing Bicyclo[3.2.1]octanoid Scaffolds
  作者：John R. Goodell、Jonathan P. McMullen、Nikolay Zaborenko、Jason R. Maloney、Chuan-Xing Ho、Klavs F. Jensen、John A. Porco、Aaron B. Beeler

  DOI：10.1021/jo901073v

  日期：2009.8.21

  All automated, silicon-based microreactor system has been developed for rapid, low-volume, multidimensional reaction screening. Use of the microfluidic platform to identify transformations of densely functionalized bicyclo[3.2.1]octanoid scaffolds will be described.
• Reaction Discovery Using Microfluidic-Based Multidimensional Screening of Polycyclic Iminium Ethers
  作者：Jennifer L. Treece、John R. Goodell、David Vander Velde、John A. Porco、Jeffrey Aubé

  DOI：10.1021/jo100087h

  日期：2010.3.19

  Polycyclic iminium ethers are ambident electrophilic intermediates that react with a range of nucleophiles in a highly condition-dependent manner to afford densely functionalized lactams. In an effort to expand the scope of reactivity and assist in the generation of new chemotypes from these intermediates, several iminium ethers were Subjected to reaction screening using an automated microfluidics reaction platform. Application of tills approach led to the discovery of several interesting reaction pathways involving the iminium ether intermediates that will be described.
• Multidimensional Screening and Methodology Development for Condensations Involving Complex 1,2-Diketones
  作者：Aaron Beeler、John Porco Jr.、John Goodell、Bo Leng、Tracy Snyder

  DOI：10.1055/s-0029-1218813

  日期：2010.7

  Multidimensional reaction screening with complex cycloheptane-1,2-diones is described. The studies resulted in the discovery of regioselective Lewis acid mediated condensation reactions with substituted ureas, and a diastereoselective hydrogenation process that proceeds through an interesting isomerization of allylpalladium hydride.

  描述了利用复杂环庚烷-1,2-二酮进行的多维度反应筛选。研究结果发现了区域选择性的路易斯酸介导的与取代脲的缩合反应，以及通过有趣的烯丙基钯氢化物异构化过程进行的非对映选择性氢化反应。
• Multidimensional Reaction Screening for Photochemical Transformations as a Tool for Discovering New Chemotypes
  作者：Véronique I. Martin、John R. Goodell、Oscar J. Ingham、John A. Porco、Aaron B. Beeler

  DOI：10.1021/jo500190b

  日期：2014.5.2

  We have developed an automated photochemical microfluidics platform that integrates a 1 kW high-pressure Hg vapor lamp and allows for analytical pulse flow or preparative continuous flow reactions. Herein, we will discuss the use of this platform toward the discovery of new chemotypes through multidimensional reaction screening. We will highlight the ability to discretely control wavelengths with optical

  我们开发了一种自动化光化学微流体平台，该平台集成了 1 kW 高压汞蒸气灯，并允许分析脉冲流或制备性连续流反应。在此，我们将讨论使用该平台通过多维反应筛选发现新化学型。我们将强调使用滤光片离散控制波长的能力，从而控制反应结果。