(1S,5R)-2,8-dioxabicyclo<3.3.0>octan-3-one | 174590-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (1S,5R)-2,8-dioxabicyclo<3.3.0>octan-3-one
• 英文别名: (3aR,6aS)-3,3a,4,6a-tetrahydro-2H-furo[2,3-b]furan-5-one
• CAS: 174590-88-6
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: IADWRRHAUNBWTI-XINAWCOVSA-N

物化性质

• 沸点：
  263.0±13.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,5S,7RS)-7-phenylseleno-2,8-dioxabicyclo<3.3.0>octan-3-one 在 palladium on activated charcoal 吡啶 、 p-nitrophenyl-2-benzenesulfonyl-3-oxaziridine 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.25h， 生成 (1S,5R)-2,8-dioxabicyclo<3.3.0>octan-3-one
  参考文献：
  名称：

  Synthesis of (1S,5R)-2,8- Dioxabicyclo[3.3.0]octan-3-one from Its Enantiomer: A Subunit of Clerodane Derivatives

  摘要：

  2,8-dioxabicyclo[3.3.0]octan-3-one 的(1S,5R)对映体是通过微生物介导的相应双环前体的 Baeyer-Villiger 氧化反应，从其(1R,5S)对映体开始，经过七步合成制备的。这种内酯是合成烯丙基衍生物的一种有潜在价值的手性结构单元。

  DOI：

  10.1055/s-1995-4132

文献信息

• Microbiological transformations. 25. Enantioselective baeyer-villiger oxidation as a tool for the synthesis of enantiopure bicyclic furofuran and pyrofuran chirons.
  作者：Frédéric Petit、Roland Furstoss

  DOI：10.1016/s0957-4166(00)80245-1

  日期：1993.6

  Several bicyclic [n.2.0] ketones were submitted to enzymatic Baeyer-Villiger oxidation and provided the corresponding regioisomeric lactones showing high enantiopurities. These products could be used as interesting chirons for the synthesis of various natural compounds. The absolute configurations of the obtained lactones were assigned using circular dichroism measurements.

  几种双环[n.2.0]酮被进行酶Baeyer-Villiger氧化，并提供了显示高对映体纯度的相应区域异构内酯。这些产物可用作合成各种天然化合物的有趣的螯合物。使用圆二色性测量来分配所获得的内酯的绝对构型。
• Formaldehyde SAMP-Hydrazone as a Neutral Formyl Anion Equivalent: Asymmetric Synthesis of Substituted β-Formyl δ-Lactones and Furofuran Lactones
  作者：Dieter Enders、Juan Vázquez、Gerhard Raabe

  DOI：10.1002/(sici)1099-0690(200003)2000:6<893::aid-ejoc893>3.0.co;2-u

  日期：2000.3

  β-formyl δ-lactones 5 (de ≥ 98%, ee = 80-95%) and 4-substituted furofuran lactones 6 (de ≥ 98%, ee = 80->98%) in acceptable overall yields is reported. Key steps of the new procedure are an asymmetric Michael addition of formaldehyde SAMP-hydrazone (1) to 5,6-dihydro-2H-pyran-2-one (2) under neutral conditions, followed by trans-selective α-alkylation and subsequent cleavage of the auxiliary by ozonolysis

  α-β取代的甲酰基δ内酯的有效不对称合成5（DE≥98％，EE = 80-95％）和4-取代的内酯Furofuran型6（德≥98％，EE = 80-> 98％）在报告了可接受的总产量。该新方法的关键步骤是在中性条件下将甲醛SAMP hydr（1）不对称地添加到5,6-二氢-2 H-吡喃-2-酮（2）中，然后进行反式-选择性α-烷基化和随后通过臭氧分解或水解多米诺反应方案裂解助剂。给出的标题化合物的绝对构型基于三种X射线结构分析和NOE测量。
• A new preparation of furo-2,3b furans, and conformational studies by 2D NMR.
  作者：M. Jalali、G. Boussac、J.-Y. Lallemand

  DOI：10.1016/s0040-4039(00)88327-6

  日期：1983.1

  Perhydro furo-2,3-b furan derivatives have been prepared by iodocyclisation of unsaturated lactols. Structure and conformation have been studied by high resolution “COSY” 2D NMR.

  全氢呋喃-2,3-b呋喃衍生物是通过不饱和乳糖醇的碘环化制备的。通过高分辨率“ COSY” 2D NMR研究了结构和构象。
• Diastereo- and enantioselective synthesis of 2,8-dioxabicyclo[3.3.0]octan-3-one derivatives
  作者：Dieter Enders、Juan Vázquez、Gerhard Raabe

  DOI：10.1039/a809611b

  日期：——

  An efficient asymmetric synthesis of 4-substituted (1S,4S,5R)-2,8-dioxabicyclo[3.3.0]octan-3-one derivatives (de 98%, ee = 80–>98%) in good overall yields is reported by a stepwise Michael addition–α-alkylation and subsequent hydrolytic domino reaction protocol employing formaldehyde SAMP-hydrazone as a neutral formyl anion equivalent and 5,6-dihydro-2H-pyran-2-one as a Michael acceptor.

  以甲醛 SAMP-hydrazone 作为中性甲酰阴离子当量，5,6-二氢-2H-吡喃-2-酮作为迈克尔受体，通过逐步迈克尔加成-α-烷基化和随后的水解多米诺反应，高效不对称合成了 4-取代的 (1S,4S,5R)-2,8-二氧杂环[3.3.0]辛烷-3-酮衍生物（de 98%，ee = 80->98%），总产率良好。
• Plant enzymes for bioconversion
  申请人：Bouwmeester Jan Hendrik

  公开号：US20050019882A1

  公开（公告）日：2005-01-27

  The invention provides the use of enzymes derived from plants in biocatalysis. The regio- and stercoselective introduction of an oxygen group into an unactivated organic compound is still a largely unresolved challenge to organic chemistry (Faber, 2000). We have shown that enzymes of Asteraceae species are capable of converting with high regio- and stereospecificity for example sesquiterpene olefins to commercially interesting products.

  本发明提供了植物来源酶在生物催化中的应用。将氧基引入未活化有机化合物中的区域和立体选择性仍然是有机化学中一个基本未解决的挑战（Faber，2000）。我们已经证明，菊科物种的酶能够高度区域和立体特异性地将倍半萜烯烃等转化为商业上有趣的产物。