2-(5-Oxohexyl)-1,3-dioxolane | 24175-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(5-Oxohexyl)-1,3-dioxolane
• 英文别名: 6-(1,3-Dioxolan-2-yl)hexan-2-one
• CAS: 24175-37-9
• 化学式: C₉H₁₆O₃
• mdl: MFCD11553448
• 分子量: 172.224
• InChiKey: XRQVWVDGSDPTCL-UHFFFAOYSA-N

物化性质

• 沸点：
  248.4±15.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 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：

  2-(5-Oxohexyl)-1,3-dioxolane 在 titanium(IV) isopropylate 、 盐酸 、 高氯酸 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.0h， 生成 1-Benzyl-7-methylazepane-2-carbonitrile
  参考文献：
  名称：

  Structure of Alkaloid 275A, a Novel 1-Azabicyclo[5.3.0]decane from a Dendrobatid Frog, Dendrobates lehmanni:  Synthesis of the Tetrahydrodiastereomers

  摘要：

  The principal alkaloid 275A in skins of the Colombian poison frog Dendrobates lehmanni has been identified as the pyrrolo[1,2-alpha ]azepane (1), the first occurrence in nature of this "izidine" system. Tetrahydro-l proved identical to one of the four synthetic diastereomers, 2a-2d, thereby establishing that 1 has the 5Z,10E relative stereochemistry. Alkaloid 1 is often accompanied by other congeners, in particular a 5Z,10Z diastereomer 15, a dihydro analogue 16, and a ketone 17. Such izidines in frogs may arise from dietary ants, as do other classes of izidines.

  DOI：

  10.1021/np0005098
• 作为产物：
  描述：

  2-(3-溴丙基)-1,3-二氧戊环 在 氢氧化钾 、 sodium hydroxide 、 sodium ethanolate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-(5-Oxohexyl)-1,3-dioxolane
  参考文献：
  名称：

  Construction of linear-fused tricyclopentanoids by intramolecular [6 + 2] cycloadditions of fulvenes with enamines

  摘要：

  DOI：

  10.1021/ja00304a065

文献信息

• Formation of Acetals under Rhodium-Catalyzed Hydroformylation Conditions in Alcohols
  作者：Olivier Diebolt、Clément Cruzeuil、Christian Müller、Dieter Vogt

  DOI：10.1002/adsc.201100707

  日期：2012.3

  Hydroformylation of terminal alkenes in alcohol solvents leads to the selective formation of the corresponding acetals. The Xantphos ligand gave the best results as well as acetal selectivities higher than 99% and linear/branched ratios of up to 52 were obtained. The scope of the reaction was studied. Acetals were found to be unreactive under hydroaminomethylation conditions.

  在醇溶剂中末端烯烃的加氢甲酰化导致相应缩醛的选择性形成。Xantphos配体提供了最佳结果，乙缩醛选择性高于99％，线性/支化比高达52。研究了反应范围。发现缩醛在氢氨甲基化条件下不反应。
• Construction of linear-fused tricyclopentanoids by intramolecular [6 + 2] cycloadditions of fulvenes with enamines
  作者：Tse Chong Wu、K. N. Houk

  DOI：10.1021/ja00304a065

  日期：1985.9
• Structure of Alkaloid 275A, a Novel 1-Azabicyclo[5.3.0]decane from a Dendrobatid Frog, <i>Dendrobates </i><i>l</i><i>ehmanni</i>:  Synthesis of the Tetrahydrodiastereomers
  作者：H. Martin Garraffo、Poonam Jain、Thomas F. Spande、John W. Daly、Tappey. H. Jones、Lance J. Smith、Victor E. Zottig

  DOI：10.1021/np0005098

  日期：2001.4.1

  The principal alkaloid 275A in skins of the Colombian poison frog Dendrobates lehmanni has been identified as the pyrrolo[1,2-alpha ]azepane (1), the first occurrence in nature of this "izidine" system. Tetrahydro-l proved identical to one of the four synthetic diastereomers, 2a-2d, thereby establishing that 1 has the 5Z,10E relative stereochemistry. Alkaloid 1 is often accompanied by other congeners, in particular a 5Z,10Z diastereomer 15, a dihydro analogue 16, and a ketone 17. Such izidines in frogs may arise from dietary ants, as do other classes of izidines.