2,3,4,4-tetrabromo-8-oxabicyclo[3.2.1]octa-2,6-diene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,3,4,4-tetrabromo-8-oxabicyclo[3.2.1]octa-2,6-diene
• 英文别名: (1R,5S)-2,3,4,4-tetrabromo-8-oxabicyclo[3.2.1]octa-2,6-diene
• 化学式: C₇H₄Br₄O
• 分子量: 423.724
• InChiKey: ROCAQAOHQCUSGJ-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,4,4-tetrabromo-8-oxabicyclo[3.2.1]octa-2,6-diene 在 silver nitrate 作用下， 以 水 、 丙酮 为溶剂， 以83%的产率得到3,4-dibromo-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one
  参考文献：
  名称：

  环丙烯的双环[3.2.1]辛烷合成子：亲核加成作用对Cycloadducts的功能化。

  摘要：

  几十年来，已经知道，通过将呋喃或环戊二烯与四氯或四溴环丙烯进行环加成反应，可以容易地获得高度官能化的四卤代双环[3.2.1]辛二烯家族。然而，相对于它们通过羟基烯丙基阳离子加成而衍生的更广为人知的对应物，这些高度功能化的结构单元在合成中的应用仍处于相对未被探索的状态。作为在合成中利用这些高度通用的中间体的第一步，已经进行了将各种亲核试剂添加到卤代核中的研究。已经发现，这些卤化体系以高收率和良好的选择性适合于广泛的官能化。

  DOI：

  10.1021/jo035240m
• 作为产物：
  描述：

  呋喃 、 1,2,3,3-四溴环丙烯 以 1,4-二氧六环 为溶剂， 生成 2,3,4,4-tetrabromo-8-oxabicyclo[3.2.1]octa-2,6-diene
  参考文献：
  名称：

  Stereodivergent Resolution of Oxabicyclic Ketones: Preparation of Key Intermediates for Platensimycin and Other Natural Products

  摘要：

  An improved methodology for the preparation of enantiopure oxabicyclo[3.2.1]octadienes via a stereodivergent resolution is reported. High catalyst control proximal to the oxabridged stereocenter produces readily separable diastereomers in high yield (>92%) and with excellent optical purity (>95% ee). This resolution strategy is amenable to large-scale preparations, and the utility of the resolution was further demonstrated in the asymmetric preparation of a key intermediate used in the synthesis of the antibiotic (-)-platensimycin.

  DOI：

  10.1021/jo4017502

文献信息

• Bicyclo[3.2.1]octane Synthons from Cyclopropenes:  Functionalization of Cycloadducts by Nucleophilic Additions
  作者：Ravi S. Orugunty、Dennis L. Wright、Merle A. Battiste、Richard J. Helmich、Khalil Abboud

  DOI：10.1021/jo035240m

  日期：2004.1.1

  counterparts derived through oxyallyl cation additions. As a first step toward utilizing these highly versatile intermediates in synthesis, a study of the addition of various nucleophiles to the halogenated nucleus has been conducted. It has been found that these halogenated systems are amenable to a wide range of functionalizations in high yields and with good selectivities.

  几十年来，已经知道，通过将呋喃或环戊二烯与四氯或四溴环丙烯进行环加成反应，可以容易地获得高度官能化的四卤代双环[3.2.1]辛二烯家族。然而，相对于它们通过羟基烯丙基阳离子加成而衍生的更广为人知的对应物，这些高度功能化的结构单元在合成中的应用仍处于相对未被探索的状态。作为在合成中利用这些高度通用的中间体的第一步，已经进行了将各种亲核试剂添加到卤代核中的研究。已经发现，这些卤化体系以高收率和良好的选择性适合于广泛的官能化。
• Stereodivergent Resolution of Oxabicyclic Ketones: Preparation of Key Intermediates for Platensimycin and Other Natural Products
  作者：Michael D. VanHeyst、E. Zachary Oblak、Dennis L. Wright

  DOI：10.1021/jo4017502

  日期：2013.10.18

  An improved methodology for the preparation of enantiopure oxabicyclo[3.2.1]octadienes via a stereodivergent resolution is reported. High catalyst control proximal to the oxabridged stereocenter produces readily separable diastereomers in high yield (>92%) and with excellent optical purity (>95% ee). This resolution strategy is amenable to large-scale preparations, and the utility of the resolution was further demonstrated in the asymmetric preparation of a key intermediate used in the synthesis of the antibiotic (-)-platensimycin.
• Efficient synthesis of bicyclo[3.2.1]octane-2,4-diones and their incorporation into potent HPPD inhibitors
  作者：Myriam Baalouch、Alain De Mesmaeker、Renaud Beaudegnies

  DOI：10.1016/j.tetlet.2012.11.081

  日期：2013.2

  Herein we report a very efficient access to a variety of bicyclic 1,3-diones as key intermediates to be incorporated into very potent HPPD inhibitors. In particular, we have developed a one-pot process for the synthesis of the bicyclo[3.2.1]octane-2,4-dione, the parent dione of Bicyclopyrone. (c) 2012 Elsevier Ltd. All rights reserved.