3-cyclohexyl-3,6-dihydro-1,2-dioxine | 681280-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: 3-cyclohexyl-3,6-dihydro-1,2-dioxine
• CAS: 681280-85-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: RCVRAHHTMNSHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclohexyl-3,6-dihydro-1,2-dioxine 在 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以63%的产率得到2-cyclohexyl-2,5-dihydrofuran
  参考文献：
  名称：

  Triphenylphosphine-Induced Ring Contraction of 1,2-Dioxines

  摘要：

  Triphenylphosphine inserts into the peroxide bond of 1,2-dioxines, initiating ring contraction with loss of triphenylphosphine oxide. This process yields dihydrofuran oxides in 54-97% yield from oxirenyl[2,3-c] [1,2]dioxines and dihydrofurans from 3,6-dihydro-1,2-dioxines with inversion of stereochemistry at either the 2 or 5 position in the furan product.

  DOI：

  10.1021/jo030330c
• 作为产物：
  描述：

  buta-1,3-dien-1-ylcyclohexane 在 氧气 、 Rose Bengal bis(triethylammonium) salt 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以55%的产率得到3-cyclohexyl-3,6-dihydro-1,2-dioxine
  参考文献：
  名称：

  新型内过氧化物抗疟药：合成，血红素结合和抗疟药活性。

  摘要：

  我们报告了一系列新型环氧内过氧化物化合物的合成，这些化合物可以从简单的起始原料通过一到三个步骤以高收率制备。这些化合物中的一些在体外抑制恶性疟原虫的生长。结构活性研究表明，被饱和环状部分双取代的内过氧化物环是药效团。为了研究这些新型抗疟疾化合物作用的分子基础，我们研究了它们与氧化和还原形式的血红素相互作用的能力。一些化合物以类似于氯喹和其他4-氨基喹啉的方式与氧化血红素相互作用，而一些化合物则与还原的血红素相互作用。但是，抗疟疾效力水平与这些活动并没有很好的相关性，

  DOI：

  10.1021/jm0305319

文献信息

• Ring-Opening of Unsymmetrical 1,2-Dioxines Using Cobalt(II) Salen Complexes
  作者：Ben W. Greatrex、Dennis K. Taylor

  DOI：10.1021/jo040241f

  日期：2005.1.1

  The regioselectivity of the metal-catalyzed ring opening of unsymmetrical 1,2-dioxines to cis-γ-hydroxyenones was investigated using two different Co(II) salen complexes. Regioselectivity was determined by direct examination of the enone ratios and by derivitization with a stabilized phosphorus ylide. The steric influence of the substituents on the 1,2-dioxine was the primary influence on regioselectivity

  使用两种不同的Co（II）salen配合物，研究了不对称1,2-二恶英在金属催化的开环中对顺式-γ-羟基烯酮的区域选择性。区域选择性是通过直接检查烯酮比率和通过稳定化的磷酰内酯衍生化来确定的。取代基对1,2-二恶英的空间影响是对区域选择性的主要影响。温度起的作用很小。但是，可以使用溶剂和Co（II）配合物的选择来轻微影响所选底物重排的结果。讨论了反应选择性的起源。
• Osmium Catalyzed Dihydroxylation of 1,2-Dioxines:  A New Entry for Stereoselective Sugar Synthesis
  作者：Tony V. Robinson、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo060949p

  日期：2006.9.1

  A series of 3,6-substituted 3,6-dihydro-1,2-dioxines were dihydroxylated with osmium tetroxide to furnish 1,2-dioxane-4,5-diols (peroxy diols) in yields ranging from 33% to 98% and with de values not less than 90%. The peroxy diols were then reduced to generate a stereospecific tetraol core with R, R, S, S or "allitol" stereochemistry. The peroxy diols and their acetonide derivatives were also ring-opened with Co(II) salen complexes to give novel hydroxy ketones in 77-100% yield, including the natural sugar psicose. Importantly, preliminary work on the catalytic asymmetric ring-opening of meso-peroxy diols using the Co(II) Jacobsens's catalyst indicates that asymmetric sugar synthesis from 1,2-dioxines is possible.
• A Domino Ring-Opening/Epoxidation of 1,2-Dioxines
  作者：Ben W. Greatrex、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo0303315

  日期：2004.4.1

  When allowed to react with alkaline hydrogen peroxide, monocyclic 1,2-dioxines ring-open to their isomeric gamma-hydroxyenone intermediates which are rapidly epoxidized to afford trans-4-hydroxy-2,3-epoxyketones in 21-81% yield. In the case of meso-1,2-dioxines, Co(II) complex catalyzed asymmetric ring-opening of the 1,2-dioxine may be employed to furnish enantioenriched epoxides.
• Novel endoperoxides: Synthesis and activity against Candida species
  作者：Peter Macreadie、Thomas Avery、Ben Greatrex、Dennis Taylor、Ian Macreadie

  DOI：10.1016/j.bmcl.2005.10.101

  日期：2006.2

  Fifteen new endoperoxides have been synthesised and tested for activity against pathogenic Candida species. These endoperoxides can be prepared in high yields, in one to three steps, from inexpensive starting materials. Despite chemical and structural similarities, their inhibitory activity against Candida growth varied greatly from one endoperoxide to another, and one species to another. This study of susceptibility to endoperoxide compounds presented here may lead to the development of potent new antifungal agents. (c) 2006 Published by Elsevier Ltd.
• Novel Endoperoxide Antimalarials:  Synthesis, Heme Binding, and Antimalarial Activity
  作者：Dennis K. Taylor、Thomas D. Avery、Ben W. Greatrex、Edward R. T. Tiekink、Ian G. Macreadie、Peter I. Macreadie、Adam D. Humphries、Martha Kalkanidis、Emma N. Fox、Nectarios Klonis、Leann Tilley

  DOI：10.1021/jm0305319

  日期：2004.3.1

  We report the synthesis of a series of novel epoxy endoperoxide compounds that can be prepared in high yields in one to three steps from simple starting materials. Some of these compounds inhibit the growth of Plasmodium falciparum in vitro. Structure-activity studies indicate that an endoperoxide ring bisubstituted with saturated cyclic moieties is the pharmacophore. To study the molecular basis of

  我们报告了一系列新型环氧内过氧化物化合物的合成，这些化合物可以从简单的起始原料通过一到三个步骤以高收率制备。这些化合物中的一些在体外抑制恶性疟原虫的生长。结构活性研究表明，被饱和环状部分双取代的内过氧化物环是药效团。为了研究这些新型抗疟疾化合物作用的分子基础，我们研究了它们与氧化和还原形式的血红素相互作用的能力。一些化合物以类似于氯喹和其他4-氨基喹啉的方式与氧化血红素相互作用，而一些化合物则与还原的血红素相互作用。但是，抗疟疾效力水平与这些活动并没有很好的相关性，