6-endo-6-ethoxy-8-oxabicyclo<3,2,1>oct-3-en-2-one | 87797-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-endo-6-ethoxy-8-oxabicyclo<3,2,1>oct-3-en-2-one
• 英文别名: rac-6α-ethoxy-8-oxabicyclo[3.2.1]oct-3-en-2-one；6-endo-6-ethoxy-8-oxabicyclo[3,2,1]oct-3-en-2-one；(1S,5S,6S)-6-ethoxy-8-oxabicyclo[3.2.1]oct-3-en-2-one
• CAS: 87797-24-8；89567-18-0
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: CUWSWPRAIJBOOA-CIUDSAMLSA-N

物化性质

• 沸点：
  280.1±40.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-endo-6-ethoxy-8-oxabicyclo<3,2,1>oct-3-en-2-one 在 sodium tetrahydroborate 、 四氧化锇 、 甲基磺酰胺 、 cerium(III) chloride heptahydrate 、 AD-mix β 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 45.0h， 生成 (+)-2α-acetoxy-6α-ethoxy-3β,4β-dihydroxy-1,5-dehydrocycloheptane
  参考文献：
  名称：

  Synthesis of optically active seven-membered 1,5-anhydrocarbasugars and 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes via [5+2] cycloaddition

  摘要：

  [5+2] Cycloaddition followed by asymmetric dihydroxylation procedure have been utilized to prepare novel cyclitols. Accordingly, rac-2 alpha-hydroxy-6 alpha-ethoxy-1,5-anhydro cyclohept-3-ene, 10 derived from [5+2] cycloaddition of 3-oxidopyrylium ylide and vinyl ether has been recognized as a seven-membered carbasugar equivalent and elaborated to 1,4,5-tribenzoyloxy-2-ethoxy cycloheptanes through a flexible, regio- and stereoselective strategy involving Sharpless asymmetric dihydroxylation conditions to resolve the compounds obtained. The structures and relative configurations of newly synthesized (+)-2 alpha-acetoxy-6 alpha-ethoxy-3 beta,4 beta-dihydroxy-1,5-anhydro cycloheptane ((+)-12)); (-)-1 beta,4 beta,5 beta-tribenzoyloxy-6 alpha-ethoxy cycloheptane ((-)-17) and (+)-1 alpha,4 alpha,5 alpha-tribenzoyloxy-6 beta-ethoxy cycloheptane ((+)-17) are unambiguously established by single crystal X-ray analysis and duly supported by H-1 and C-13 NMR spectroscopy data. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.014
• 作为产物：
  描述：

  3-oxido pyrillium betaine 、 乙烯基乙醚 以60%的产率得到6-endo-6-ethoxy-8-oxabicyclo<3,2,1>oct-3-en-2-one
  参考文献：
  名称：

  从 [5+2] Oxidopyrylium-烯烃环负载物立体化学定义的四氢呋喃的实用方法

  摘要：

  贝克曼裂解反应的可行性已扩展到 [5+2] 环加合物，该环加合物源自 3-氧化吡啶鎓甜菜碱与各种烯烃的环加成。裂解后，这些环加合物以高总产率产生立体化学定义的四氢呋喃，作为单一的非对映异构体。

  DOI：

  10.1055/s-2007-973866

文献信息

• Preparation and properties of some phytotoxic 2-benzyloxy-8-oxabicyclo[3.2.1]octane derivatives
  作者：Peter G. Sammes、Leslie J. Street、Peter Kirby

  DOI：10.1039/p19830002729

  日期：——

  The preparation and biological activity of a novel group of herbicides is described. These 2-benzyloxy-8-oxabicyclo[3.2.1]octanes are readily obtained from the cycloadducts formed between various olefins and 3-oxidopyrylium ylides, prepared from 6-acetoxypyran-3(6H)-ones.

  描述了新型除草剂的制备和生物学活性。这些2-苄氧基-8-氧杂双环[3.2.1]辛烷很容易从各种烯烃与3-氧氧化吡啶鎓烷基化物之间形成的环加合物获得，所述环氧化物由6-乙酰氧基吡喃-3（6H）-制备。
• Reductive Studies on 3-Oxidopyrylium-alkene [5 + 2] Cycloadducts: Access to Some Hydroxy Cycloheptenoids
  作者：Arun A. Yadav、Urlam Murali Krishna、Prajakta S. Sarang、Prashant S. Patil、Girish K. Trivedi、Manikrao M. Salunkhe

  DOI：10.1080/00397911.2010.481754

  日期：2011.4.5

  Abstract The scope of nickel boride as a versatile reducing reagent is extended to the 3-oxidopyrylium-alkene [5 + 2] cycloadducts. In this report, we demonstrate that nickel boride is capable of one-pot 1,2- and 1,4-reduction of enones present in the cycloadducts in good yields. Subsequent elaboration of the cycloadducts towards synthesis of functionalized cycloheptenoid derivatives devoid of the oxa-bridge

  摘要硼化镍作为一种通用还原剂的范围扩展到 3-氧化吡啶鎓-烯烃 [5 + 2] 环加合物。在本报告中，我们证明硼化镍能够以良好的收率对环加合物中存在的烯酮进行一锅 1,2- 和 1,4-还原。还探索了随后对环加合物合成没有氧杂桥的官能化环庚烯衍生物的详细说明。
• Sammes, Peter G.; Street, Leslie J., Journal of the Chemical Society. Perkin transactions I, 1983, p. 1261 - 1266
  作者：Sammes, Peter G.、Street, Leslie J.

  DOI：——

  日期：——